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CA2362757C - Effervescent pharmaceutical formulation containing metamizole - Google Patents

Effervescent pharmaceutical formulation containing metamizole Download PDF

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Publication number
CA2362757C
CA2362757C CA2362757A CA2362757A CA2362757C CA 2362757 C CA2362757 C CA 2362757C CA 2362757 A CA2362757 A CA 2362757A CA 2362757 A CA2362757 A CA 2362757A CA 2362757 C CA2362757 C CA 2362757C
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Prior art keywords
pharmaceutical composition
effervescent formulation
sodium
effervescent
tabl
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Expired - Fee Related
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CA2362757A
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CA2362757A1 (en
Inventor
Brigitte Freudensprung
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Hexal AG
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Hexal AG
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0002—Galenical forms characterised by the drug release technique; Application systems commanded by energy
    • A61K9/0007—Effervescent
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
    • A61K31/4152—1,2-Diazoles having oxo groups directly attached to the heterocyclic ring, e.g. antipyrine, phenylbutazone, sulfinpyrazone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]

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  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pain & Pain Management (AREA)
  • Organic Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Rheumatology (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

The invention relates to a stable pharmaceutical effervescent formulation with metamizol and/or its pharmaceutically acceptable salts as active ingredients, wherein the pH of the corresponding solution is acidic.

Description

i 0 . RUG . 2001 13 : 40 HE~RL~RG y+49~80~4.~908154 212-68'T1%-ltti I~ . 341 S
. 3i i 5 I
SENC ~Y.CPLY ,_-. ' 212 42155 g~texwasceat outzcal iosmtalati.oa aost arl~amisole The invention relates to a stable ei~fervescent phaxmaceutical formulation with metamxzole aad/dr its pharmaceutically acceptable ~alte as active ingred~.ents, the p~ o~ the resulting aoyution being aoidi,c.
Metamizole, N-methyl.-~N- (2, ~-dimethyl--~-oxn-1--phenyl -pyrasolin-4-y1)ami,nomethanee~ulfonic acid, is an. analgesic with antipyreti.e ef~ecta. The anal.g~eic effect arises through depression of central pain perception as a ree~ult of activation of neurons 3_n the pain-lz~hibiting syr~tem. The reduction ~,r~ elwrrated body temperature is mediated by the action on the hypothalamic head,-regulating center, result~.ng in iacrea,aed dissipation of heat via the periphexy_ After oral intake, the absorption of metaa~izele is~ preceded by hydrolys~,s to 4.-mrthylam3.x~ox~utipyrfno in the liv~cs.
4-Methylaminoautipyra.ne and the 4-aminoantipyrine produced therefrom ere Che phannacol.ogiaally ac:Live n~tabolZtes of rnetamzzole, whi~.e the other metabolites 4-acetylaminoanti.-pyrine (main metabolite ix~ the urine) and 4--tormylaminvanti-pyrine are regardc~~ as having vexy much 7,ese pharmacoXogiaal acti~rity or being inac~,ive. 7lfter oral administration of tablets availavble on the market to date, the pharmacologically active plasma concentration of methylaminoantipyxitZe is reached after 1.4 ~rc~u=s, and of 9-anti.noantipyrinc~ after 6 _'7 hour~.

11~.RUG.2001 13:40 HEXHL RG +49 8024_ 908154 212~(7t17~~fIU''. _. IVR.341 5.4115 ''I
SENT BY - Ct'Lx' , .. ~ . ~ _ . _ _ . ' 212 42~.~
' - a -It is desirable for a pharmacologically active plasma aoz~centration and thue~ a therapeutic effect to be reached as quickly as po~ssi.ble because metamizole is used to treat acute sever~ pain. The ~injeGtion dosage form which is fxequeritly used for this purpose requires care which can be prrnridad only by specialist medical staff beGauee, othertaiee, an inj ection rate which is too fast sad a dosage which ie tov high rer~ult in life~threatening Side effects, such as, for example, sudden circulatory failux'e or agranulocytosia. zrr addition, patient compliance vaith an injection is vary low.
Th~ obj eat of the invention f,s~ now to provide! a stable effervesce~nt formulatiozi with ece;tamizole and/or its pharmacsuticax~.y acceptable salts as active cox~ts, so that the pharntacologiaally effective plasma aoncsntration and thus the therapeutic effect can be reached teeter than w~.th carrvertional dosage fozma for oral admin3.stratfor~, but direct medical care during ~.ntake can be dispensed w~.th because theses is ao rie~k of life-thre4tening aide ef~ecte.
The stability of mete~mizole and i.ts pharmaaeuti.cally acceptable salts is pH-deperxdent. Metamiaole or ~.ts pharm$ceutioal7.y acceptabl~ qalts is stable its neutral and basic odium. In acidic medium, however, hydrolysis takes place ~rexy rapid7.y and ie indiaats~d by a ye7.lo~r coloration.
The exca.pienta normally used to produce effervescent tablets generate tin aci.d~.c modiurn in aqueous solution.
Tt has sow been found, auxpx~igingly, that despite a~ci ao~.dic pH of the eLF~rvescent formulation s~olutian the active . RUG. 2001 13: 40 hIEXRL faG +49 8024w908154 '~12-6B"J-'~'TTQ-WyR. 341 S. 515 I i ~ iv u- a a , v-' . ' 212 A212~5 ingredient metamizoie and/or its pharmaceutically acceptable salts is not subaeet to hydrolysis, that is to say is stable.
without addition of special. stabil~,sing subetences, grad a therapeutiGa3,3.y effective plasma level is reached very quiek7.y. An additional adstantage eocopared with dosage forms for oral administration available on the market to date is that intake of the medicament ie made more pleasant for the patient by flavoring the effer<rascent io~lation.
The effervescent formulation of the invention tray contain metamizole and/or iCe phazmaceutiCa7.ly acceptable salts as act,iwe ~.r~gred~.ent~a . ~osaibZe and suitab~.e metamizole salts are, in particular, alkali metal salts such aa, for example, the potag~eium, sodium az~d lithium salts, especial~.y metami zole c~odiutn monohydr. aCe, and the at'imnonium salt .
Thde effervescent formulation of the invention can comprise an effectwn amount of 200-~, o00 ng, in particular of X04-600 mg, of raetamizole a~0.d/or ~.te~ pharmaceutically acceptable calls par dosage unit.
The preferred effervGSCent formulation of the invention comprises 50o tng of rnetamizole soda.um mozsohydrate peat dosage un'i t .
The effexveecent formu~,ation of the invention dissolved in water hao a pII of from 3 to 6 . 5 , in particular of from 4 to 6, pretexably of from 6.5-5, and the xerultiag selution is ~table and e7.ear fer at least ons hour_ rt ~.s posailile to use as source of aarbori dioxide is the effex~ra~cent fo~nulatioi~ of Che invention the oarbonate BY0~~.2001 13:41 HEAL A6~+49 A024, 908154 'Z' ~,2-B87~lTIU-~ NR.341 S.6i15 I I
' "' . ' ~i2 412255 -and/or bicarbonate of the alkali metals and/o~c alkaii~re earth metals, for exa~le sodium carbonat~ or sodium baearbonate, calcium ce~rboxiate or calcium bicarbonate and/or neelmn carbona~tc or rctagne~sium bicr~~rbonate, in con~unetion wilts at least one acid, for exampl~ citric acid, monosod~.um citrate, ascorbic ac3.d, gluconic acid, lactic acid, ma~.eic acid, and tartaric acid. tn the prefeaCred Pffervescent formu2stion of the invar~.tion, citric acid is used with a combination of sodiutra carbonate and sodium bicarbonate aw off8rvisoexl~.
mixture. In this case the retie by v~e~.ght of the acid (s) to the carbonat~ and/ax the bicarbonate can ~ batweer~ 0 . ~ acrd
2.4, in particular between 1.7. and 2.~.
An acceptable taste of the reault~.ng solution of the aCt~.ve ingredient ~:an las achieved by adding su~.txbl~ maalcing ' flavors such as flavorings, sugar, sucrose or sugar e~ubati,tutee . Sugar or e~ugar substitutes caay be pre~er~t in a~n, amount of up to about 50~ by weight. Masking flavors suitable for producing Che afferveecent formulation of the invention are artificial or natural ~eweeteners (0.a to ~~r by weight), preferably saccharin sodium, sodium cyclamate, sorbitol, aepartarte or mannitoi, or artificial or natural tla~ror3ng8, preferably ~,emon, banana, peppermint, caramel, wild fruit and rampberry flavor. The flavors arc preferably used in an amount of from 0.~ to 3% by wesght, In addition, water-ga~.ubla pharsnavaut~.Gal Lablet exexpients lrnown from the prior art are a~ad to produce the efferv~esCenc formulation of the inv~ent~.on, for example -" 10.RLJG.2001 13:41 HE~RL~RGr+49~8024__90A154 212-6S7W'/~/U-' NR.341 S.?il5lll~
~I'C BY ~ Ct'L.Y . , _ ' . ' 212 421?255 _ r~ _ tilJ.era and bindmrs imar~nitol), and lubricants (polyethylene glycole, Comprztol, L-1~uci.ne, mac,~naaiuen ate~arate, stearic acid) , As other pos~a~.ble tablet exeigsent9 it is poaa~ible to add where appropriate one ox more polysaeahaxides. Preferred pvlyaaccharides are cyclodextr~.ns. possible representatives are oc~ , ~3m Y-cyclodextrin and/or the~.r phartnaveutically acceptable derivatives, in particular ~-cyclodextria.
The efferrrescent formulation o~ the invention ma.y be in the =orm of a powder, tab~.ets or granules, which can be packed in sachots. The preferred efferv~scent formulation is irx the form of tablets .
The invention ~.~s illustrated in the table by the followilzg exampl~s without, hoareve'x~, thereby reatrictirtg the arcope of the invention.
1e 1:
rim n Metamizole eodiutri monohydxa~te 500 mg/tah~..

Citric acid 1 a30 mgjta~bl..

Bodium caxbon~te 650 mg/tabl.

Sodium hydrogen carbonate (bicarbonate) 95 mg/tabi.

Ascorbic acid ~W ag/tabl.

T,actoee X00 mg/tahl.

Saccharin sodium 5 mg/tabl.

P8G,6000 135 mg/tabl.

SCdluIrl Cy~"'Zattici4Et SO t~,/Cabl.

Flavor (lemot'a) 50 mg/tabl.

10.RUG.2001 13:41 HEXRL RG +49 8024 908154 212-88'x-2770-~ r~.341 5.8~15I~~t~
SENT BY : Gf LP - -. o- a a , ~ s... ,.. -, ' ~ 212 4212255 ~'he total v,~ight of a tablet ie 3 X90 mg .
Metamxzole ~od~.u~n moruahydrate and PEG 6000 are ground and screened, and the remaining ~.ngredisr~ts are admixed. The myxture xs aompreesed to 3 X90 mg tablote with a di~tcr of 20 mm. Disaalutiox~ results in a clear solution. ~.'he active ingredient is stable for one. hour. The ratio by weight of citric acid to carbonato/bicarbonate corresponds to about 7.
a s a . r.
Metamizolm sodium manvhydrate 500 ~g/tabl.
Citric acid Z 230 mg/tabl.
Sod~,um carbonate 650 rng/tabl.
Sodium hydrogen carbonate (bicarbonate) 75 mg/tabl.
Ascorbic acid 75 mg/tabl.
Laato~e moriohydrate &oo mg/tabl.
Saccharin. sodium 5 mg/tabl.
PBG 6000 155 mg/tabl.
Soda.um cyclamate 50 m~/tabl.
r~lavor ~ra8pber~y) 30 mg/tab7..
The total weight of a tablet is 3 ~~0 mg.
l~letamizole ~od~.vm monohydrate and PEG 6000 aze ground and screened, and the remaining ingredients are achnixed. ~'he mixture is compressed to 3 270 mg tabletA w~.th a diameter of 25 man using a rotary tableting machxr~e~. Dissolution z-esults in a c7.ear aoZut3on. The active ingredieac is atablrs for ors ~10.RUG.2001 13~41 HEXRL RG +49 8024 908154 21~-687-277Q-~ NR.341 S.9/l5lartu ~ c-~w w -~
' 212 4212255 . - 7 ..
hour. The ratio by weight of citx~.a acid to oarbonate/
bicarb~ate corraaponds to about 1.~.
~e 3:
~_ rt.
l~leetasnixeal.e sodium monohydrate 500 t~g/tab7..

Citrf c acid 1. 500 cag/tab~
.

6odium carbonate avt~hydroua 63 0 mg/tabl .

Sodium hydrogen carbonate tbicarbonate) 70 mg/tabl.

p~3 svoo i50 mg/Cabl.

Saccharin sodium 5 mg/tabl, Sodium cyclams~ta~ 30 mg/tabl.

Aaaorba.c acid 75 1~/tabl.

Lactome B30 mg/tabl.

Flavor (r~aepbar~r) 30 mg/tabZ
.

The total wreight of a tab~.et is 3 830 mpg.
Metami.~ole sodium moriohydxate, taa~ito7, and E8t3 so00 are ground and eQreensd, and the remaining ingrediexzte are admis;ed. The mi.xturs ~.s cot~apreaaed to 3 830 mg tab7.ets wi~Ch a diamet~r of as mm. The ratio by weight of citric acid to Gt~rbaszate/bicarbonate corresponds to about 2_14. 'fh~ pH of the Ao~.ution is x.50-4.s1-E'x~le ~ a Metami~sole sodium monohyrirate 500 ag/tabl.
Citric aoxd 750 mg/tabl.
Sodium carbonate anhydrous 900 m~g/tabl.
Sodium h~rdrogen carbonate (bicaxborr.ate) 50 mg/tabl.

10. RUG. 2001 ~ 13: 41 HEXfaL RG +49 8A24 908154 212-fi87-27?tH n~. 341 S.10~1 Is4' ~~
5~t'1' BY = CI'LP , ~ .~ ~, , ~.. - ... , ~ 212 42i~22S6 g _ Mawnitol 30 mg/tabl _ ~-Cyclode~ctrin l00 mg/tabl.

PBG 6000 96 ng/tabl_ Saccharin eoda.um 4 mg/tabl.

Sodium cy~alarnate 15 mg/tahl.

Ar~c:owbic: acid 75 mgjtsb~..

Lactose and PVg 80 mg/tabl.

Flavor tlemon) , SO mg/tabl.

The total weight of a tablet ie 2 650 mg, Metam:i.zole sodium monohydrate, mantZitol and PFG 6000 ere ground and screeruad, and the remaina.ng ingredients arc admixed. The Mixture ~.s comer~ssed to 2 63o mpg tablet$ w~.th a diaareter of 22 mm. The pH of the solution is about 5. Tha ratio by areight of citric acid to carbonate/bicaz~bOnate eorreaponds~ to 2tbout 0.79.
~.a S
Metamizole sodium cr~nohydrate 500 mg/tab7, .

Citric acid 1 200 mg/tabl.

6odium carlnonate aanhardroua 600 mg/tabl.

Sodium hydrogen carboz~ata (bicarbonates)27.8 mg/tabl.

P8G 6000 350 r~/tabl.

$aeaharin aodi.um 4 mg/tabl, .

Sodium cyclamate 40 ng/tabl.

MaleiC acid 300 rng/tabl.

zaCtose 1,20 mg/tsbl.

1~~x.2001 13:42 HE~HL~RG~+49FB024 908154 21'Z-sBW2771?~ NR.341 S. iliil5'" "' Sue' BY =Cft.,P w . - rr. ... .
' 212 A212255 Flavor (raspberry) 30 1~g/tdbl.
The total w~ight of a tablet is 3 262 mg.
Mctamizole eadium monohydrats~ and P8G 6000 are ground and screened, arrd the semainixsg a.ngrediar~te axe admixed. The mixtu~c~ f s cornpre~ssed to tablets . Dissolution r~ezxlts is a Blear solution. xhe a~ative ingredient ie ota.bl~ for one hour.
The ratio by weight of caCric acid tv oa~rbonat,e/bicarbonate carres~oads to about 1,67. The pH of the solution ie 4.56-4.72.
ly 6s Metamizole sodium rnonohydrate 800 mg/tabl.

citric acid 660 mg/tabl.

Sodium carbonate a~rshydrous 100 mg/tabl.

Sodium hydrogen carbonate (bicarbonate) 4a0 mg/tab3..

P8G 8000 25 thg/tabl.

Saccharin sodium 5 mg/tabJ..

Soc'9,~,utn cyc~.amate . 30 mg/tabl.

Ascorbic acid 75 mg/tabl..

~atose 120 ntg/tabl.

Flavor (wild berry/blaakberry) 50 mg/tab~..

The total weight of a tablet ~.s~ 1 985 tag.
~i~stamixole sodium monohydxate and RFC3 8000 are gxousui and eereened, and the remaining ~Lrtgrediente are admixed. The ritlXture i~ Cornp7CmsW 3d tc~ Cabl~t~ w~.Ch a diasl~ter o~ 20 mm.

~1~f1~ BY ~ Cf~..t' " '"'V.~"~l 1~:4~ FiE~AL~AG~+49~8024~908154 21$-687-Z77U-'w' w IVR.341 S.
l2iil5"' ,~.
' zsz aims - to -'The ratio bar areight of citric acid to caxbonate/bicarbotZate corresponds to about 1. a7.
axe ~ a r~tami~oZe sodium monohydrate 500 mg~tab~_ Ca~tric acid 666 mg/tabl , Sodium carbonate anhyd~g 633 mg~tabZ.

Sodium hydrogen earbonat~ (bicarbonate) 100 mg/tabl_ 3S0 r~g/tabl.

Saccharax~, sodium '~ mgltabl.

Sodium cyclamate 40 rng/tabl.

Maleic acid Z00 rng/tabl.

LaCtOae a~is mg/tabl.

Flavor (raspberry) 30 mg/tab7..
The total w~~,ght of a tablet is 2 799 mg.
Metami~ola sodium monohydrata and pEG 6000 are gro~d and screened, and the remaixsing ingredients arg admixed. The mixture is ~compreased to tablets. The rat~.o by weight of citric acid to carboxrate/bicaxbonata corresponds to about 0 . 91. The pH of thp 9ca.'I ut i can ~l s 5 . 73 -5 . 92 .

Claims (15)

claims
1. ~A pharmaceutical composition in the form of an effervescent formulation, characterized by metamizole and/or its pharmaceutically acceptable salts as active ingredients.
2. ~A pharmaceutical composition in the form of an effervescent formulation as claimed in claim 1, characterized by alkali metal salts and/or ammonium salts of metamizole as active ingredients.
3. ~A pharmaceutical composition in the form of an effervescent formulation as claimed in claim 1 or 2, characterized by metamizole sodium monohydrate as active ingredient.
4. ~A pharmaceutical composition in the form of an effervescent formulation as claimed in any of the preceding claims, characterized by a content of 200-1 000 mg, in particular 400-600 mg, of metamizole and/or its pharmaceutically acceptable salts per dosage unit.
5. ~A pharmaceutical composition in the form of an effervescent formulation as claimed in claim 4, characterized by a content of 500 mg of metamizole sodium monohydrate per dosage unit.
6. ~A pharmaceutical composition in the form of an effervescent formulation as claimed in any of the preceding claims, characterized by an effervescent mixture of at least one physiologically tolerated acid or its sodium salt and of a physiologically tolerated carbonate and/or bicarbonate in ratios of amounts such that the resulting solution has a pH
of from 3 to 6.5, in particular of from 4 to 6, preferably of from 4.5 to 5.
7. A pharmaceutical composition in the form of an effervescent formulation as claimed in claim 6, characterized by citric acid or its monosodium salt is combination with sodium carbonate and sodium bicarbonate as effervescent mixture.
8. ~A pharmaceutical composition in the form of an effervescent formulation as claimed in any of the preceding claims, characterized in that the ratio by weight of the acid(s) to the carbonate and/or bicarbonate in the effervescent mixture is between 0.7 and 2.4, in particular between 1.1 and 2.2.
9.~A pharmaceutical composition in the form of an effervescent formulation as claimed in any of the preceding claims. characterised by an optional content of a sweetener.
l0. ~A pharmaceutical composition in the form of an effervescent formulation as claimed an any of the preceding claims, characterised by an optional content of a flavor.
11. ~A pharmaceutical composition in the form of an effervescent formulation as claimed in any of the preceding claims in the form of powder, tablets or granules, which can be packed in sachets, in particular in the form of tablets.
l2. ~A pharmaceutical composition in the form of an effervescent formulation, characterized by metamizole sodium monohydrate, sodium carbonate/sodium bicarbonate, tableting excipients, where appropriate flavorings and/or sweeteners, the resulting solution having a pH of 3-6.5, in particular of 4.5-5.
13. ~A pharmaceutical composition as claimed in claim 1-12, characterized in that the effervescent formulation is stable.
14. A pharmaceutical composition as claimed in claim 1-12, characterized in that the solution of the effervescent formulation is stable and clear for at least one hour.
15. A pharmaceutical composition as claimed in claim 13 or 14, characterized in that the effervescent formulation comprises no additional stabilizing substances.
CA2362757A 1999-02-11 2000-02-10 Effervescent pharmaceutical formulation containing metamizole Expired - Fee Related CA2362757C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19905581.5 1999-02-11
DE19905581 1999-02-11
PCT/EP2000/001096 WO2000047189A1 (en) 1999-02-11 2000-02-10 Pharmaceutical effervescent formulation containing metamizol

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CA2362757C true CA2362757C (en) 2010-08-24

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CN103610656B (en) * 2013-12-05 2016-02-03 昆明振华制药厂有限公司 A kind of preparation method of analgin tablet
WO2015089614A1 (en) * 2013-12-16 2015-06-25 Hypermarcas S.A. Stable oral pharmaceutical composition
CN104434862A (en) * 2014-11-06 2015-03-25 石家庄正大鸿福牧业有限公司 Veterinary metamizole sodium effervescent tablets and preparation method thereof
BG112443A (en) 2017-01-19 2018-07-31 Adifarm Ead EFFERVENT COMPOSITION CONTAINING METAMIZOL SODIUM MONOHYDRATE AND METHOD FOR ITS PREPARATION
EP3928766A1 (en) 2020-06-26 2021-12-29 Usso Barnas Pharmaceutical composition and use thereof

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EP0971743B1 (en) * 1997-04-18 2006-07-12 Fritz Stanislaus Stabilized medicaments containing cysteinyl derivatives
DE19822036A1 (en) * 1998-05-15 1999-11-18 Bayer Ag Effervescent pharmaceutical composition with improved stability

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CA2362757A1 (en) 2000-08-17
BR0008442B1 (en) 2014-04-01
PT1150660E (en) 2004-06-30
DE50005076D1 (en) 2004-02-26
JP2002536401A (en) 2002-10-29
TR200102279T2 (en) 2001-11-21
BR0008442A (en) 2001-10-09
HUP0200336A3 (en) 2005-04-28
PL201844B1 (en) 2009-05-29
PL350413A1 (en) 2002-12-02
HUP0200336A2 (en) 2002-06-29
AU777234B2 (en) 2004-10-07
ES2215025T3 (en) 2004-10-01
EP1150660B1 (en) 2004-01-21
AU2804000A (en) 2000-08-29
WO2000047189A1 (en) 2000-08-17
EP1150660A1 (en) 2001-11-07
ATE258046T1 (en) 2004-02-15

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