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WO2004000865A1 - Compositions pharmaceutiques d'azithromycine - Google Patents

Compositions pharmaceutiques d'azithromycine Download PDF

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Publication number
WO2004000865A1
WO2004000865A1 PCT/EP2003/006489 EP0306489W WO2004000865A1 WO 2004000865 A1 WO2004000865 A1 WO 2004000865A1 EP 0306489 W EP0306489 W EP 0306489W WO 2004000865 A1 WO2004000865 A1 WO 2004000865A1
Authority
WO
WIPO (PCT)
Prior art keywords
azithromycin
monohydrate
pharmaceutical composition
gram
composition according
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.)
Ceased
Application number
PCT/EP2003/006489
Other languages
English (en)
Inventor
Franz Xaver Schwarz
Johannes Raneburger
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.)
Sandoz AG
Original Assignee
Sandoz AG
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 Sandoz AG filed Critical Sandoz AG
Priority to AU2003279392A priority Critical patent/AU2003279392A1/en
Publication of WO2004000865A1 publication Critical patent/WO2004000865A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
    • C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins

Definitions

  • the present invention relates to organic compounds, such as azithromycin.
  • Azithromycin is a pharmaceutically active compound, e.g. useful as an antibacterial agent, see e.g. The Merck Index, 12th edition, Item 946.
  • a pharmaceutical composition comprising azithromycin in the form of a monohydrate from which azithromycin may be released appropriately and in which azithromycin in the form of a monohydrate is not converted into azithromycin in the form of a dihydrate upon reconsitiution in an aqueous liquid.
  • the present invention provides a pharmaceutical composition for oral administration, comprising, e.g. consisting of
  • Azithromycin in the form of a (stable) monohydrate and its preparation is e.g. disclosed in WO0100640, EP0984020 (azithromycin in the form of a monohydrate isopropanol clathrate) and WO 0210181 , and includes azithromycin in the form of a (stable) monohydrate as claimed in WO0100640, EP0984020 and WO 0210181 , Per gram of azithromycin in the form of a monohydrate preferably - 12.50 to 22.50 gram of a sweetener,
  • a sweetener includes sugars and arteficial sweeteners.
  • a sugar includes one or more sugars, such as saccharose; and an arteficial sweetener includes one or more arteficial sweeteners, such as aspartame.
  • a preferred sweetener includes a sugar and a mixture of a sugar and an artificial sweetener.
  • a sweetener more preferably includes a sugar and optionally an arteficial sweetener in a weight ratio of sugar : arteficial sweetener from 1 :0 to 44:1.
  • a flavourant includes one or more flavourants, e.g. such as flavourants which are commercially available, for example, e.g. selected from the group consisting of, Antiamarum (Flavopharm), Toffee (Silesia) and flavourants available from Firmenich, e.g. Vanilla Cream, Apricot, Golden Syrup, Strawberry, Pinapple, Blackcurrant, Caramel Golden Syrup, Raspberry, Apricot Durarome, Tropical Fruit, Red Fruit.
  • flavourants which are commercially available, for example, e.g. selected from the group consisting of, Antiamarum (Flavopharm), Toffee (Silesia) and flavourants available from Firmenich, e.g. Vanilla Cream, Apricot, Golden Syrup, Strawberry, Pinapple, Blackcurrant, Caramel Golden Syrup, Raspberry, Apricot Durarome, Tropical Fruit, Red Fruit.
  • Flavourant combinations e.g.
  • Antiamarum+Redfruit include Antiamarum+Redfruit, Antiamarum+Toffee, Vanilla Cream+Pinapple, Vanilla Cream+Apricot, Vanilla Cream+Raspberry, preferably Antiamarum (Flavopharm)+Toffee (Silesia), Vanilla Cream+Apricot (both Firmenich).
  • a buffer includes a single buffer substance or a mixture of buffer substances, such as buffers as conventional, preferably Tri-Na-phosphate.
  • a filler includes one or more fillers, e.g. fillers as conventional, preferably SiO 2 , such as Aerosil(s)®.
  • a thickener includes one or more thickeners, e.g. thickeners as conventional, preferably selected from the group consisting of methylcelluloses, e.g. Methylcellulose A4C®., Methocel E3 Premium®, Methocel K 100 M Premium EP®; hydroxypropylcelluloses, e.g. Klucel LF®, carboxymethylcelluloses, e.g. sodium carboxymethylcelluloses, such as Nycel ZSC®, polyvinylpyrrolidones, e.g. Kollidon 90®, natural and artificial gums, e.g. xantham gum; preferably xantham gum+hydroxypropylcellulose.
  • thickeners e.g. thickeners as conventional, preferably selected from the group consisting of methylcelluloses, e.g. Methylcellulose A4C®., Methocel E3 Premium®, Methocel K 100 M Premium EP®; hydroxypropylcelluloses, e.g. Klucel LF
  • a composition according to the present invention may be prepared as appropriate, e.g. according to a method as conventional, such as mixing the ingredients to obtain a homogenous composition.
  • a composition according to the present invention is useful as a suspension powder/granulate, i.e. a powder/granulate which, when reconstituted in a liquid, forms a suspension or emulsion for oral administration.
  • a liquid includes an aqueous liquid, e.g. water.
  • the present invention provides a suspension or emulsion obtainable by mixing a pharmaceutical composition according to the present invention with an aqueous liquid, e.g. water.
  • the present invention provides a pharmaceutical unit dosage form comprising sachets containing a pharmaceutical composition according to the present invention wherein each sachet contains 100 mg, 200 mg or 300 mg, preferably 200 mg, of azithromycin in the form of a monohydrate.
  • azithromycin in the form of a monohydrate may be surprisingly not converted into azithromycin in the form of a dihydrate, even at evelated temperatures, e.g. at 40°C, although it is known that azothromycin in aqueous liquid has a great tendency to form the dihydrate rather than the monohydrate.
  • evelated temperatures e.g. at 40°C
  • azothromycin in aqueous liquid has a great tendency to form the dihydrate rather than the monohydrate.
  • drying of the azithromycin obtained from a suspension sample should be gentle.
  • a suspension for oral administration obtained by reconstitution of a pharmaceutical composition according to the present invention in an aqueous liquid may be subjected to centrifugation, azithromycin obtained may be filtrated off, gently dried e.g. at or slightly above room temperature and the dried powder obtained may be subjected to X-ray diffraction pattern determination.
  • 1.2 g of azithromycin in the form of a monohydrate are mixed with 22.05 g of saccharose powder, 0.04 g xantham gum, 0.04 g of hydroxypropylcellulose (Klucel®), 0.256 g of tri-Na- phosphate, 0.024 g of Siliciumdioxid (Aerosil®); 0.18 g of aspartame and 0.12 g of a flavourant.
  • flavourant Antiamarum Flavipharm + Toffeee (Silesia) or Vanilla Cream (Firmenich)+Apricot (Firmenich) are used.
  • the homogenous mixture obtained is divided into 6 equal portionsand each portion is filled into a separate sachet.
  • 6 sachets containing a suspension granulate for oral administration comprising each 200 mg of azithromycin in the form a monohydrate are obtained.
  • the suspension granulate obtained is reconstituted in water and a suspension is obtained. A part of the suspension is warmed up to 40°. From both suspensions azithromycin is isolated and subjected to X-ray diffraction pattern determination. Azithromycin isolated from both suspension (warmed and unwarmed) is found to be in the form of azithromycin in the form of a monohydrate (and not in the form of a dihydrate).

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Organic Chemistry (AREA)
  • Epidemiology (AREA)
  • Molecular Biology (AREA)
  • Biotechnology (AREA)
  • Biochemistry (AREA)
  • Genetics & Genomics (AREA)
  • Engineering & Computer Science (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Medicinal Preparation (AREA)

Abstract

L'invention concerne une composition pharmaceutique pour administration orale, contenant de l'azithromycine sous forme de monohydrate en tant que principe actif sur le plan pharmaceutique, ainsi qu'un édulcorant, un aromatisant, une solution tampon, éventuellement un support, et éventuellement un épaississant.
PCT/EP2003/006489 2002-06-20 2003-06-18 Compositions pharmaceutiques d'azithromycine Ceased WO2004000865A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2003279392A AU2003279392A1 (en) 2002-06-20 2003-06-18 Pharmaceutical compositions of azithromycin

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB0214277.6A GB0214277D0 (en) 2002-06-20 2002-06-20 Organic compounds
GB0214277.6 2002-06-20

Publications (1)

Publication Number Publication Date
WO2004000865A1 true WO2004000865A1 (fr) 2003-12-31

Family

ID=9938996

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2003/006489 Ceased WO2004000865A1 (fr) 2002-06-20 2003-06-18 Compositions pharmaceutiques d'azithromycine

Country Status (4)

Country Link
AU (1) AU2003279392A1 (fr)
GB (1) GB0214277D0 (fr)
TW (1) TW200400197A (fr)
WO (1) WO2004000865A1 (fr)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004035063A1 (fr) * 2002-10-17 2004-04-29 Sandoz Ag Composition pharmaceutique contenant du monohydrate d'azithromycine
EP1498141A1 (fr) * 2003-07-15 2005-01-19 Pfizer Products Inc. Préparations de suspension orale stables contenant de l'azithromycine non-dihydrate
WO2005002592A3 (fr) * 2003-07-01 2005-02-03 Ranbaxy Lab Ltd Compositions orales stables de monohydrate d'azithromycine
US6984403B2 (en) 2003-12-04 2006-01-10 Pfizer Inc. Azithromycin dosage forms with reduced side effects
WO2006067577A3 (fr) * 2004-12-21 2006-12-28 Pfizer Prod Inc Suspension orales stables d'azithromycine sous forme non dihydrate
US7468428B2 (en) 2004-03-17 2008-12-23 App Pharmaceuticals, Llc Lyophilized azithromycin formulation
US7625507B2 (en) 2003-12-04 2009-12-01 Pfizer Inc. Extrusion process for forming chemically stable drug multiparticulates
US8106111B2 (en) 2009-05-15 2012-01-31 Eastman Chemical Company Antimicrobial effect of cycloaliphatic diol antimicrobial agents in coating compositions

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001000640A1 (fr) * 1999-06-29 2001-01-04 Biochemie S.A. Macrolides
WO2002010181A1 (fr) * 2000-07-31 2002-02-07 Quimica Sintetica, S.A. Monohydrate d'azithromycine a hygroscopicite inferieure, procede relatif a sa preparation et compositions pharmaceutiques le comprenant
WO2002042315A2 (fr) * 2000-11-27 2002-05-30 Biochemie S.A. Solvates macrolides
RU2188018C2 (ru) * 2000-06-20 2002-08-27 Нестерук Владимир Викторович Композиционный состав антибактериального лекарственного средства

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001000640A1 (fr) * 1999-06-29 2001-01-04 Biochemie S.A. Macrolides
RU2188018C2 (ru) * 2000-06-20 2002-08-27 Нестерук Владимир Викторович Композиционный состав антибактериального лекарственного средства
WO2002010181A1 (fr) * 2000-07-31 2002-02-07 Quimica Sintetica, S.A. Monohydrate d'azithromycine a hygroscopicite inferieure, procede relatif a sa preparation et compositions pharmaceutiques le comprenant
WO2002042315A2 (fr) * 2000-11-27 2002-05-30 Biochemie S.A. Solvates macrolides

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004035063A1 (fr) * 2002-10-17 2004-04-29 Sandoz Ag Composition pharmaceutique contenant du monohydrate d'azithromycine
WO2005002592A3 (fr) * 2003-07-01 2005-02-03 Ranbaxy Lab Ltd Compositions orales stables de monohydrate d'azithromycine
EP1498141A1 (fr) * 2003-07-15 2005-01-19 Pfizer Products Inc. Préparations de suspension orale stables contenant de l'azithromycine non-dihydrate
WO2005004920A1 (fr) * 2003-07-15 2005-01-20 Pfizer Products Inc. Suspensions orales stables d'azithromycine non dihydratée
US6984403B2 (en) 2003-12-04 2006-01-10 Pfizer Inc. Azithromycin dosage forms with reduced side effects
US7625507B2 (en) 2003-12-04 2009-12-01 Pfizer Inc. Extrusion process for forming chemically stable drug multiparticulates
US7468428B2 (en) 2004-03-17 2008-12-23 App Pharmaceuticals, Llc Lyophilized azithromycin formulation
WO2006067577A3 (fr) * 2004-12-21 2006-12-28 Pfizer Prod Inc Suspension orales stables d'azithromycine sous forme non dihydrate
US8106111B2 (en) 2009-05-15 2012-01-31 Eastman Chemical Company Antimicrobial effect of cycloaliphatic diol antimicrobial agents in coating compositions

Also Published As

Publication number Publication date
AU2003279392A1 (en) 2004-01-06
GB0214277D0 (en) 2002-07-31
TW200400197A (en) 2004-01-01

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