FR2619008A1 - Use of synergistins in pharmaceutical or cosmetic anti-acne compositions - Google Patents
Use of synergistins in pharmaceutical or cosmetic anti-acne compositions Download PDFInfo
- Publication number
- FR2619008A1 FR2619008A1 FR8710998A FR8710998A FR2619008A1 FR 2619008 A1 FR2619008 A1 FR 2619008A1 FR 8710998 A FR8710998 A FR 8710998A FR 8710998 A FR8710998 A FR 8710998A FR 2619008 A1 FR2619008 A1 FR 2619008A1
- Authority
- FR
- France
- Prior art keywords
- streptogramin
- synergistin
- mikamycin
- virginiamycin
- pristinamycin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 26
- 230000003255 anti-acne Effects 0.000 title claims abstract description 4
- 239000002537 cosmetic Substances 0.000 title claims description 13
- DAIKHDNSXMZDCU-OUDXUNEISA-N pristinamycin-IIA Natural products CC(C)[C@H]1OC(=O)C2=CCCN2C(=O)c3coc(CC(=O)C[C@H](O)C=C(C)C=CCNC(=O)C=C[C@@H]1C)n3 DAIKHDNSXMZDCU-OUDXUNEISA-N 0.000 claims abstract description 37
- DAIKHDNSXMZDCU-FQTGFAPKSA-N pristinamycin IIA Chemical compound C1C(=O)C[C@H](O)\C=C(/C)\C=C\CNC(=O)\C=C\[C@@H](C)[C@@H](C(C)C)OC(=O)C2=CCCN2C(=O)C2=COC1=N2 DAIKHDNSXMZDCU-FQTGFAPKSA-N 0.000 claims abstract description 22
- YGXCETJZBDTKRY-DZCVGBHJSA-N pristinamycin IA Chemical compound N([C@@H]1C(=O)N[C@@H](C(N2CCC[C@H]2C(=O)N(C)[C@@H](CC=2C=CC(=CC=2)N(C)C)C(=O)N2CCC(=O)C[C@H]2C(=O)N[C@H](C(=O)O[C@@H]1C)C=1C=CC=CC=1)=O)CC)C(=O)C1=NC=CC=C1O YGXCETJZBDTKRY-DZCVGBHJSA-N 0.000 claims abstract description 20
- 108010015791 Streptogramin A Proteins 0.000 claims abstract description 17
- 108010015795 Streptogramin B Proteins 0.000 claims abstract description 17
- 239000004480 active ingredient Substances 0.000 claims abstract description 5
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- MVTQIFVKRXBCHS-SMMNFGSLSA-N N-[(3S,6S,12R,15S,16R,19S,22S)-3-benzyl-12-ethyl-4,16-dimethyl-2,5,11,14,18,21,24-heptaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentazatricyclo[20.4.0.06,10]hexacosan-15-yl]-3-hydroxypyridine-2-carboxamide (10R,11R,12E,17E,19E,21S)-21-hydroxy-11,19-dimethyl-10-propan-2-yl-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.03,7]octacosa-1(27),6,12,17,19,25(28)-hexaene-2,8,14,23-tetrone Chemical compound CC(C)[C@H]1OC(=O)C2=CCCN2C(=O)c2coc(CC(=O)C[C@H](O)\C=C(/C)\C=C\CNC(=O)\C=C\[C@H]1C)n2.CC[C@H]1NC(=O)[C@@H](NC(=O)c2ncccc2O)[C@@H](C)OC(=O)[C@@H](NC(=O)[C@@H]2CC(=O)CCN2C(=O)[C@H](Cc2ccccc2)N(C)C(=O)[C@@H]2CCCN2C1=O)c1ccccc1 MVTQIFVKRXBCHS-SMMNFGSLSA-N 0.000 claims description 32
- JOOMGSFOCRDAHL-XKCHLWDXSA-N pristinamycin-IIB Natural products CC(C)[C@@H]1OC(=O)[C@H]2CCCN2C(=O)c3coc(CC(=O)C[C@@H](O)C=C(C)C=CCNC(=O)C=C[C@H]1C)n3 JOOMGSFOCRDAHL-XKCHLWDXSA-N 0.000 claims description 22
- 108010079780 Pristinamycin Proteins 0.000 claims description 21
- RLNUPSVMIYRZSM-UHFFFAOYSA-N Pristinamycin Natural products CC1OC(=O)C(C=2C=CC=CC=2)NC(=O)C2CC(=O)CCN2C(=O)C(CC=2C=CC(=CC=2)N(C)C)CCN(C)C(=O)C2CCCN2C(=O)C(CC)NC(=O)C1NC(=O)C1=NC=CC=C1O RLNUPSVMIYRZSM-UHFFFAOYSA-N 0.000 claims description 21
- 229960003961 pristinamycin Drugs 0.000 claims description 21
- 208000002874 Acne Vulgaris Diseases 0.000 claims description 18
- 206010000496 acne Diseases 0.000 claims description 18
- 108010034396 Streptogramins Proteins 0.000 claims description 10
- YGXCETJZBDTKRY-UHFFFAOYSA-N Pristinamycin Component I A Natural products CC1OC(=O)C(C=2C=CC=CC=2)NC(=O)C2CC(=O)CCN2C(=O)C(CC=2C=CC(=CC=2)N(C)C)N(C)C(=O)C2CCCN2C(=O)C(CC)NC(=O)C1NC(=O)C1=NC=CC=C1O YGXCETJZBDTKRY-UHFFFAOYSA-N 0.000 claims description 9
- CZZMMEAMWBSORN-UHFFFAOYSA-N Mikamycin B Natural products CCC1NC(=O)C(NC(=O)c2ccccc2O)N(C)OC(=O)C(NC(=O)C3CC(=O)CCN3C(=O)C(Cc4ccc(cc4)N(C)C)N(C)C(=O)C5CCCN5C1=O)c6ccccc6 CZZMMEAMWBSORN-UHFFFAOYSA-N 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- DAIKHDNSXMZDCU-UHFFFAOYSA-N pristinamycin component IIA Natural products C1C(=O)CC(O)C=C(C)C=CCNC(=O)C=CC(C)C(C(C)C)OC(=O)C2=CCCN2C(=O)C2=COC1=N2 DAIKHDNSXMZDCU-UHFFFAOYSA-N 0.000 claims description 8
- 108010080702 Virginiamycin Proteins 0.000 claims description 7
- 239000004188 Virginiamycin Substances 0.000 claims description 6
- 229940041030 streptogramins Drugs 0.000 claims description 6
- 235000019373 virginiamycin Nutrition 0.000 claims description 6
- 229960003842 virginiamycin Drugs 0.000 claims description 5
- FEPMHVLSLDOMQC-UHFFFAOYSA-N virginiamycin-S1 Natural products CC1OC(=O)C(C=2C=CC=CC=2)NC(=O)C2CC(=O)CCN2C(=O)C(CC=2C=CC=CC=2)N(C)C(=O)C2CCCN2C(=O)C(CC)NC(=O)C1NC(=O)C1=NC=CC=C1O FEPMHVLSLDOMQC-UHFFFAOYSA-N 0.000 claims description 5
- 229930192051 Mikamycin Natural products 0.000 claims description 4
- 108010046774 Mikamycin Proteins 0.000 claims description 4
- 229950007764 mikamycin Drugs 0.000 claims description 4
- 239000003581 cosmetic carrier Substances 0.000 claims description 2
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 27
- 229960002227 clindamycin Drugs 0.000 description 15
- KDLRVYVGXIQJDK-AWPVFWJPSA-N clindamycin Chemical compound CN1C[C@H](CCC)C[C@H]1C(=O)N[C@H]([C@H](C)Cl)[C@@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](SC)O1 KDLRVYVGXIQJDK-AWPVFWJPSA-N 0.000 description 15
- 229960003276 erythromycin Drugs 0.000 description 13
- 239000003242 anti bacterial agent Substances 0.000 description 12
- 229940088710 antibiotic agent Drugs 0.000 description 12
- 238000011282 treatment Methods 0.000 description 11
- 238000000034 method Methods 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 6
- 241000186427 Cutibacterium acnes Species 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 230000003902 lesion Effects 0.000 description 5
- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 4
- 229940121375 antifungal agent Drugs 0.000 description 4
- 230000003115 biocidal effect Effects 0.000 description 4
- 239000006071 cream Substances 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 208000035475 disorder Diseases 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- 239000006210 lotion Substances 0.000 description 4
- 235000013336 milk Nutrition 0.000 description 4
- 210000004080 milk Anatomy 0.000 description 4
- -1 orally or topically Chemical compound 0.000 description 4
- 239000003981 vehicle Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 206010034133 Pathogen resistance Diseases 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000004098 Tetracycline Substances 0.000 description 3
- 230000000843 anti-fungal effect Effects 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 239000008267 milk Substances 0.000 description 3
- 239000002674 ointment Substances 0.000 description 3
- 235000019364 tetracycline Nutrition 0.000 description 3
- 150000003522 tetracyclines Chemical class 0.000 description 3
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 229920001214 Polysorbate 60 Polymers 0.000 description 2
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000000051 antiandrogen Substances 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 230000003385 bacteriostatic effect Effects 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 229940082500 cetostearyl alcohol Drugs 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 238000002512 chemotherapy Methods 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 230000003780 keratinization Effects 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 230000000813 microbial effect Effects 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 230000035755 proliferation Effects 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000001587 sorbitan monostearate Substances 0.000 description 2
- 235000011076 sorbitan monostearate Nutrition 0.000 description 2
- 229940035048 sorbitan monostearate Drugs 0.000 description 2
- 229940040944 tetracyclines Drugs 0.000 description 2
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- LEZWWPYKPKIXLL-UHFFFAOYSA-N 1-{2-(4-chlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl}imidazole Chemical compound C1=CC(Cl)=CC=C1COC(C=1C(=CC(Cl)=CC=1)Cl)CN1C=NC=C1 LEZWWPYKPKIXLL-UHFFFAOYSA-N 0.000 description 1
- PNCWHIAZZSDHPU-UHFFFAOYSA-N 2-benzylsulfanylethanamine Chemical compound NCCSCC1=CC=CC=C1 PNCWHIAZZSDHPU-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 244000144725 Amygdalus communis Species 0.000 description 1
- 235000011437 Amygdalus communis Nutrition 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 229920002884 Laureth 4 Polymers 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- BYBLEWFAAKGYCD-UHFFFAOYSA-N Miconazole Chemical compound ClC1=CC(Cl)=CC=C1COC(C=1C(=CC(Cl)=CC=1)Cl)CN1C=NC=C1 BYBLEWFAAKGYCD-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- PCOXSOQWQVRJCH-UHFFFAOYSA-N Pristinamycin IB Chemical compound CC1OC(=O)C(C=2C=CC=CC=2)NC(=O)C2CC(=O)CCN2C(=O)C(CC=2C=CC(NC)=CC=2)N(C)C(=O)C2CCCN2C(=O)C(CC)NC(=O)C1NC(=O)C1=NC=CC=C1O PCOXSOQWQVRJCH-UHFFFAOYSA-N 0.000 description 1
- GBFLZEXEOZUWRN-VKHMYHEASA-N S-carboxymethyl-L-cysteine Chemical compound OC(=O)[C@@H](N)CSCC(O)=O GBFLZEXEOZUWRN-VKHMYHEASA-N 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 206010039792 Seborrhoea Diseases 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- 241000187747 Streptomyces Species 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 239000008168 almond oil Substances 0.000 description 1
- 230000002280 anti-androgenic effect Effects 0.000 description 1
- 229940030495 antiandrogen sex hormone and modulator of the genital system Drugs 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 235000008429 bread Nutrition 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 229960000978 cyproterone acetate Drugs 0.000 description 1
- UWFYSQMTEOIJJG-FDTZYFLXSA-N cyproterone acetate Chemical compound C1=C(Cl)C2=CC(=O)[C@@H]3C[C@@H]3[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 UWFYSQMTEOIJJG-FDTZYFLXSA-N 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229960003913 econazole Drugs 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- SFNALCNOMXIBKG-UHFFFAOYSA-N ethylene glycol monododecyl ether Chemical compound CCCCCCCCCCCCOCCO SFNALCNOMXIBKG-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000003410 keratolytic agent Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229940061515 laureth-4 Drugs 0.000 description 1
- 239000003120 macrolide antibiotic agent Substances 0.000 description 1
- 229940041033 macrolides Drugs 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 229960002509 miconazole Drugs 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
- 229940100691 oral capsule Drugs 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- BYRKDHSWMQLYJB-UHFFFAOYSA-N pristinamycin IC Chemical compound CN1C(=O)C2CCCN2C(=O)C(C)NC(=O)C(NC(=O)C=2C(=CC=CN=2)O)C(C)OC(=O)C(C=2C=CC=CC=2)NC(=O)C2CC(=O)CCN2C(=O)C1CC1=CC=C(N(C)C)C=C1 BYRKDHSWMQLYJB-UHFFFAOYSA-N 0.000 description 1
- 229960003387 progesterone Drugs 0.000 description 1
- 239000000186 progesterone Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 229940055019 propionibacterium acne Drugs 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 208000008742 seborrheic dermatitis Diseases 0.000 description 1
- 210000002374 sebum Anatomy 0.000 description 1
- VIDTVPHHDGRGAF-UHFFFAOYSA-N selenium sulfide Chemical compound [Se]=S VIDTVPHHDGRGAF-UHFFFAOYSA-N 0.000 description 1
- 229960005265 selenium sulfide Drugs 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 229960002180 tetracycline Drugs 0.000 description 1
- 229930101283 tetracycline Natural products 0.000 description 1
- SLYPOVJCSQHITR-UHFFFAOYSA-N tioxolone Chemical compound OC1=CC=C2SC(=O)OC2=C1 SLYPOVJCSQHITR-UHFFFAOYSA-N 0.000 description 1
- 229960003070 tioxolone Drugs 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Molecular Biology (AREA)
- Dermatology (AREA)
- Birds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
La présente invention a pour objet l'utilisation des antibiotiques de la classe des synergistines dans le traitement de l'acné. The subject of the present invention is the use of antibiotics of the synergistin class in the treatment of acne.
On sait que l'acné est une affection cutanée fréquente chez l'adolescent et aussi chez l'adulte. Cette affection est caractérisée par un trouble de la kératinisation des pores des zones séborrhéiques du visage, de la région présternale et du dos. Il en résulte la formation de bouchons cornés avec accumulation de sébum, qui constituent un milieu propice au développement de bactéries qui provoquent une lésion inflammatoire. Le Propionibacterium acnes (P.acnes) est le principal agent bactérien responsable de ces lésions. We know that acne is a common skin condition in adolescents and also in adults. This condition is characterized by a disorder of the keratinization of the pores of the seborrheic areas of the face, the presternal region and the back. This results in the formation of horny plugs with accumulation of sebum, which constitute an environment conducive to the development of bacteria which cause an inflammatory lesion. Propionibacterium acnes (P.acnes) is the main bacterial agent responsible for these lesions.
Les traitements de l'acné visent à combattre soit le trouble de la kératinisation, soit la séborrhée, soit la prolifération microbienne. On a proposé notamment de lutter contre la prolifération microbienne à l'aide d'antibiotiques par voie orale ou locale, souvent sur des périodes très longues allant de 6 mois à 2 ans. Les antibiotiques Les plus couramment utilisés dans ce but sont les tétracyclines et l'érythromycine, par voie bucale ou topique, et la clindamycine par voie topique. Acne treatments aim to combat either the keratinization disorder, or seborrhea, or microbial proliferation. In particular, it has been proposed to combat microbial proliferation using oral or local antibiotics, often over very long periods ranging from 6 months to 2 years. Antibiotics The most commonly used for this purpose are tetracyclines and erythromycin, orally or topically, and clindamycin topically.
Toutefois, les traitements réalisés avec ces antibiotiques présentent des inconvénients. On a observé en particulier l'apparition, dans des proportions importantes, de souches de P.acnès résistantes à la clindamycine. Cette résistance est accompagnée d'une résistance croisée à l'érythromycine. Parallelement, on a noté l'apparition chez les patients traités avec l'érythromycine, de souches résistantes à cet antibiotique et aussi à la clindamycine ; voir par exemple W.Crawford, the Journal of
Investigative Dermatology, 72, 187-190 (1979). On a également noté, chez les patients traités à la clindamycine, l'apparition de souches de P.acnes résistantes non seulement à la clindamycine et à l'érythromycine, mais aussi aux tétracyclines ; voir C.Marino et al., Journal of the American Academy of
Dermatology, vol.6, pages 902-908 (1982).However, the treatments carried out with these antibiotics have drawbacks. In particular, the appearance, in significant proportions, of strains of P. acnès resistant to clindamycin has been observed. This resistance is accompanied by cross resistance to erythromycin. At the same time, the emergence in patients treated with erythromycin of strains resistant to this antibiotic and also to clindamycin was noted; see for example W. Crawford, the Journal of
Investigative Dermatology, 72, 187-190 (1979). It has also been noted, in patients treated with clindamycin, the appearance of P.acnes strains resistant not only to clindamycin and to erythromycin, but also to tetracyclines; see C. Marin et al., Journal of the American Academy of
Dermatology, vol. 6, pages 902-908 (1982).
Des observations analogues ont été faites chez des patients traités à la tétracycline ; voir James J.Leyden et al., Journal of the American
Academy of Dermatology, vol.8, pages 41-45 (1983).Similar observations have been made in patients treated with tetracycline; see James J. Leyden et al., Journal of the American
Academy of Dermatology, vol.8, pages 41-45 (1983).
On sait par ailleurs que les synergistines sont des antibiotiques, isolés de milieux de culture de diverses souches de Streptomyces, constitués par l'association de deux types de facteurs (A et B) appartenant au groupe des
Streptogramines et agissant en synergie. Les facteurs A ont une structure proche de celle des macrolides et les facteurs B sont des heptapeptides cycliques. Chacun des facteurs, pris isolément, a une activité bactériostatique, mais l'association A + B a une activité bactéricide caractérisant un effet synergique. We also know that synergistins are antibiotics, isolated from culture media of various strains of Streptomyces, consisting of the combination of two types of factors (A and B) belonging to the group of
Streptogramins and acting in synergy. Factors A have a structure close to that of macrolides and factors B are cyclic heptapeptides. Each of the factors, taken in isolation, has a bacteriostatic activity, but the association A + B has a bactericidal activity characterizing a synergistic effect.
On a maintenant découvert que les antibiotiques de la classe des synergistines ont une activité bactériostatique et/ou bactéricide importante vis-à-vis de P.acnes, y compris sur les souches résistantes aux autres antibiotiques. Cette découverte est d'autant plus surprenante que l'on considérait jusqu a présent que les synergistines n'étaient pas utilisables dans le traitement de l'acné. C'est ainsi que dans le cas de la pommade
Staphylomycine, marque déposée pour une synergistine du type Virginiamycine, le fabricant indique que l'utilisation dans le traitement de l'acné est exclue ; voir Dictionnaire Vidal (DVP, Paris, France) édition 1985.It has now been discovered that antibiotics of the synergistin class have significant bacteriostatic and / or bactericidal activity with respect to P.acnes, including on strains resistant to other antibiotics. This discovery is all the more surprising since it was considered until now that synergistins were not usable in the treatment of acne. This is how in the case of the ointment
Staphylomycin, registered trademark for a synergistin of the Virginiamycin type, the manufacturer indicates that the use in the treatment of acne is excluded; see Vidal Dictionary (DVP, Paris, France) 1985 edition.
La présente invention a donc pour objet l'utilisation des antibiotiques de la classe des synergistines dans le traitement de l'acné. The present invention therefore relates to the use of antibiotics from the synergistin class in the treatment of acne.
Dans la présente demande, l'expression "synergistine" ou "antibiotique de la classe des synergistines" désignera un mélange d'au mdins une streptogramine A et d'au moins une streptogramine B. In the present application, the expression "synergistin" or "antibiotic of the synergistin class" will denote a mixture of at least one streptogramin A and at least one streptogramin B.
Autrement dit, l'invention a pour objet l'utilisation, dans le traitement de l'acné, de l'association d'au moins une streptogramine A et d'au moins une streptogramine B. In other words, the subject of the invention is the use, in the treatment of acne, of the combination of at least one streptogramin A and at least one streptogramin B.
Parmi les streptogramines A, on peut citer en particulier la virginiamycine M1, la mikamycine A, la pristinamycine II A ou II B, et la vernamycine A. Parmi les streptogramines B, on peut citer la virginiamycine S, la mikamycine B, les pristinamycines I A, I B, I C, et les vernamycines
B alpha, B bêta, et B gamma.Among the streptogramins A, mention may in particular be made of virginiamycin M1, mikamycin A, pristinamycin II A or II B, and vernamycin A. Among streptogramins B, mention may be made of virginiamycin S, mikamycin B, pristinamycins IA , IB, IC, and vernamycins
B alpha, B beta, and B gamma.
On peut bien entendu utiliser les antibiotiques de dénomination commune Virginiamycine (ou Staphylomycine), Pristinamycine, Streptogramine ou
Mikamycine, qui sont constitués de mélanges de streptogramines A et B.It is of course possible to use the antibiotics of common name Virginiamycin (or Staphylomycin), Pristinamycin, Streptogramin or
Mikamycin, which consist of mixtures of streptogramins A and B.
La virginiamycine peut être préparée selon le procédé décrit par
Somer et al., Antibiotics & Chemotherapy, 5, 632 (1955). Elle est constituée principalement d'un mélange de virginiamycine M1 et de virginiamycine S. La séparation des virginiamycines M1 et S et la caractérisation de ces deux constituants sont décrits par exemple par Vanderhaeghe et al., Antiobiotics & BR<
Chemotherapy, 7, 606 (1957) ; et Vanderhaeghe et al., J. Am. Chem. Soc., 82, 4414 (1960).Virginiamycin can be prepared according to the process described by
Somer et al., Antibiotics & Chemotherapy, 5, 632 (1955). It mainly consists of a mixture of virginiamycin M1 and virginiamycin S. The separation of virginiamycins M1 and S and the characterization of these two constituents are described for example by Vanderhaeghe et al., Antiobiotics & BR <
Chemotherapy, 7, 606 (1957); and Vanderhaeghe et al., J. Am. Chem. Soc., 82, 4414 (1960).
La mikamycine peut être préparée selon le procédé du brevet français 1.349.946. Mikamycin can be prepared according to the method of French patent 1,349,946.
L'isolement et la caractérisation de la mikamycine A sont décrits par exemple par Okabe, J. Antibiotics (Japan) Ser. A, 12, 89 (1959). The isolation and characterization of mikamycin A are described for example by Okabe, J. Antibiotics (Japan) Ser. A, 12, 89 (1959).
L'isolement, les propriétés et la structure de la mikamycine B sont décrits par exemple par Watanabe et al., J. Antibiotics (Japan) Ser.A, 12, 112 (1959) ; 13, 57 (1960) ; 13, 291-293 (1960) ; 14, 14 (1961).The isolation, properties and structure of mikamycin B are described, for example, by Watanabe et al., J. Antibiotics (Japan) Ser.A, 12, 112 (1959); 13, 57 (1960); 13, 291-293 (1960); 14, 14 (1961).
La mikamycine A est identique à la virginiamycine M1. Mikamycin A is identical to virginiamycin M1.
La pristinamycine peut être préparée selon le procédé du brevet français 1.301.857. Pristinamycin can be prepared according to the method of French patent 1,301,857.
La pristinamycine comprend d'une part les pristinamycines I A, I B et I C, et d'autre part les pristinamycines II A et II B. La séparation, la structure et la nomenclature des pristinamycines sont décrites notamment par
Preud'homme et al., Bull. Soc. Chim. France, 585 (1968) et Crooy et al.,
J.Antibiot. 25, 371 (1972).Pristinamycin comprises on the one hand pristinamycins IA, IB and IC, and on the other hand pristinamycins II A and II B. The separation, structure and nomenclature of pristinamycins are described in particular by
Preud'homme et al., Bull. Soc. Chim. France, 585 (1968) and Crooy et al.,
J. Antibiot. 25, 371 (1972).
La pristinamycine I A est identique à la mikamycine B. Pristinamycin I A is identical to mikamycin B.
La pristinamycine II A est identique à la virginiamycine M1. Pristinamycin II A is identical to virginiamycin M1.
La pristinamycine II B est la 2 6, 26, 27-dihydrovirginiamycine M1. Pristinamycin II B is 2 6, 26, 27-dihydrovirginiamycin M1.
Les vernamycines A et B peuvent être préparées selon le procédé du brevet US 2.990.325. La structure de ces produits est décrite par Bodanszki et al., Antimicrobial Agent & Chemoterapy, 360 (1963). Les vernamycines B comprennent la vernamycine B alpha (identique à la mikamycine B), la vernamycine B bêta et la vernamycine B gamma. Vernamycins A and B can be prepared according to the method of US Patent 2,990,325. The structure of these products is described by Bodanszki et al., Antimicrobial Agent & Chemoterapy, 360 (1963). Vernamycins B include vernamycin B alpha (identical to mikamycin B), vernamycin B beta and vernamycin B gamma.
Les vernamycines B alpha, B bêta et B gamma sont identiques respectivement aux pristinamycines I A, I B, et I C. Vernamycins B alpha, B beta and B gamma are identical respectively to pristinamycins I A, I B, and I C.
La streptogramine (mélange des facteurs A et B) peut être préparée selon le procédé du brevet britannique 776.035. Streptogramin (mixture of factors A and B) can be prepared according to the method of British patent 776,035.
Les synergistines sont utilisées dans le traitement de l'acné sous la forme de compositions administrables par voies topique, orale ou rectale. Synergistins are used in the treatment of acne in the form of compositions which can be administered topically, orally or rectally.
La voie topique est la voie d'administration préférée. Les compositions pharmaceutiques pour la voie topique se présentent par exemple sous la forme d'onguents, de teintures, de vernis, de pommades, de poudres, de tampons imbibés, de sprays ou de suspensions. Ces formes pharmaceutiques sont préparées selon les procédés usuels.The topical route is the preferred route of administration. The pharmaceutical compositions for the topical route are, for example, in the form of ointments, tinctures, varnishes, ointments, powders, soaked pads, sprays or suspensions. These pharmaceutical forms are prepared according to the usual methods.
Pour l'administration par voie topique, ces compositions contiennent généralement, dans un excipient ou véhicule approprié, 0,5 à 10% en poids de synergistine. Pour la voie orale ou rectale, elles contiennent 0,0005 à 95% en poids de synergistine et en particulier 85% pour la voie orale. Dans le cas de pansements préparés (tissus imprégnés, tampons imbibés), la concentration en synergistine est généralement de 0,5 à 2% en poids. For topical administration, these compositions generally contain, in an appropriate excipient or vehicle, 0.5 to 10% by weight of synergistin. For the oral or rectal route, they contain 0.0005 to 95% by weight of synergistin and in particular 85% for the oral route. In the case of prepared dressings (impregnated tissue, soaked tampons), the concentration of synergistin is generally 0.5 to 2% by weight.
Les proportions respectives des facteurs A et B peuvent varier de 10 : 90 à 90 : 10 en poids. The respective proportions of factors A and B can vary from 10: 90 to 90: 10 by weight.
Ces compositions pharmaceutiques peuvent contenir, outre des supports, excipients ou véhicules usuels, des additifs tels que
- un agent kératolytique comme l'acide salicylique, le peroxyde de benzoyle ou la trétinolne ; dans le cas du peroxyde de benzoyle, l'association pourra être faite au moment de l'utilisation ;
- un agent anti-fongique tel que les anti-fongiques imidazolés (éconazole, miconazole), les anti-fongiques allylaminés, les anti-fongiques triazolés, la grizéfuline, le sulfure de sélénium, la cyclopyroxolamine, etc...These pharmaceutical compositions can contain, in addition to the usual carriers, excipients or vehicles, additives such as
- a keratolytic agent such as salicylic acid, benzoyl peroxide or tretinoline; in the case of benzoyl peroxide, the association can be made at the time of use;
- an anti-fungal agent such as imidazole anti-fungals (econazole, miconazole), allylaminated anti-fungals, triazole anti-fungals, grizefuline, selenium sulfide, cyclopyroxolamine, etc ...
- un agent anti-séborrhéique local comme la progestérone, la
S-carboxyméthyl cystéine, la S-benzyl cystéamine et ses dérivés, les anti-androgènes locaux connus
- et dans le cas d'une composition pour la voie orale, un agent anti-androgène oral, tel que l'acétate de cyprotérone.- a local anti-seborrheic agent such as progesterone,
S-carboxymethyl cysteine, S-benzyl cysteamine and its derivatives, known local antiandrogens
- And in the case of a composition for the oral route, an oral anti-androgenic agent, such as cyproterone acetate.
- d'autres agents bactériens tels que par exemple la tioxolone ;
- un agent anti-inflammatoire non stéroldien, ou l'acétate de zinc.- other bacterial agents such as, for example, tioxolone;
- a non-steroidal anti-inflammatory agent, or zinc acetate.
Les compositions utilisables par voie locale peuvent encore contenir un agent favorisant la pénétration transcutanée comme la méthyl pyrrolidone ou le Laureth-4 (marque commerciale pour un acide laurique polyoxyéthyléné à 4 moles d'oxyde d'éthyléne). The compositions which can be used by the local route may also contain an agent promoting transcutaneous penetration such as methyl pyrrolidone or Laureth-4 (trademark for a polyoxyethylenated lauric acid containing 4 moles of ethylene oxide).
Les compositions pharmaceutiques utilisées selon l'invention peuvent également contenir des agents conservateurs, des agents stabilisants, des agents régulateurs de pH, des agents régulateurs de la pression osmotique, des agents émulsionnants, des antioxydants, des filtres UV-A et UV-B, etc... The pharmaceutical compositions used according to the invention can also contain preserving agents, stabilizing agents, pH regulating agents, agents regulating the osmotic pressure, emulsifying agents, antioxidants, UV-A and UV-B filters, etc ...
Ces compositions sont utilisées de façon à administrer localement 0,01g à O,lg par jour d'ingrédient actif (synergistine) et à administrer 1 à 4g par jour d'ingrédient actif par voie orale. Le traitement est appliqué jusqu'à la guérison. Le traitement est généralement bien toléré. On a toutefois signalé quelques effets secondaires après administration par voie orale (nausées, pesanteurs gastriques), et quelques cas de sensibilisation lors d'applications répétées de préparations à usage local. These compositions are used so as to locally administer 0.01 g to 0.1 g per day of active ingredient (synergistin) and to administer 1 to 4 g per day of active ingredient by oral route. The treatment is applied until healing. Treatment is generally well tolerated. However, some side effects have been reported after oral administration (nausea, gastric heaviness), and a few cases of sensitization during repeated applications of preparations for local use.
L'invention a également pour objet l'utilisation d'une synergistine (telle que définie précédemment) comme ingrédient actif dans la préparation de compositions pharmaceutiques anti-acnéSques. Ces compositions pharmaceutiques sont utilisées dans le traitement des troubles acnéiques tels que les acnés vulgaires polymorphes, les acnés post-médicamenteuses, les acnés professionnelles, les acnés cosmétiques, les acnés séniles et les acnés solaires. A subject of the invention is also the use of a synergistin (as defined above) as an active ingredient in the preparation of anti-acne pharmaceutical compositions. These pharmaceutical compositions are used in the treatment of acne disorders such as polymorphic acne, post-drug acne, professional acne, cosmetic acne, senile acne and solar acne.
Les synergistines peuvent également être utilisées, pour améliorer l'apparence de la peau, dans des compositions hygiéniques ou cosmétiques pour l'hygiène et les soins du visage et du dos, en particulier chez les sujets atteints de troubles acnéiques légers. Synergistins can also be used, to improve the appearance of the skin, in hygienic or cosmetic compositions for hygiene and care of the face and back, in particular in subjects suffering from mild acne disorders.
La présente invention a donc également pour objet des compositions cosmétiques contenant, dans un support ou véhicule cosmétique approprié, une synergistine telle que définie précédemment. The present invention therefore also relates to cosmetic compositions containing, in a suitable cosmetic carrier or vehicle, a synergistin as defined above.
Dans les compositions cosmétiques, la synergistine est présente à des concentrations pouvant varier entre 0,0005 et 1% en poids. In cosmetic compositions, synergistin is present in concentrations which can vary between 0.0005 and 1% by weight.
Les supports ou véhicules sont notamment ceux qui permettent de présenter la composition sous la forme de lotions (moussantes ou non), de gels, de savons, de pains dermatologiques, de crèmes, d'émulsions ou de laits pour le visage et le corps. Ces compositions cosmétiques sont préparées et appliquées selon les méthodes usuelles. The supports or vehicles are in particular those which make it possible to present the composition in the form of lotions (foaming or not), gels, soaps, dermatological breads, creams, emulsions or milks for the face and the body. These cosmetic compositions are prepared and applied according to the usual methods.
L'invention a également pour objet l'utilisation comme agent hygiénique ou cosmétique destiné à améliorer l'aspect des peaux acnéiques, d'une synergistine telle que définie ci-dessus. A subject of the invention is also the use as a hygienic or cosmetic agent intended for improving the appearance of acne-prone skin, of a synergistin as defined above.
Les exemples suivants illustrent l'invention sans toutefois la limiter. The following examples illustrate the invention without, however, limiting it.
EXEMPLE 1 : Lotion
On a préparé une lotion contenant
Mikamycine A 2 g
Mikamycine B 2 g
alcool isopropylique 85 g
eau 10 g
propylène glycol 5 g
Cette lotion est appliquée 1 à 2 fois par jour sur les lésions.EXAMPLE 1: Lotion
We prepared a lotion containing
Mikamycin A 2 g
Mikamycin B 2 g
isopropyl alcohol 85 g
water 10 g
propylene glycol 5 g
This lotion is applied 1 to 2 times a day on the lesions.
EXEMPLE 2 : Crème
On a préparé une crème fluide contenant
Vernamycine A 2 g
Vernamycine B alpha 2 g
Tween 60 5 g
Span 60 2 g
alcool éthylique 10 g
Miglyol 812 10 g
eau qsp 100 g
Cette crème est appliquée 1 à 2 fois par jour sur les lésions.EXAMPLE 2: Cream
We prepared a fluid cream containing
Vernamycin A 2 g
Vernamycin B alpha 2 g
Tween 60 5 g
Span 60 2 g
ethyl alcohol 10 g
Miglyol 812 10 g
water qs 100 g
This cream is applied 1 to 2 times a day on the lesions.
Tween 60 est une marque commerciale pour un monostéarate de sorbitan oxyéthyléné à 20 moles d'oxyde d'éthylène. Tween 60 is a trademark for an oxyethylenated sorbitan monostearate containing 20 moles of ethylene oxide.
Span 60 est une marque commerciale pour un monostéarate de sorbitan. Span 60 is a trademark for a sorbitan monostearate.
Miglyol 812 est une marque commerciale pour un mélange de triglycérides d'acides gras saturés en C8-C 12. Miglyol 812 is a trademark for a mixture of C8-C 12 saturated fatty acid triglycerides.
EXEMPLE 3 : Gel
On a préparé un gel pour la peau contenant
Virginiamycine M1 2 g
Mikamycine B 2 g
éthanol 20 g
Klucel HF 2 g
Eau qsp i0O g
Ce gel est appliqué 1 à 2 fois par jour sur les lésions.EXAMPLE 3 Gel
We prepared a skin gel containing
Virginiamycin M1 2 g
Mikamycin B 2 g
ethanol 20 g
Klucel HF 2 g
Water qs i0O g
This gel is applied 1 to 2 times a day on the lesions.
Klucel HF est une marque commerciale pour une hydroxypropylcellulose. Klucel HF is a trademark for a hydroxypropylcellulose.
EXEMPLE 4 : Gelule pour la voie orale
On a préparé des gelules ayant la composition suivante
Pristinamycine II 1 g
Pristinamycine I 1 g
amidon de mais 0.060 g
lactose 0.300 g
La poudre obtenue est conditionnée dans une gelule dont la paroi est
composée de gélatine, de TiO2 et d'un conservateur.EXAMPLE 4 Oral capsule
Capsules having the following composition were prepared
Pristinamycin II 1 g
Pristinamycin I 1 g
corn starch 0.060 g
lactose 0.300 g
The powder obtained is packaged in a gelule, the wall of which is
composed of gelatin, TiO2 and a preservative.
Cette composition est administrée 1 à 3 fois par jour au moment des repas. This composition is administered 1 to 3 times a day with meals.
EXEMPLE 5 : Lait de toilette
On a préparé un lait de toilette pour l'hygiène du dos, du thorax et du visage contenant
Virginiamycine M1 0,25g
Virginiamycine S 0,25g
Alcool cétostéarylique 3,10g
Alcool cétostéarylique
oxyéthyléné à 33 moles d'oxyde
d'éthylène 0,090g
Monostéarate de glycérol 1,00g
Huile d'amandes douces 6,00g
Huile de silicone 1,00g
Glycérine 15,00g
Eau qsp 100,00g
Ce lait de toilette est appliqué deux fois par jour. EXAMPLE 5: Cleansing milk
We have prepared a toilet milk for back, chest and face hygiene containing
Virginiamycin M1 0.25g
Virginiamycin S 0.25g
Cetostearyl alcohol 3.10g
Cetostearyl alcohol
oxyethylenated to 33 moles of oxide
ethylene 0.090g
Glycerol monostearate 1.00g
Sweet almond oil 6.00g
Silicone oil 1.00g
Glycerin 15.00g
Water qs 100.00g
This toilet milk is applied twice a day.
TESTS IN VITRO
On a étudié la concentration minimale inhibitrice (CMI) de diverses souches de P.acnes comprenant des souches de référence et des isolats récents collectés par le Centre National de Référence Anaérobie (Institut PASTEUR).IN VITRO TESTS
The minimum inhibitory concentration (MIC) of various strains of P. acnes was studied, including reference strains and recent isolates collected by the National Anaerobic Reference Center (PASTEUR Institute).
Des souches hébergeant des caractères de résistance connus aux MLS (Macrolides-Lyncosamines-Streptogramines) ont été inclues (provenant du Centre
National de Référence Anaérobie ou du Centre National de Référence sur la
Résistance - Institut PASTEUR).Strains harboring known resistance characters to MLS (Macrolides-Lyncosamines-Streptogramines) were included (from the Center
National Anaerobic Reference Center or the National Reference Center for
Resistance - PASTEUR Institute).
Les bottes, comprenant un milieu gélosé, sont coulées la veille de l'expérience puis mises en anaérobiose. L'incubation s'effectue à 370C en chambre anaérobie. The boots, comprising an agar medium, are poured the day before the experiment and then put under anaerobic conditions. Incubation takes place at 370C in an anaerobic chamber.
Le milieu de culture utilisé était le milieu viande levure (VL) additionné de 1% de sang de mouton. The culture medium used was the yeast meat (VL) medium supplemented with 1% sheep blood.
La lecture s'effectue à 18h et à 48h, avec 2 bottes par essai. Reading takes place at 6 p.m. and 48 a.m., with 2 boots per test.
Les essais ont été effectués avec la pristinamycine IA (P1) de Rhône
Poulenc, la pristinamycine IIB (P2) de Rhône-Poulenc, et l'antibiotique commercial Pristinamycine (P) de Rhône-oulenc qui est un mélange des facteurs
P1 et P2, ainsi qu'avec la clindamycine (Cl) de Upjohn et l'érythromycine (Em) de Roussel-Uclaf.The tests were carried out with pristinamycin IA (P1) from Rhône
Poulenc, pristinamycin IIB (P2) from Rhône-Poulenc, and the commercial antibiotic Pristinamycin (P) from Rhône-oulenc which is a mixture of the factors
P1 and P2, as well as with clindamycin (Cl) from Upjohn and erythromycin (Em) from Roussel-Uclaf.
Les résultats (C.M.I. en pglml) sont résumés dans le Tableau I suivant
TABLEAU I
Souches Cl Em Pl P2 P
P.a 85-176 < 0.06 < 0.06 8 0.5 < 0.06
P.a 85-219 < 0.06 < 0.06 8 0.5 < 0.06
P.a 85-291 < 0.06 < 0.06 8 0.5 < 0.06
P.a 85-307 < 0.06 < 0.06 16 0.5 < 0.06
P.a 85-315 < 0.06 < 0.06 8 0.5 < 0.06
P.a 85-316 < 0.06 < 0.06 8 0.5 < 0.06
P.a 85-317 < 0.06 < 0.06 16 0.5 0.125
P.a 85-318 < 0.06 < 0.06 8 0.5 < 0.06
P.a 85-319 0.5 0.125 8 32 0.25
P.a 85-411 0.25 < 0.06 8 0.5 (0.06
P.a 85-484 0.5 < 0.06 8 32 0.5
P.a 85-600/2 < 0.06 < 0.06 8 0.5 < 0.06
P.a 85-640 < 0.06 < 0.06 8 0.5 < 0.06
P.a 85-650 0.06 0.06 8 16 < 0.06
P.a 85-663 0.125 < 0.06 8 < 0.06 < 0.06
P.a 85-673 < 0.06 < 0.06 32 0.5 < 0.06
P.a 85-725 < 0.06 - 4 > 128 32 2
P.a 85-729 > 128 > 128 > 128 128 16
P.a 85-730 < 0.06 0.06 16 1 < 0.06
P.a 84-138 < 0.06 0.06 16 0.5 < 0.06
P.a 84-404 < 0.06 0.06 16 0.5 < 0.06
P.a 84-416 < 0.06 < 0.06 8 0--.5 < 0.06
P.a 84-425 < 0.06 < 0.06 8 0.5 < 0.06
P.a 5107 < 0.06 4 > 128 4 1
Ces résultats montrent
1) Que sur les souches sensibles à l'érythromycine et à la clindamycine, l'association des deux synergistines est toujours au moins aussi efficace que l'érythromycine et la clindamycine. En général, la CMI des synergistines vis-à-vis des souches sensibles est inférieure à 0,06pg/ml (8 premières souches du tableau, 12e, 13e et 19e à 24e). The results (CMI in pglml) are summarized in the following Table I
TABLE I
Cl Em Pl P2 P strains
Pa 85-176 <0.06 <0.06 8 0.5 <0.06
Pa 85-219 <0.06 <0.06 8 0.5 <0.06
Pa 85-291 <0.06 <0.06 8 0.5 <0.06
Pa 85-307 <0.06 <0.06 16 0.5 <0.06
Pa 85-315 <0.06 <0.06 8 0.5 <0.06
Pa 85-316 <0.06 <0.06 8 0.5 <0.06
Pa 85-317 <0.06 <0.06 16 0.5 0.125
Pa 85-318 <0.06 <0.06 8 0.5 <0.06
Pa 85-319 0.5 0.125 8 32 0.25
Pa 85-411 0.25 <0.06 8 0.5 (0.06
Pa 85-484 0.5 <0.06 8 32 0.5
Pa 85-600 / 2 <0.06 <0.06 8 0.5 <0.06
Pa 85-640 <0.06 <0.06 8 0.5 <0.06
Pa 85-650 0.06 0.06 8 16 <0.06
Pa 85-663 0.125 <0.06 8 <0.06 <0.06
Pa 85-673 <0.06 <0.06 32 0.5 <0.06
Pa 85-725 <0.06 - 4> 128 32 2
Pa 85-729>128>128> 128 128 16
Pa 85-730 <0.06 0.06 16 1 <0.06
Pa 84-138 <0.06 0.06 16 0.5 <0.06
Pa 84-404 <0.06 0.06 16 0.5 <0.06
Pa 84-416 <0.06 <0.06 8 0 -. 5 <0.06
Pa 84-425 <0.06 <0.06 8 0.5 <0.06
Pa 5107 <0.06 4> 128 4 1
These results show
1) That on strains sensitive to erythromycin and clindamycin, the combination of the two synergistins is always at least as effective as erythromycin and clindamycin. In general, the MIC of synergistins with respect to sensitive strains is less than 0.06 pg / ml (first 8 strains in the table, 12th, 13th and 19th to 24th).
2) Dans tous les cas (souches sensibles et souches résistantes), la synergie A+B est observée. 2) In all cases (sensitive and resistant strains), synergy A + B is observed.
3) En ce qui concerne les souches résistantes
a) 2 souches résistantes à ltérythromycine (CMI 4pg/ml) sont sensibles à l'association pristinamycine'(IA + IIB).3) Regarding resistant strains
a) 2 strains resistant to lerythromycin (MIC 4pg / ml) are sensitive to the association pristinamycin '(IA + IIB).
b) Une souche (85.729) très résistante à la clindamycine et à l'érythromycine (CMI 128 pg/ml) n'est que modérément résistante à la pristinamycine (IA + IIB) (CMI 16pg/ml). b) One strain (85.729) very resistant to clindamycin and to erythromycin (MIC 128 pg / ml) is only moderately resistant to pristinamycin (IA + IIB) (MIC 16pg / ml).
c) Une souche (85.725) résistante à l'érythromycine et modérément résistante à la pristinamycine (IA + IIB) (CMI 2pg/ml) reste sensible à la clindamycine. c) A strain (85.725) resistant to erythromycin and moderately resistant to pristinamycin (IA + IIB) (MIC 2pg / ml) remains sensitive to clindamycin.
En conclusion, l'association de pristinamycine (lA + IIB) se révèle aussi efficace que l'érythromycine ou la clindamycine sur les souches sensibles et plus efficace que l'érythromycine sur les souches résistantes à l'érythromycine. D'autre part, il ne semble pas y avoir de résistance croisée systématique clindamycine-pristinamycine. En effet, pour la souche 85.663, la pristinamycine est plus efficace que la clindamycine, alors que c'est l'inverse pour une autre souche (85.725). In conclusion, the combination of pristinamycin (1A + IIB) appears to be as effective as erythromycin or clindamycin on sensitive strains and more effective than erythromycin on strains resistant to erythromycin. On the other hand, there does not seem to be any systematic cross-resistance between clindamycin and pristinamycin. Indeed, for the strain 85.663, pristinamycin is more effective than clindamycin, while it is the opposite for another strain (85.725).
Au total, cette étude montre la supériorité de la Pristinamycine sur l'Erythromycine. Elle montre une activité similaire à celle de la
Clindamycine. Toutefois, l'absence de résistance croisée avec cet antibiotique montre que les cas de résistance à la Clindamycine pourront être traités par la Pristinamycine (et inversement). In total, this study shows the superiority of Pristinamycin over Erythromycin. It shows an activity similar to that of the
Clindamycin. However, the absence of cross-resistance with this antibiotic shows that cases of resistance to Clindamycin can be treated with Pristinamycin (and vice versa).
Claims (13)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8710998A FR2619008B1 (en) | 1987-08-03 | 1987-08-03 | USE OF SYNERGISTINS IN ANTI-ACNEIC PHARMACEUTICAL OR COSMETIC COMPOSITIONS |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8710998A FR2619008B1 (en) | 1987-08-03 | 1987-08-03 | USE OF SYNERGISTINS IN ANTI-ACNEIC PHARMACEUTICAL OR COSMETIC COMPOSITIONS |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2619008A1 true FR2619008A1 (en) | 1989-02-10 |
| FR2619008B1 FR2619008B1 (en) | 1990-06-29 |
Family
ID=9353826
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8710998A Expired - Lifetime FR2619008B1 (en) | 1987-08-03 | 1987-08-03 | USE OF SYNERGISTINS IN ANTI-ACNEIC PHARMACEUTICAL OR COSMETIC COMPOSITIONS |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2619008B1 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2701709A1 (en) * | 1993-02-17 | 1994-08-26 | Rhone Poulenc Rorer Sa | Purified form of streptogramins, its preparation and pharmaceutical compositions containing it. |
| EP0614910A1 (en) * | 1993-02-17 | 1994-09-14 | Aventis Pharma S.A. | Streptogramines in purified form, their preparation and pharmaceutical compositions comprising them |
| AP520A (en) * | 1993-02-17 | 1996-08-26 | Rhone Poulenc Rorer Sa | Purified form of streptogramins, its preparation and pharmaceutical compositions containing it. |
| US6384014B1 (en) | 1994-08-02 | 2002-05-07 | Aventis Pharma S.A. | Purified form of streptogramines, preparation of same and pharmaceutical compositions containing them |
| WO2006073151A1 (en) * | 2005-01-05 | 2006-07-13 | Astellas Pharma Inc. | Novel fermentation product |
-
1987
- 1987-08-03 FR FR8710998A patent/FR2619008B1/en not_active Expired - Lifetime
Non-Patent Citations (2)
| Title |
|---|
| DICTIONNAIRE VIDAL, édition 62, 1986, page 1418, O.V.P., Paris, FR * |
| DICTIONNAIRE VIDAL, édition 62, 1986, pages 1418-1419, O.V.P., Paris, FR * |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2701709A1 (en) * | 1993-02-17 | 1994-08-26 | Rhone Poulenc Rorer Sa | Purified form of streptogramins, its preparation and pharmaceutical compositions containing it. |
| EP0614910A1 (en) * | 1993-02-17 | 1994-09-14 | Aventis Pharma S.A. | Streptogramines in purified form, their preparation and pharmaceutical compositions comprising them |
| BE1006554A3 (en) * | 1993-02-17 | 1994-10-11 | Rhone Poulenc Rorer Sa | PURIFIED FORM streptogramins, PREPARATION AND PHARMACEUTICAL COMPOSITION CONTAINING SAME. |
| WO1996005219A1 (en) * | 1993-02-17 | 1996-02-22 | Rhone-Poulenc Rorer S.A. | Purified form of streptogramines, preparation thereof and pharmaceutical compositions containing it |
| ES2081763A1 (en) * | 1993-02-17 | 1996-03-01 | Rhone Poulenc Rorer Sa | Streptogramines in purified form, their preparation and pharmaceutical compositions comprising them. |
| AP520A (en) * | 1993-02-17 | 1996-08-26 | Rhone Poulenc Rorer Sa | Purified form of streptogramins, its preparation and pharmaceutical compositions containing it. |
| US5637565A (en) * | 1993-02-17 | 1997-06-10 | Rhone-Poulenc Rorer S.A. | Purified form of streptogramins, its preparation and pharmaceutical compositions containing it |
| AU678785B2 (en) * | 1993-02-17 | 1997-06-12 | Rhone-Poulenc Rorer S.A. | Purified form of streptogramins, its preparation and pharmaceutical compositions containing it |
| GB2275269B (en) * | 1993-02-17 | 1997-07-09 | Rhone Poulenc Rorer Sa | Purified form of streptogramins,its preparation and pharmaceutical compositions containing it |
| US5726151A (en) * | 1993-02-17 | 1998-03-10 | Rhone-Poulenc Rorer S.A. | Purified form of streptogramins, its preparation and pharmaceutical compositions containing it |
| AT406052B (en) * | 1993-02-17 | 2000-02-25 | Rhone Poulenc Rorer Sa | PURIFIED FORM OF STREPTOGRAMINS, THEIR PRODUCTION AND THE PHARMACEUTICAL MEASURES CONTAINING THEM |
| US6384014B1 (en) | 1994-08-02 | 2002-05-07 | Aventis Pharma S.A. | Purified form of streptogramines, preparation of same and pharmaceutical compositions containing them |
| WO2006073151A1 (en) * | 2005-01-05 | 2006-07-13 | Astellas Pharma Inc. | Novel fermentation product |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2619008B1 (en) | 1990-06-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3969516A (en) | Composition and method for treatment of acne | |
| US4839159A (en) | Topical L-carnitine composition | |
| EP0747047B1 (en) | Combination of an antimicrobial compound (e.g. the lipoaminoacid N,n-octanoyl-glycine) and a monoalkylglycerol ether and its use as an antimicrobial agent | |
| JP3739803B2 (en) | Novel antimicrobial cosmetic composition | |
| JPH10509437A (en) | Deodorant, antimicrobial and preservative compositions and methods of using them | |
| AU2006205561A1 (en) | Methods and pharmaceutical compositions useful for treating psoriasis | |
| EP1283708B1 (en) | Use of biguanide derivatives for making a medicine having a wound healing effect | |
| EP0862910A2 (en) | Use of retinoids as skin pigmentation inducing agent | |
| EP0953345B1 (en) | Use of at least a hydroxystilbene as an agent for decreasing micro-organisms adhesion | |
| US20100184727A1 (en) | Treatment of excess sebum production | |
| WO2008059190A1 (en) | Treatment of excess sebum production | |
| BE897195A (en) | NEW METHYLSTRYRYLNAPHTALENE DERIVATIVE, ITS PREPARATION AND ITS APPLICATION AS A MEDICINAL PRODUCT | |
| FR2822380A1 (en) | Preventing adhesion of microbes to skin and mucosa, useful in cosmetics and for treating e.g. acne, using mixture of metal ions, hydrogencarbonate and o-diphenol | |
| EP0909557B1 (en) | Use of honey as an agent for decreasing micro-organisms adhesion | |
| FR2619008A1 (en) | Use of synergistins in pharmaceutical or cosmetic anti-acne compositions | |
| CA1289884C (en) | ANTI-INFLAMMATORY MEDICAMENT HAVING A SYNERGISTIC ACTIVITY AND COMPRISING A CORTICOSTEROID AND A .beta.-AGONIST | |
| WO2008102086A2 (en) | Use of compositions containing at least one lignane and/or neolignane for modulating testosterone levels | |
| US20050101632A1 (en) | Method for the treatment of inflammation | |
| WO2025090117A1 (en) | Compositions and methods for treatment of wounds and inflammatory skin conditions | |
| FR2558058A1 (en) | Metronidazole based dermatological compositions for external topical use, which are useful in the treatment of acne | |
| US20180289656A1 (en) | Compositions and methods to treat urinary tract infections | |
| WO2007107663A2 (en) | Use of (3s)-n-hydroxy-4-({4-[(4-hydroxy-2-butynyl)oxy]phenyl}sulfonyl)-2,2-dimethyl-3-thiomorpholine carboxamide or (s)-n-hydroxy-4-(4-but-2-ynyloxy-benzenesulfonyl) -2,2-dimethyl-thiomorpholine -3-carboxamide for treating inflammatory skin pathologies | |
| EP1096933B1 (en) | Use of an inhibitor of cytochrome p450 optionally combined with an antifungal agent for treating mycoses | |
| WO2019079089A2 (en) | Method to treat antimicrobial resistant candida | |
| FR2747308A1 (en) | Use of azadirachta indica, hydroxycitrate, ceramides and optionally vitamins or caffeine |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |