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CN111166718A - Ornidazole injection and preparation process thereof - Google Patents

Ornidazole injection and preparation process thereof Download PDF

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Publication number
CN111166718A
CN111166718A CN201911161579.9A CN201911161579A CN111166718A CN 111166718 A CN111166718 A CN 111166718A CN 201911161579 A CN201911161579 A CN 201911161579A CN 111166718 A CN111166718 A CN 111166718A
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Prior art keywords
ornidazole
injection
acetic acid
sodium acetate
value
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CN201911161579.9A
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Chinese (zh)
Inventor
侯雯
张爱琴
高静
贾碧雪
杨君
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Nanjing Zhihe Medical Technology Co ltd
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Nanjing Zhihe Medical Technology Co ltd
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/08Solutions
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41Heterocyclic 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
    • A61K31/41641,3-Diazoles
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/10Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/12Carboxylic acids; Salts or anhydrides thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/16Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
    • A61K47/18Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
    • A61K47/183Amino acids, e.g. glycine, EDTA or aspartame
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/0012Galenical forms characterised by the site of application
    • A61K9/0019Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04Antibacterial agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00Antiparasitic agents
    • A61P33/02Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Dermatology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention discloses an ornidazole injection and a preparation process thereof, wherein the ornidazole injection comprises the following components in parts by weight: 500-1000 g of ornidazole, 1-10 g of cysteine hydrochloride, 500-1000 g of propylene glycol, a proper amount of acetic acid and 3000-6000 ml of water for injection; the preparation process comprises the following steps: adding cysteine hydrochloride, propylene glycol and water for injection into a preparation tank; adding proper amount of acetic acid/sodium acetate; adding ornidazole, stirring and dissolving; sterilizing and filtering to 0.22 μm, sealing ampoule by nitrogen, and sterilizing at 121 deg.C for 15 min. The ornidazole injection adopts cysteine hydrochloride and propylene glycol, so that the solubility of ornidazole in water is improved; through the acetic acid/sodium acetate buffer pair, the adverse reaction caused by the fact that a single pH value regulator is used in the traditional method to enable the pH value of the solution to be too low is avoided, and the stability of the solution under the lower pH value through the use of the buffer pair can be guaranteed.

Description

Ornidazole injection and preparation process thereof
Technical Field
The invention relates to the technical field of medicinal preparations, in particular to an ornidazole injection and a preparation process thereof.
Background
The ornidazole injection is the third generation nitroimidazole antibiotics, which are used for anaerobic bacteria infection, protozoan infection, trichomonad infection and the like. The ornidazole injection is also suitable for:
1. used for treating diseases caused by Bacteroides fragilis, Bacteroides dirichi, Bacteroides ovatus, Bacteroides thetaiotaomicron, Bacteroides vulgatus, Clostridium, Eubacterium, Pediococcus and Pediococcus, helicobacter pylori, Bacteroides melanoides, Fusobacterium, CO2The infectious diseases caused by sensitive anaerobes such as the bacteriophage phagocytosis and the gingival bacteroides comprise: (1) abdominal infection: peritonitis, intra-abdominal abscess, liver abscess, etc.; (2) pelvic infection: endometritis, myometritis, salpingo-ovarian abscess, pelvic cavity soft tissue infection, Haemophilus vaginitis, etc.; (3) oral infection: periodontitis, periapical periodontitis, pericoronitis, acute ulcerative gingivitis, and the like; (4) surgical infection: wound infection, epidermal abscess, decubitus ulcer infection, cellulitis, gas gangrene, etc.; (5) brain infection: meningitis, brain abscesses; (6) and severe anaerobic infection such as septicemia and bacteremia.
2. Can be used for preventing infection before operation and treating anaerobic infection after operation.
3. Can be used for treating severe amebiasis of digestive system, such as amebic dysentery, amebic liver abscess, etc.
The ornidazole injection is a main dosage form of ornidazole drugs, and is widely applied clinically, but the existing ornidazole injection still has the following problems:
(1) ornidazole is easy to dissolve in ethanol and slightly soluble in water; the solubility is increased under an acidic condition, the dissolution condition is greatly improved when the acidity of the solution reaches below 3.0, but the pH value of the solution prepared by clinically using the low-pH-value solution and a glucose solution is still lower, so that the adverse reaction is large when the solution is administrated by intravenous drip, and phlebitis is generated;
(2) there are also documents or patents which prepare the ornidazole injection by adding absolute ethyl alcohol in a prescription, but the absolute ethyl alcohol has great production safety problem, needs an explosion-proof workshop and has high requirement on production environment; and in the production process, the absolute ethyl alcohol is very easy to volatilize, so that the content is not uniform.
Disclosure of Invention
The invention aims to provide an ornidazole injection and a preparation process thereof aiming at the defects and the defects of the prior art, which not only avoids the adverse reaction caused by the fact that the pH value of the solution is too low by using a single pH value regulator in the traditional method, but also can ensure the stability of the solution at a lower pH value by using a buffer pair.
In order to solve the problems in the prior art, the invention adopts the following technical scheme: an ornidazole injection is prepared from the following components in parts by weight: 500-1000 g of ornidazole, 1-10 g of cysteine hydrochloride, 500-1000 g of propylene glycol, 3000-6000 ml of water for injection and acetic acid-sodium acetate buffer; wherein the dosage of the acetic acid-sodium acetate buffer pair ensures that the pH value of the ornidazole injection is 4.8-5.2.
In one embodiment, the invention provides an ornidazole injection, which is prepared from the following components in percentage by weight: 500mg of ornidazole, 1mg of cysteine hydrochloride, 500mg of propylene glycol, 3ml of acetic acid-sodium acetate buffer pair and injection water; wherein the dosage of the acetic acid-sodium acetate buffer pair ensures that the pH value of the ornidazole injection is 4.8-5.2.
In one embodiment, the invention provides an ornidazole injection, which is prepared from the following components in percentage by weight: 500mg of ornidazole, 5mg of cysteine hydrochloride, 1000mg of propylene glycol, acetic acid-sodium acetate buffer pair and 3ml of water for injection; wherein the dosage of the acetic acid-sodium acetate buffer pair ensures that the pH value of the ornidazole injection is 4.8-5.2.
In one embodiment, the invention provides an ornidazole injection, which is prepared from the following components in percentage by weight: 1000mg of ornidazole, 10mg of cysteine hydrochloride, 1000mg of propylene glycol, 6ml of acetic acid-sodium acetate buffer pair and injection water; wherein the dosage of the acetic acid-sodium acetate buffer pair ensures that the pH value of the ornidazole injection is 4.8-5.2.
The invention also provides a preparation process of the ornidazole injection, which comprises the following steps:
(1) adding cysteine hydrochloride, propylene glycol and 60-80% of water for injection in a formula amount into a preparation tank;
(2) adding proper amount of acetic acid and proper amount of sodium acetate;
(3) adding ornidazole, stirring and dissolving;
(4) sterilizing and filtering to 0.22 μm, sealing the ampoule by filling nitrogen, and sterilizing at 121 deg.C for 15 min.
After the technical scheme is adopted, the invention has the following beneficial effects:
the stabilizer cysteine hydrochloride is added in the prescription, the cysteine hydrochloride is a common auxiliary material of the injection, and the cysteine hydrochloride is amino acid normally existing in a human body and is completely nontoxic as a pharmaceutic adjuvant; in addition, the propylene glycol is used as a solubilizer and a cosolvent in the formula, so that the solubility of the ornidazole in water is further improved, and the pH value of the solution is stabilized to about 5.0 through an acetic acid/sodium acetate buffer pair, thereby not only avoiding the adverse reaction caused by the over-low pH value of the solution due to the use of a single pH value regulator in the traditional method, but also ensuring the stability of the solution at a lower pH value through the use of the buffer pair.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is described in further detail below with reference to specific embodiments. It should be understood that the detailed description and specific examples, while indicating the invention, are intended for purposes of illustration only and are not intended to limit the scope of the invention.
Example 1: an ornidazole injection, its prescription is
Figure BSA0000195598890000031
The preparation process comprises the following steps:
(1) firstly, adding 60 percent of water according to the prescription amount;
(2) sequentially adding cysteine hydrochloride, propylene glycol and acetic acid/sodium acetate according to the prescription amount, and stirring for dissolving;
(3) then adding ornidazole, stirring and dissolving to make the pH value of the solution be 4.8,
(4) and adding water for injection to the total amount.
(5) Sterilizing and filtering with 0.22 μm, sealing ampoule with nitrogen, and sterilizing at 121 deg.C for 15 min.
Example 2: an ornidazole injection, its prescription is
Figure BSA0000195598890000041
The preparation process comprises the following steps:
(1) firstly, adding water with the amount of 80 percent of the prescription amount,
(2) sequentially adding cysteine hydrochloride, propylene glycol and acetic acid/sodium acetate according to the prescription amount, stirring and dissolving,
(3) then adding ornidazole, stirring and dissolving to make the pH value of the solution be 5.0,
(4) and adding water for injection to the total amount.
(5) Sterilizing and filtering with 0.22 μm, sealing ampoule with nitrogen, and sterilizing at 121 deg.C for 20 min.
Example 3: an ornidazole injection, its prescription is
Figure BSA0000195598890000042
The preparation process comprises the following steps:
(1) firstly, adding water with the amount of 80 percent of the prescription amount,
(2) sequentially adding cysteine hydrochloride, propylene glycol and acetic acid/sodium acetate according to the prescription amount, stirring and dissolving,
(3) then adding ornidazole, stirring and dissolving to make the pH value of the solution be 5.0,
(4) and adding water for injection to the total amount.
(5) Sterilizing and filtering with 0.22 μm, sealing ampoule with nitrogen, and sterilizing at 121 deg.C for 20 min.
Comparative example 1: an ornidazole injection, its prescription is
Figure BSA0000195598890000051
The preparation process comprises the following steps:
(1) firstly, adding 60 percent of water according to the prescription amount,
(2) adding the propylene glycol with the prescription amount, stirring and dissolving,
(3) then hydrochloric acid is used for adjusting the pH value to 2.5, ornidazole is added, stirring and dissolving are carried out,
(4) and adding water for injection to the total amount.
(5) Sterilizing and filtering with 0.22 μm, sealing ampoule with nitrogen, and sterilizing at 121 deg.C for 20 min.
Comparative example 2: an ornidazole injection, its prescription is
Figure BSA0000195598890000052
The preparation process comprises the following steps:
(1) adding the prescribed amount of propylene glycol and ornidazole into a liquid preparation tank, stirring and dissolving,
(2) and then adding absolute ethyl alcohol to full dose.
(3) Sterilizing and filtering with 0.22 μm, sealing ampoule with nitrogen, and sterilizing at 121 deg.C for 20 min.
The ornidazole injection prepared by the embodiment has a pH value of about 5.0 after being matched with a 5% glucose solution, meets the requirement of an intravenous injection administration route on the pH value of the solution, and the test comparison result is shown in the following table 1; the ornidazole injection prepared by the prescription process has simple and safe preparation process and stable product content, and the test comparison results are shown in the following table 2.
Table 1 results of compatibility with 5% dextrose solution
Traits pH value Comprehensive evaluation
Example 1 Pale yellow clear liquid 5.0 Meets the requirement of the pH value range of the injection
Example 2 Pale yellow clear liquid 5.0 Meets the requirement of the pH value range of the injection
Example 3 Pale yellow clear liquid 4.9 Meets the requirement of the pH value range of the injection
Comparative example 1 Yellow clear liquid 3.6 Out of the pH range of the injection
TABLE 2 quality comparison
Through the research of the preparation of a plurality of batches of samples, the quality condition is as follows
Figure BSA0000195598890000061
Figure BSA0000195598890000071
It will be evident to those skilled in the art that the invention is not limited to the details of the foregoing illustrative embodiments, and that the present invention may be embodied in other specific forms without departing from the spirit or essential attributes thereof. The present embodiments are therefore to be considered in all respects as illustrative and not restrictive, the scope of the invention being indicated by the appended claims rather than by the foregoing description, and all changes which come within the meaning and range of equivalency of the claims are therefore intended to be embraced therein.
Furthermore, it should be understood that although the present description refers to embodiments, not every embodiment may contain only a single embodiment, and such description is for clarity only, and those skilled in the art should integrate the description, and the embodiments may be combined as appropriate to form other embodiments understood by those skilled in the art.

Claims (5)

1. The ornidazole injection is characterized by being prepared from the following components in parts by weight: 500-1000 g of ornidazole, 1-10 g of cysteine hydrochloride, 500-1000 g of propylene glycol, 3000-6000 ml of water for injection and acetic acid-sodium acetate buffer; wherein the dosage of the acetic acid-sodium acetate buffer pair ensures that the pH value of the ornidazole injection is 4.8-5.2.
2. The ornidazole injection as claimed in claim 1, characterised in that it is made up of the following components: 500mg of ornidazole, 1mg of cysteine hydrochloride, 500mg of propylene glycol, acetic acid-sodium acetate buffer pair and 3ml of water for injection; wherein the dosage of the acetic acid-sodium acetate buffer pair ensures that the pH value of the ornidazole injection is 4.8-5.2.
3. The ornidazole injection as claimed in claim 1, characterised in that it is made up of the following components: 500mg of ornidazole, 5mg of cysteine hydrochloride, 1000mg of propylene glycol, acetic acid-sodium acetate buffer pair and 3ml of water for injection; wherein the dosage of the acetic acid-sodium acetate buffer pair ensures that the pH value of the ornidazole injection is 4.8-5.2.
4. The ornidazole injection as claimed in claim 1, characterised in that it is made up of the following components: 1000mg of ornidazole, 10mg of cysteine hydrochloride, 1000mg of propylene glycol, acetic acid-sodium acetate buffer pair and 6ml of water for injection; wherein the dosage of the acetic acid-sodium acetate buffer pair ensures that the pH value of the ornidazole injection is 4.8-5.2.
5. The process for preparing ornidazole injection as claimed in claim 1, characterised in that it comprises the following steps:
(1) adding cysteine hydrochloride, propylene glycol and 60-80% of water for injection in a formula amount into a preparation tank;
(2) adding proper amount of acetic acid and proper amount of sodium acetate;
(3) adding ornidazole, stirring and dissolving;
(4) sterilizing and filtering to 0.22 μm, sealing the ampoule by filling nitrogen, and sterilizing at 121 deg.C for 15 min.
CN201911161579.9A 2019-11-22 2019-11-22 Ornidazole injection and preparation process thereof Pending CN111166718A (en)

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006071912A2 (en) * 2004-12-27 2006-07-06 Johnson & Johnson Consumer Companies, Inc. A method for treating or preventing pruritic and neurogenic skin disorders by applying sertaconazole
CN102335126A (en) * 2010-07-22 2012-02-01 山东方明药业股份有限公司 Ornidazole injection and its preparation method
CN102552127A (en) * 2012-01-31 2012-07-11 石家庄开发区博欣医药科技开发有限公司 Ornidazole injection
CN103040740A (en) * 2013-01-25 2013-04-17 山西普德药业股份有限公司 Ornidazole injection and preparation technology thereof
CN104983678A (en) * 2015-08-04 2015-10-21 山东齐都药业有限公司 Ornidazole infusion preparation and preparation technology thereof
CN107041868A (en) * 2016-02-05 2017-08-15 南京卡文迪许生物工程技术有限公司 A kind of stable ornidazole injection and S-ornidazole injection and preparation method thereof

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006071912A2 (en) * 2004-12-27 2006-07-06 Johnson & Johnson Consumer Companies, Inc. A method for treating or preventing pruritic and neurogenic skin disorders by applying sertaconazole
CN102335126A (en) * 2010-07-22 2012-02-01 山东方明药业股份有限公司 Ornidazole injection and its preparation method
CN102552127A (en) * 2012-01-31 2012-07-11 石家庄开发区博欣医药科技开发有限公司 Ornidazole injection
CN103040740A (en) * 2013-01-25 2013-04-17 山西普德药业股份有限公司 Ornidazole injection and preparation technology thereof
CN104983678A (en) * 2015-08-04 2015-10-21 山东齐都药业有限公司 Ornidazole infusion preparation and preparation technology thereof
CN107041868A (en) * 2016-02-05 2017-08-15 南京卡文迪许生物工程技术有限公司 A kind of stable ornidazole injection and S-ornidazole injection and preparation method thereof

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Application publication date: 20200519