WO2007017895A2 - Compositions pharmaceutiques stabilisees de cephalosporines - Google Patents

Compositions pharmaceutiques stabilisees de cephalosporines Download PDF

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Publication number
WO2007017895A2
WO2007017895A2 PCT/IN2006/000160 IN2006000160W WO2007017895A2 WO 2007017895 A2 WO2007017895 A2 WO 2007017895A2 IN 2006000160 W IN2006000160 W IN 2006000160W WO 2007017895 A2 WO2007017895 A2 WO 2007017895A2
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WO
WIPO (PCT)
Prior art keywords
pharmaceutical composition
cephalosporin
maize starch
oral
stability
Prior art date
Application number
PCT/IN2006/000160
Other languages
English (en)
Other versions
WO2007017895A3 (fr
Inventor
Himadri Sen
Makarand Avachat
Sanjay Wagh
Bharat Metkar
Abhijit Dhamne
Original Assignee
Lupin Limited
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 Lupin Limited filed Critical Lupin Limited
Priority to EP06809918A priority Critical patent/EP1883393A2/fr
Priority to JP2008509579A priority patent/JP2008540403A/ja
Publication of WO2007017895A2 publication Critical patent/WO2007017895A2/fr
Publication of WO2007017895A3 publication Critical patent/WO2007017895A3/fr

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Classifications

    • 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
    • A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
    • A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
    • 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
    • A61K9/10—Dispersions; Emulsions

Definitions

  • the invention relates to oral pharmaceutical compositions of cephalosporins, particularly Cefpodoxime and a method for enhancing the stability of these oral pharmaceutical compositions.
  • Cephalosporins are one of the mainstays of antibacterial therapy today.Cefpodoxime proxetil, (R, S)-i-(isopropoxycarbonyloxy) ethyl - (+)-(6R, 7R)-7-[2-(2-amino-4-thiazolyl)-2-((Z)-methoxyimino)acetamido]-3- methoxymethyl-8-oxo-5-thia-1 -azabicyclo [4,2,0]oct-2-en-2- carboxylate, disclosed in U.S. Pat. No.
  • 4,486,425 is a cephalosporin ester pro-drug which, when orally administered, is absorbed and de-esterified through rapid hydrolysis by esterases present on the intestinal mucosa to release its active metabolite, the third generation cephalosporin, cefpodoxime, an antibacterial agent.
  • Cefpodoxime Proxetil is a valuable antibiotic characterized by high broad- spectrum activity against gram-positive and gram-negative microorganisms. Cefpodoxime exhibits a high degree of ⁇ - lactamase stability and is stable towards hydrolysis by the most commonly found plasmid-mediated ⁇ - lactamases. It shares the familiar and relatively benign tolerability profile of other broad spectrum cephalosporins with regard to both the incidence and severity of adverse events thus, rendering it as an effective alternative to currently used ⁇ - lactams for empirical therapy in a wide range of community acquired infections in both adult and pediatric patients.
  • Cefpodoxime proxetil is a .highly hydrophobic drug that has a tendency to form a gel in aqueous media, which thereby results in slow dissolution and hence poor bioavailability. It is therefore necessary that the pharmaceutical composition be formulated such that bridging of molecules to form a gel is prevented and thereby, the dissolution is improved. Apart from ensuring bioavailability, a pharmaceutical dosage form also needs to be stable. The stabilization of cephalosporins such as cefpodoxime, which are highly prone to degradation in the presence of moisture and temperature, is a challenging task for the formulator. The applicants have now surprisingly found that the use of maize starch with moisture content of not more than 2% in oral, pharmaceutical compositions comprising Cefpodoxime proxetil significantly improves stability. •
  • Another object of the invention is to provide a process for preparing an oral, stable, pharmaceutical composition of a cephalosporin comprising the steps of reducing the size of the cephalosporin particles and mixing with maize starch and one or more excipients.
  • Another object of the invention is to provide a process for preparing an oral, stable, pharmaceutical composition of Cefpodoxime proxetil comprising the steps of reducing the size of the cefpodoxime proxetil particles and mixing with maize starch and one or more excipients.
  • cephalosporins include, but are not limited to Cefixime, cefpodoxime proxetil, cefuroxime axetil, Cefdinir, cefaclor, cephalexin and the like.
  • cefpodoxime covers cefpodoxime base and the esters of cefpodoxime such as cefpodoxime proxetil and these terms are interchangeable.
  • the maize (corn) starch used has moisture content of not more than 2% (low moisture containing maize or corn starch).
  • the low moisture containing starch is maize (corn) starch (e.g. marketed under the brand name of Unipure FL) that has been carefully dried under controlled conditions to meet moisture specifications that is lower than that found in conventional starches.
  • the maize starch with moisture content of not more than 2% can be used in a stability- enhancing amount.
  • stability enhancing amount is meant an amount which stabilizes a cephalosporin, particularly cefpodoxime proxetil in a composition as compared to a composition which does not contain maize starch and this amount can range from 1-99%.
  • the maize starch with moisture content of not more than 2% can be used in a range from 5 to 50%.
  • dosage form' includes within its scope but is not limited to tablets, capsules, suspensions, suppositories, semisolid preparations and the like.
  • dosage forms can additionally comprise one or more excipients, which are well known to the person skilled in the art.
  • Processes well known to the person skilled in the art can be used to prepare these dosage forms e.g. a process for preparing an oral, stable, pharmaceutical composition of a cephalosporin can comprise the steps of reducing the size of the cephalosporin particles and mixing with maize starch and one or more excipients.
  • a process for preparing an oral, stable, pharmaceutical composition of Cefpodoxime proxetil can comprise the steps of reducing the size of the cefpodoxime proxetil particles and mixing with maize starch and one or more excipients.
  • a preferred embodiment involves the use of maize starch with moisture content of not more than 2% in an oral, pharmaceutical suspension composition of cephalosporins particularly, Cefpodoxime proxetil.
  • composition includes within its scope but is not limited to compositions selected from the group consisting of pellets for suspension which can be coated or uncoated, granules for suspension, in the form of a unit dose packet (sometimes referred to in the art as a "sachet"), in the form of a suspension made from a unit dose packet, in the form of a powder for oral suspension, in the form of a dose sipping device and in the form of an oral suspension per se and combinations of these e.g. coated pellets filled in a dose sipping device or in a sachet.
  • a unit dose packet sometimes referred to in the art as a "sachet”
  • suspension when a unit dose packet is constituted, it is probably mainly in the form of a suspension if reconstituted according to directions, although the extent of suspension versus solution depends on a number of factors such as pH.
  • the use of the term "suspension” herein is intended to embrace liquids containing cefpodoxime axetil partially in suspension and partially in solution.
  • a further preferred embodiment involves the use of maize starch with a moisture content of not more than 2% in a powder for suspension composition of cephalosporins, particularly cefpodoxime proxetil.
  • the oral, pharmaceutical suspension composition can additionally comprise of atleast one excipient depending upon the dosage form e.g. whether as pellets or as granules for suspension and so on.
  • the excipient can be one or more selected from the group consisting of diluents, binders, disintegrants, stabilizers, wetting agents, sweeteners, thickening agents, dispersing agents, pH - stabilizing agents, flavoring agents, taste - enhancing agents, preservatives, coloring agents, lubricants and flow - aids and the like.
  • One excipient can perform more than one function.
  • Diluents which include, but are not limited to mannitol, sucrose, starch, lactose, dicalcium phosphate, xylitol, sorbitol, micro-crystalline cellulose and the like can be used.
  • Binders which include, but are not limited to, alkylcelluloses such as methyl cellulose, hydroxyalkylcelluloses such as hydroxypropylcellulose, low substituted hydroxypropylcellulose and hydroxypropyl methylcellulose, sodium carboxymethylcellulose or mixtures thereof, pregelatinised maize starch or polyvinylpyrrolidone can be used.
  • Disintegrants which include but are not limited to, crospovidone, sodium starch glycolate, starches such as maize starch and dried starch, croscarmellose sodium and cellulose products such as microcrystalline cellulose, microfine cellulose, low substituted hydroxypropylcellulose and the like.
  • Suitable wetting agents can include, but are not limited to, surfactants, either singly or in admixture. Examples of surfactants include, but are not limited to, the polysorbates, sodium lauryl sulphate, poloxamers and the like.
  • Suitable sweeteners include, but are not limited to, natural sweeteners such as sugars e.g. fructose, glucose, sucrose, sugar alcohols such as mannitol, sorbitol or mixtures thereof and artificial sweeteners such as sodium saccharine, sodium cyclamate and aspartame.
  • natural sweeteners such as sugars e.g. fructose, glucose, sucrose, sugar alcohols such as mannitol, sorbitol or mixtures thereof
  • artificial sweeteners such as sodium saccharine, sodium cyclamate and aspartame.
  • Suitable thickening agents function as suspending agents and include, but are not limited to, hydrocolloid gums known for such purpose, examples of which include xanthan gum, guar gum, locust bean gum, gum tragacanth, microcrystalline cellulose and carboxymethylcellulose sodium, sodium carboxymethylcellulose, polyvinylpyrrolidone, hydroxypropylcellulose and the like or mixtures thereof.
  • Dispersing agents include, but are not limited to, colloidal silicon dioxide and surfactants, wherein the surfactant is used alone or as an admixture with one or more surfactant. Combinations of colloidal silicon dioxide with one or more surfactants can also be used.
  • the oral, pharmaceutical suspension composition may also contain a pH - stabilizing agent to maintain a desired pH upon reconstitution, as discussed above.
  • a pH - stabilizing agent encompasses buffers and pH - altering agents. Suitable pH - stabilizing agents include tribasic sodium phosphate, anhydrous sodium carbonate, glycine, citric acid and the like or mixtures thereof.
  • Flavouring agents are well known to persons skilled in the art and include, but are not limited to fruity flavours. Banana Flavour or combinations thereof with other flavours are preferred.
  • Taste enhancing agents include, but are not limited to, sodium chloride, glycine, citric acid, tartaric acid and the like and mixtures thereof.
  • Suitable preservatives include, but are not limited to, benzoic acid and sorbic acid and their salts, methyl paraben, butylparaben, propylparaben and the like.
  • Suitable coloring agents include, but are not limited to, titanium dioxide pigments, lake colours and iron oxide pigments.
  • Lubricants and flow aids such as, but not limited to, talc, magnesium stearate, calcium silicate and colloidal silicon dioxide can also be used.
  • oral suspension compositions can be prepared by means well known to those skilled in the art.
  • the powder for suspension formulations can be prepared by a process comprising the steps of reducing the size of the cephalosporin and mixing with one or more excipients selected from the group consisting of diluents, binders, d is integrants, stabilizers, wetting agents, sweeteners, thickening agents, dispersing agents, pH - stabilizing agents, flavoring agents, taste - enhancing agents, preservatives, coloring agents, lubricants and flow - aids and the like.
  • excipients selected from the group consisting of diluents, binders, d is integrants, stabilizers, wetting agents, sweeteners, thickening agents, dispersing agents, pH - stabilizing agents, flavoring agents, taste - enhancing agents, preservatives, coloring agents, lubricants and flow - aids and the like.
  • the powder for suspension formulations can be prepared by a process comprising the steps of reducing the size of Cefpodoxime proxetil and mixing with one or more excipients selected from the group consisting of diluents, binders, disintegrants, stabilizers, wetting agents, sweeteners, thickening agents, dispersing agents, pH - stabilizing agents, flavoring agents, taste - enhancing agents, preservatives, coloring agents, lubricants and flow - aids and the like.
  • excipients selected from the group consisting of diluents, binders, disintegrants, stabilizers, wetting agents, sweeteners, thickening agents, dispersing agents, pH - stabilizing agents, flavoring agents, taste - enhancing agents, preservatives, coloring agents, lubricants and flow - aids and the like.
  • the suspension can be reconstituted using potable water or using juices such as apple juice, strawberry juice, orange juice or using aerated or carbonated preparations.
  • juices such as apple juice, strawberry juice, orange juice or using aerated or carbonated preparations.
  • vehicles well known to persons skilled in the art such as propylene glycol, glycerin, sorbitol, liquid glucose and the like can also be used, at levels well known to the persons skilled in the art, in addition to water.
  • the invention provides for an oral, pharmaceutical composition, which is stable and has adequate bioavailability, the composition comprising a cephalosporin particularly cefpodoxime proxetil and maize starch.
  • a cephalosporin particularly cefpodoxime proxetil and maize starch By 'adequate bioavailability' is meant a composition which is bioequivalent to the commercially available oral, pharmaceutical compositions of cephalosporins particularly cefpodoxime proxetil.
  • Cefpodoxime proxetil was micronized and sifted using an appropriate screen on a vibratory sifter.
  • Table 1 Comparison of the stability profile of powder for oral suspension of Cefpodoxime proxetil formulation I (with maize starch) and formulation Il (without maize starch) immediately after reconstitution and 10 days after reconstitution

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  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)

Abstract

L'invention concerne des compositions pharmaceutiques orales de céphalosporines, et notamment du cefpodoxime, un procédé pour leur préparation et un procédé destiné à renforcer la stabilité de ces compositions pharmaceutiques orales. La composition pharmaceutique orale d'une céphalosporine est stable et présente une biodisponibilité adéquate, et comprend une céphalosporine ainsi que de l'amidon de maïs. Le procédé de préparation d'une composition pharmaceutique orale d'une céphalosporine consiste à réduire la taille de la céphalosporine et à la mélanger avec de l'amidon de maïs et un ou plusieurs excipients. Le procédé destiné à renforcer le profil de stabilité d'une céphalosporine dans une composition pharmaceutique consiste à mettre la céphalosporine en contact avec une dose renforçant la stabilité d'amidon de maïs présentant une teneur en humidité inférieure ou égale à 2 %. La suspension orale présente un profil de stabilité amélioré par comparaison avec une composition pharmaceutique en suspension orale comprenant ladite céphalosporine mais ne contenant pas d'amidon de maïs en dose renforçant la stabilité.
PCT/IN2006/000160 2005-05-05 2006-05-05 Compositions pharmaceutiques stabilisees de cephalosporines WO2007017895A2 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP06809918A EP1883393A2 (fr) 2005-05-05 2006-05-05 Compositions pharmaceutiques stabilisees de cephalosporines
JP2008509579A JP2008540403A (ja) 2005-05-05 2006-05-05 セファロスポリンの安定化経口用医薬組成物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN556MU2005 2005-05-05
IN556/MUM/2005 2005-05-05

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WO2007017895A2 true WO2007017895A2 (fr) 2007-02-15
WO2007017895A3 WO2007017895A3 (fr) 2007-04-19

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WO (1) WO2007017895A2 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012060788A1 (fr) * 2010-11-05 2012-05-10 Mahmut Bilgic Formulations de céphalosporines avec teneur en humidité contrôlée
WO2012060786A3 (fr) * 2010-11-05 2012-07-26 Mahmut Bilgic Formulations de proxétil cefpodoxime comprenant un agent de viscosité
WO2012026908A3 (fr) * 2010-08-25 2012-09-07 Mahmut Bilgic Préparations de cefpodoxime proxétil comprenant un agent régulateur de goût
WO2012026907A3 (fr) * 2010-08-25 2012-09-13 Mahmut Bilgic Préparations de cefpodoxime proxétil
WO2015007571A1 (fr) * 2013-07-18 2015-01-22 Sandoz Ag Mélanges de poudres pour formulations de sirop sec antibiotique
WO2017046756A1 (fr) * 2015-09-18 2017-03-23 Lupin Limited Esters de céfixime proxétil et axétil

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013147488A (ja) * 2011-12-21 2013-08-01 Taisho Pharmaceutical Co Ltd 固形製剤
CN103479589B (zh) * 2013-09-22 2016-04-13 海南葫芦娃制药有限公司 头孢泊肟酯分散片及其制备方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1132583A (en) * 1964-12-16 1968-11-06 Glaxo Lab Ltd Pharmaceutical compositions containing cephalosporins
US3931404A (en) * 1972-12-06 1976-01-06 Hoechst Aktiengesellschaft High dosage orally administrable cephalosporin antibiotic preparations
US3945994A (en) * 1973-02-08 1976-03-23 Gist-Brocades N.V. Novel acid compounds
WO2002067943A1 (fr) * 2001-02-27 2002-09-06 Ranbaxy Laboratories Limited Composition pharmaceutique orale de cefpodoxime-proxetil
WO2004022727A1 (fr) * 2002-09-06 2004-03-18 Vri Biomedical Ltd Bacterie probiotique : lactobacillus fermentum

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1132583A (en) * 1964-12-16 1968-11-06 Glaxo Lab Ltd Pharmaceutical compositions containing cephalosporins
US3931404A (en) * 1972-12-06 1976-01-06 Hoechst Aktiengesellschaft High dosage orally administrable cephalosporin antibiotic preparations
US3945994A (en) * 1973-02-08 1976-03-23 Gist-Brocades N.V. Novel acid compounds
WO2002067943A1 (fr) * 2001-02-27 2002-09-06 Ranbaxy Laboratories Limited Composition pharmaceutique orale de cefpodoxime-proxetil
WO2004022727A1 (fr) * 2002-09-06 2004-03-18 Vri Biomedical Ltd Bacterie probiotique : lactobacillus fermentum

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012026908A3 (fr) * 2010-08-25 2012-09-07 Mahmut Bilgic Préparations de cefpodoxime proxétil comprenant un agent régulateur de goût
WO2012026907A3 (fr) * 2010-08-25 2012-09-13 Mahmut Bilgic Préparations de cefpodoxime proxétil
WO2012060788A1 (fr) * 2010-11-05 2012-05-10 Mahmut Bilgic Formulations de céphalosporines avec teneur en humidité contrôlée
WO2012060786A3 (fr) * 2010-11-05 2012-07-26 Mahmut Bilgic Formulations de proxétil cefpodoxime comprenant un agent de viscosité
WO2012060790A3 (fr) * 2010-11-05 2012-09-20 Mahmut Bilgic Formulations de cefpodoxime proxétil dispersibles dans l'eau
WO2015007571A1 (fr) * 2013-07-18 2015-01-22 Sandoz Ag Mélanges de poudres pour formulations de sirop sec antibiotique
CN105377236A (zh) * 2013-07-18 2016-03-02 桑多斯股份公司 用于抗生素干糖浆制剂的粉末混合物
US9566337B2 (en) 2013-07-18 2017-02-14 Sandoz Ag Powder mixtures for antibiotic dry syrup formulations
AU2014292314B2 (en) * 2013-07-18 2019-03-07 Sandoz Ag Powder mixtures for antibiotic dry syrup formulations
CN105377236B (zh) * 2013-07-18 2019-04-23 桑多斯股份公司 用于抗生素干糖浆制剂的粉末混合物
WO2017046756A1 (fr) * 2015-09-18 2017-03-23 Lupin Limited Esters de céfixime proxétil et axétil

Also Published As

Publication number Publication date
JP2008540403A (ja) 2008-11-20
WO2007017895A3 (fr) 2007-04-19
EP1883393A2 (fr) 2008-02-06

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