EP2515849A1 - Effervescent tablet and granule formulation comprising cefixime - Google Patents

Effervescent tablet and granule formulation comprising cefixime

Info

Publication number
EP2515849A1
EP2515849A1 EP10795486A EP10795486A EP2515849A1 EP 2515849 A1 EP2515849 A1 EP 2515849A1 EP 10795486 A EP10795486 A EP 10795486A EP 10795486 A EP10795486 A EP 10795486A EP 2515849 A1 EP2515849 A1 EP 2515849A1
Authority
EP
European Patent Office
Prior art keywords
pharmaceutical composition
composition according
cefixime
binder
effervescent
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.)
Withdrawn
Application number
EP10795486A
Other languages
German (de)
French (fr)
Inventor
Mahmut Bilgic
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Individual
Original Assignee
Individual
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Publication of EP2515849A1 publication Critical patent/EP2515849A1/en
Withdrawn legal-status Critical Current

Links

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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
    • A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/545—Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins, cefaclor, or cephalexine
    • A61K31/546—Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins, cefaclor, or cephalexine containing further heterocyclic rings, e.g. cephalothin
    • 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

Definitions

  • Present invention relates to tablet forms comprising cefixime. Said tablet forms are characterized by being in effervescent form.
  • Cefixime was first described in European patent no EP0030630 (Bl) and it is known with the chemical name of (6R,7R)-7- ⁇ [2-(2-amino-l,3-thiazol-4-yl)-2-
  • carboxylic acid (Formula 1). It is defined as a third generation cephalosporin and indicated for use in the treatment of infections caused by gram positive and gram negative bacteria.
  • Cefixime physically appears as white or light yellow crystal powder. It is freely soluble is methanol and propylene glycol, partially soluble in ethanol and acetone however it does not dissolve in ether, ethyl acetate, hexane and water. Its solubility in aqueous solutions changes with respect to the pH of the solution. Accordingly its solubility in a solution with a pH value of 3.2 is 0.5 mg/mL at room temperature; however when the pH of the solution is increased to 4.2 solubility increases to 18 mg/mL.
  • the product named as SUPRAX that is sold by Fujisawa/Astellas comprises cefixime as active agent and is present in oral tablet or oral suspension forms and in dosages comprising high amounts like 200 mg and 400 mg cefixime.
  • Tablets comprising 200 mg or 400 mg active agents become very big in size when formulated with excipients and this causes problems about use of these tablets for patients having difficulty in swallowing, especially for pediatric and geriatric patients.
  • Suspension forms that are developed to overcome these problems are undesirable since it is possible to take uncontrolled or high dose and in addition to that they have chemical and physical stability problems, have high manufacturing cost, and cause problems when used or when carried.
  • EP0281200 discloses fast dispersing tablets comprising microcrystalline cellulose, microfine cellulose or a mixture thereof in an amount of 24-70 %.
  • Inventors have surprisingly developed a tablet formulation that disperses in water without using cellulose based disintegrants.
  • Subject of the present invention is related to formulation of effervescent tablets and granules comprising cefixime and processes for preparation of these. Surprisingly it was found that effervescent tablets comprising cefixime, which has a low solubility, and formulated with the formulation given in the present invention dissolves in water and forms a homogenous cefixime solution.
  • first aspect of the invention is effervescent tablet and granule formulations comprising cefixime.
  • Second aspect of the invention is use of cefixime in an amount 1-60%, preferably in an amount 5-50% and more preferably in an amount 10-40% in effervescent tablet and granule formulation of the present invention.
  • Cefixime used in the invention can be in monohydrate, dihydrate, trihydrate and/or anhydrous form.
  • Another aspect of the invention is pharmaceutical composition comprising cefixime and in addition to that pharmaceutically acceptable excipients.
  • Said pharmaceutical composition is formulated for effervescent tablet and granule forms. Accordingly, another aspect of the invention relates to pharmaceutical compositions for oral application, comprising cefixime and pharmaceutically acceptable excipients such as effervescent couple, sweetener, binder, water soluble lubricant and flavoring agents and other pharmaceutically acceptable excipients.
  • cefixime and pharmaceutically acceptable excipients such as effervescent couple, sweetener, binder, water soluble lubricant and flavoring agents and other pharmaceutically acceptable excipients.
  • cefixime can be present in an amount of 1-60%
  • effervescent couple can be present in an amount of 10-90%
  • sweetener can be present in an amount of 0.1-5%
  • binder can be present in an amount of 0.1-10%
  • water soluble lubricant can be present in an amount of 0.1-5%
  • flavoring agent can be present in an amount of 0.1-5%.
  • Said effervescent couple can be selected from organic acids such as citric acid, tartaric acid, malic acid, fumaric acid etc., basic agents such as sodium hydrogen carbonate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate etc.
  • Sweetener that can be used in the tablet and granule formulations of the present invention can be selected from a group comprising acesulfame, aspartam, fructose, maltitol, xylitol, saccharine, sodium cyclamate, sucralose, sucrose. Preferably aspartame is used.
  • Water soluble lubricant that can be used in the tablet and granule formulations of the present invention can be selected from a group comprising PEG6000 and sodium benzoate.
  • PEG6000 polyethylene glycol
  • 1-2000 mg of cefixime or its pharmaceutically acceptable salts, hydrates, solvates and/or a combination of these in an amount equivalent to 1-2000 mg cefixime can be used.
  • Binder that can be used in the tablet and granule formulations of the present invention can be selected from a group comprising; ethyl cellulose, gelatine, hypromellose, magnesium aluminium silicate, maltodextrin, polyethylene oxide and povidone.
  • the preferred binder is povidone. It was seen that in tablets in which cefixime :povidone ratio is 20:1, preferably 15:1 and most preferably 10:1 physical qualities such as friability and stability and chemical properties such as solubility and dispersibility have the desired characteristics and that the said ratio plays an important role in obtaining water soluble cefixime effervescent tablets and granules.
  • another aspect of the present invention is effervescent tablet formulations comprising cefixime and povidon in an amount such that cefixime:povidon ratio is 20:1, preferably 15:1 and more preferably 10:1.
  • Another aspect of the invention is use of the pharmaceutical compositions for the treatment of infections caused by gram positive and gram negative bacteria.
  • Another aspect of the invention is related to processes for use in the preparation of effervescent tablet and granules comprising cefixime. Said process comprises use of wet and/or dry granulation techniques present in the state of the art.
  • a process for the preparation of the effervescent tablet or granule according to the present invention comprises granulation of cefixime, effervescent couple, sweetener and binder with water or an aqueous solution, drying of the formed granules, mixing dried granules with flavoring agent and water soluble lubricant and optionally compressing the formed mixture in tablet pressing machine.

Landscapes

  • Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Cephalosporin Compounds (AREA)

Abstract

Present invention relates to tablet forms comprising cefixime. Said tablet forms are characterized by being in effervescent form.

Description

EFFERVESCENT TABLET AND GRANULE FORMULATION COMPRISING
CEFIXIME
Present invention relates to tablet forms comprising cefixime. Said tablet forms are characterized by being in effervescent form.
Background of the invention
Cefixime was first described in European patent no EP0030630 (Bl) and it is known with the chemical name of (6R,7R)-7- {[2-(2-amino-l,3-thiazol-4-yl)-2-
(carboxymethyloxyimino)acetyl] ammo }
carboxylic acid (Formula 1). It is defined as a third generation cephalosporin and indicated for use in the treatment of infections caused by gram positive and gram negative bacteria.
Formula 1
Cefixime physically appears as white or light yellow crystal powder. It is freely soluble is methanol and propylene glycol, partially soluble in ethanol and acetone however it does not dissolve in ether, ethyl acetate, hexane and water. Its solubility in aqueous solutions changes with respect to the pH of the solution. Accordingly its solubility in a solution with a pH value of 3.2 is 0.5 mg/mL at room temperature; however when the pH of the solution is increased to 4.2 solubility increases to 18 mg/mL.
The product named as SUPRAX that is sold by Fujisawa/Astellas comprises cefixime as active agent and is present in oral tablet or oral suspension forms and in dosages comprising high amounts like 200 mg and 400 mg cefixime. Tablets comprising 200 mg or 400 mg active agents become very big in size when formulated with excipients and this causes problems about use of these tablets for patients having difficulty in swallowing, especially for pediatric and geriatric patients. Suspension forms that are developed to overcome these problems are undesirable since it is possible to take uncontrolled or high dose and in addition to that they have chemical and physical stability problems, have high manufacturing cost, and cause problems when used or when carried.
In general although bioavailability values of suspension forms are better compared to the solid dosage forms, the fact that they have a short shelf life like 14 days makes them disadvantageous especially for the patients.
As seen from the above information it is necessary to form new dosage forms in order to provide effective dosing, to meet patient requirements, to provide different alternatives to patients with special requirements such as pediatric and geriatric patients and to provide new dosage forms for use in antibiotic treatment. In order to provide a solution to these problems European patent no EP0281200 (Bl) discloses fast dispersing tablets comprising microcrystalline cellulose, microfine cellulose or a mixture thereof in an amount of 24-70 %.
In another European patent EP0890359 (Bl) dispersible tablet forms comprising 60-85% betalactam antibiotic, 1-10% disintegrant comprising hydroxyl propyl cellulose and/or crospovidone, 0.5-2% binder comprising polyvinyl pyrolidone, hydroxypropyl cellulose or hydroxypropyl methyl cellulose.
When examples present in the state of the art were observed it is seen that it is possible to formulate water dispersible tablet form of cefixime, which is known with its low water solubility, when at least 10% of water swelling/soluble disintegrant or super disintegrants are used.
Inventors have surprisingly developed a tablet formulation that disperses in water without using cellulose based disintegrants.
Detailed description of the invention
Subject of the present invention is related to formulation of effervescent tablets and granules comprising cefixime and processes for preparation of these. Surprisingly it was found that effervescent tablets comprising cefixime, which has a low solubility, and formulated with the formulation given in the present invention dissolves in water and forms a homogenous cefixime solution.
Accordingly, first aspect of the invention is effervescent tablet and granule formulations comprising cefixime. Second aspect of the invention is use of cefixime in an amount 1-60%, preferably in an amount 5-50% and more preferably in an amount 10-40% in effervescent tablet and granule formulation of the present invention.
Cefixime used in the invention can be in monohydrate, dihydrate, trihydrate and/or anhydrous form.
Another aspect of the invention is pharmaceutical composition comprising cefixime and in addition to that pharmaceutically acceptable excipients.
Said pharmaceutical composition is formulated for effervescent tablet and granule forms. Accordingly, another aspect of the invention relates to pharmaceutical compositions for oral application, comprising cefixime and pharmaceutically acceptable excipients such as effervescent couple, sweetener, binder, water soluble lubricant and flavoring agents and other pharmaceutically acceptable excipients.
In tablet and granule composition of the present invention, cefixime can be present in an amount of 1-60%, effervescent couple can be present in an amount of 10-90%, sweetener can be present in an amount of 0.1-5%, binder can be present in an amount of 0.1-10%, water soluble lubricant can be present in an amount of 0.1-5%, flavoring agent can be present in an amount of 0.1-5%.
Said effervescent couple can be selected from organic acids such as citric acid, tartaric acid, malic acid, fumaric acid etc., basic agents such as sodium hydrogen carbonate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate etc. Sweetener that can be used in the tablet and granule formulations of the present invention can be selected from a group comprising acesulfame, aspartam, fructose, maltitol, xylitol, saccharine, sodium cyclamate, sucralose, sucrose. Preferably aspartame is used.
Water soluble lubricant that can be used in the tablet and granule formulations of the present invention can be selected from a group comprising PEG6000 and sodium benzoate. In the tablet and granule formulations of the present invention 1-2000 mg of cefixime or its pharmaceutically acceptable salts, hydrates, solvates and/or a combination of these in an amount equivalent to 1-2000 mg cefixime can be used.
Binder that can be used in the tablet and granule formulations of the present invention can be selected from a group comprising; ethyl cellulose, gelatine, hypromellose, magnesium aluminium silicate, maltodextrin, polyethylene oxide and povidone. As a result of the experiments it was seen that the preferred binder is povidone. It was seen that in tablets in which cefixime :povidone ratio is 20:1, preferably 15:1 and most preferably 10:1 physical qualities such as friability and stability and chemical properties such as solubility and dispersibility have the desired characteristics and that the said ratio plays an important role in obtaining water soluble cefixime effervescent tablets and granules.
In general it is known that water soluble polymer based binders increase the disintegration time of the tablets however unlike what is expected it was seen that effervescent tablets formulated according to the formulation disclosed in the present invention disperses in a short time.
Accordingly, another aspect of the present invention is effervescent tablet formulations comprising cefixime and povidon in an amount such that cefixime:povidon ratio is 20:1, preferably 15:1 and more preferably 10:1.
Another aspect of the invention is use of the pharmaceutical compositions for the treatment of infections caused by gram positive and gram negative bacteria.
Another aspect of the invention is related to processes for use in the preparation of effervescent tablet and granules comprising cefixime. Said process comprises use of wet and/or dry granulation techniques present in the state of the art.
Although not limited with the following example, a process for the preparation of the effervescent tablet or granule according to the present invention comprises granulation of cefixime, effervescent couple, sweetener and binder with water or an aqueous solution, drying of the formed granules, mixing dried granules with flavoring agent and water soluble lubricant and optionally compressing the formed mixture in tablet pressing machine.
Formulation example for effervescent granules:

Claims

1. A pharmaceutical composition comprising cefixime characterized in that it is formulated in the form of effervescent tablets and/or granules.
2. A pharmaceutical composition according to claim 1 wherein cefixime can be in monohydrate, dihydrate, trihydrate or anhydrous form.
3. A pharmaceutical composition according to claim 1 wherein said composition comprises cefixime in an amount of 1-50%, preferably 5-40%, more preferably 10-30% by weight compared to the total weight of the unit dose.
4. A pharmaceutical composition according to claim 1 wherein said composition comprises pharmaceutically acceptable excipients in addition to the cefixime that is used as an active agent.
5. A pharmaceutical composition according to claim 4 wherein said composition comprises effervescent couple, sweetener, binder, water soluble lubricant and flavoring agents in addition to cefixime that is used as the active agent.
6. A pharmaceutical composition according to claim 5 wherein effervescent couple can be selected from a group comprising citric acid, tartaric acid, malic acid etc. as organic acids and sodium hydrogen carbonate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate as basic agent and combinations thereof.
7. A pharmaceutical composition according to claim 6 wherein effervescent couple comprises citric acid and sodium hydrogen carbonate.
8. A pharmaceutical composition according to claim 5 wherein sweetener is selected from a group comprising acesulfame, aspartam, fructose, maltitol, xylitol, saccharine, sodium cyclamate, sucralose, sucrose.
9. A pharmaceutical composition according to claim 5 wherein binder is selected from a group comprising ethyl cellulose, gelatin, hypromellose, magnesium aluminum silicate, maltodextrin, polyethylene oxide and povidone.
10. A pharmaceutical composition according to claim 9 wherein preferred binder is povidone.
11. A pharmaceutical composition according to claim 5 wherein water soluble lubricant is selected from a group comprising PEG 6000 and sodium benzoate.
12. A pharmaceutical composition according to claim 1 wherein cefixime :povidone ratio is 20:1, preferably 15:1 and more preferably 10:1.
13. A pharmaceutical composition according to any of the preceding claims wherein said composition may comprise 1-60% cefixime and/or its pharmaceutically acceptable derivatives, 10-90 % of effervescent couple 0.1-5% sweetener, 0.1-10% binder, 0.1-5 water soluble lubricant and 0.1-5% flavoring agent.
14. A process for the preparation of the pharmaceutical composition according to any of the preceding claims wherein said process comprises granulation of cefixime, effervescent couple, sweetener and binder and then mixing formed granules with flavoring agent and water soluble lubricant and optionally compressing in the form of tablets.
15. A pharmaceutical composition according to claim 1 for use in the treatment of infections caused by gram positive and gram negative bacteria.
EP10795486A 2009-12-25 2010-12-03 Effervescent tablet and granule formulation comprising cefixime Withdrawn EP2515849A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
TR2009/09786A TR200909786A1 (en) 2009-12-25 2009-12-25 Effervescent tablet and granule formulation containing cefixime.
PCT/TR2010/000241 WO2011078821A1 (en) 2009-12-25 2010-12-03 Effervescent tablet and granule formulation comprising cefixime

Publications (1)

Publication Number Publication Date
EP2515849A1 true EP2515849A1 (en) 2012-10-31

Family

ID=43532584

Family Applications (1)

Application Number Title Priority Date Filing Date
EP10795486A Withdrawn EP2515849A1 (en) 2009-12-25 2010-12-03 Effervescent tablet and granule formulation comprising cefixime

Country Status (3)

Country Link
EP (1) EP2515849A1 (en)
TR (2) TR200909786A1 (en)
WO (2) WO2011078821A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111544412A (en) * 2020-04-17 2020-08-18 广州白云山医药集团股份有限公司白云山制药总厂 Cefixime composition and preparation method thereof

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8962041B2 (en) 2013-02-12 2015-02-24 Johnson & Johnson Consumer Companies, Inc. Methods and compositions for enhancing hair quality using blackberry extract
CN103494821B (en) * 2013-10-01 2018-09-25 迪沙药业集团有限公司 A kind of cefixime composition
CN104366648A (en) * 2014-10-21 2015-02-25 宣城柏维力生物工程有限公司 Sweet orange VC (Vitamin C) effervescent tablet
CN113440530B (en) * 2021-07-08 2023-08-08 广州白云山医药集团股份有限公司白云山制药总厂 Cefixime medicine and preparation method thereof

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US4409214A (en) 1979-11-19 1983-10-11 Fujisawa Pharmaceutical, Co., Ltd. 7-Acylamino-3-vinylcephalosporanic acid derivatives and processes for the preparation thereof
DE3887179T2 (en) 1987-03-02 1994-06-16 Brocades Pharma Bv Pharmaceutical composition, pharmaceutical granules and process for their preparation.
ATE216887T1 (en) 1996-02-29 2002-05-15 Fujisawa Pharmaceutical Co TABLETS CONTAINING BETA-LACTAM ANTIBIOTIC AND METHOD FOR THE PRODUCTION THEREOF
CN100417383C (en) * 2006-03-07 2008-09-10 中国药科大学 A kind of effervescent tablet containing cefixime and its preparation method
CN101606913B (en) * 2009-07-16 2012-12-19 广州白云山制药股份有限公司广州白云山制药总厂 Cefixime dispersing tablet and preparation methods thereof

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111544412A (en) * 2020-04-17 2020-08-18 广州白云山医药集团股份有限公司白云山制药总厂 Cefixime composition and preparation method thereof
CN111544412B (en) * 2020-04-17 2022-06-24 广州白云山医药集团股份有限公司白云山制药总厂 Cefixime composition and preparation method thereof

Also Published As

Publication number Publication date
WO2011078832A1 (en) 2011-06-30
TR200909786A1 (en) 2011-07-21
TR201003856A1 (en) 2011-08-22
WO2011078821A1 (en) 2011-06-30

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