WO1995033487A1 - Formulations injectables contenant un dessiccatif - Google Patents

Formulations injectables contenant un dessiccatif Download PDF

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Publication number
WO1995033487A1
WO1995033487A1 PCT/EP1995/002127 EP9502127W WO9533487A1 WO 1995033487 A1 WO1995033487 A1 WO 1995033487A1 EP 9502127 W EP9502127 W EP 9502127W WO 9533487 A1 WO9533487 A1 WO 9533487A1
Authority
WO
WIPO (PCT)
Prior art keywords
desiccant
pharmaceutical formulation
formulation
desiccating
formulation according
Prior art date
Application number
PCT/EP1995/002127
Other languages
English (en)
Inventor
Teodoro Fonio
Marco Pesatori
Original Assignee
Smithkline Beecham Farmaceutici S.P.A.
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 Smithkline Beecham Farmaceutici S.P.A. filed Critical Smithkline Beecham Farmaceutici S.P.A.
Priority to JP8500355A priority Critical patent/JPH10500975A/ja
Priority to EP95922497A priority patent/EP0764031A1/fr
Publication of WO1995033487A1 publication Critical patent/WO1995033487A1/fr

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Classifications

    • 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
    • A61K47/02—Inorganic compounds
    • 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
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
    • 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
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner

Definitions

  • compositions suitable for parenteral administration which term includes injection and infusion, e.g intravenously (i.v.) or intramuscularly (i.m.), are normally available as ready to use solutions and suspensions provided in sealed vials or ampoules, or as solid formulations, e.g. granules and powders, provided in sealed vials ready for reconstitution with an aqueous medium such as sterile water.
  • moisture sensitive formulations are those which include pharmaceutically acceptable derivatives of the ⁇ -lactamase inhibitor clavulanic acid (hereinafter referred to as "clavulanate” unless specific derivatives are identified), such as its salts, particularly potassium clavulanate, which is very moisture sensitive.
  • clavulanate pharmaceutically acceptable derivatives of the ⁇ -lactamase inhibitor clavulanic acid
  • potassium clavulanate which is very moisture sensitive.
  • Potassium clavulanate is frequently co-formulated with ⁇ -lactam antibiotics in injectable formulations, such as with injectable forms of amoxycillin, for example sodium amoxycillin.
  • a pharmaceutical formulation comprising a moisture sensitive pharmaceutically active material and a desiccant material, the desiccant being both water soluble and pharmaceutically acceptable by parenteral administration.
  • the present invention also provides a method of preparing such a formulation, comprising the steps of admixing a moisture sensitive pharmaceutically active material and a desiccant, the desiccant being both water soluble and pharmaceutically acceptable by injection or infusion.
  • the present invention also provides such a formulation for use as an active therapeutic substance.
  • the present invention also provides the use of such a formulation in the preparation of a medicament.
  • the present invention also provides a method for protecting a moisture sensitive pharmaceutically active material from degradation by moisture by the use of a desiccant material which is both water soluble and pharmaceutically acceptable by parenteral administration.
  • the present invention also provides a method of treatment of a human patient which includes the step of the parenteral administration to a patient in need of such treatment of a formulation as described above.
  • the desiccant excercises a desiccant effect upon the moisture sensitive pharmaceutically active material and thereby protects it against the effects of moisture.
  • the formulation may be made up into solution together with the active material for parenteral adminsitration, for example via i.v. or i.m. administration.
  • the formulation of the invention is suitable for parenteral administration.
  • the moisture sensitive pharmaceutically active material is preferably one which is suitable for parenteral administration.
  • the formulation of the invention may additionaly include pharmaceutically active material(s) which are stable to moisture and which are suitable for parenteral administration.
  • the invention is particularly suitable for use in formulations wherein the moisture sensitive pharmaceutically active material is clavulanate, particularly potassium clavulanate.
  • the clavulanate may be co-formulated with an injectable antibiotic, suitably a ⁇ -lactam antibiotic, such as a penicillin or cephalosporin, so that the formulation is suitable for use in the treatment of bacterial infections.
  • the antibiotic may be in a crystalline form, and may also be moisture sensitive, or may be stable toward moisture.
  • Preferred ⁇ -lactam antibiotics are amoxycillin and ticarcillin in the form of respectively sodium amoxycillin and sodium ticarcillin.
  • a particular form of sodium amoxycillin for which the present invention is suitable is crystalline sodium amoxycillin, particularly anhydrous crystalline sodium amoxycillin, for example the crystalline sodium amoxycillin disclosed in EP 0131147, the contents of which are included by way of reference.
  • the ratio potassium clavulanate : antibiotic may vary within known broad limits, typically between 1 : 1 and 1 : 30, particularly between 1 : 1 and 1 : 12 in the case of sodium amoxycillin, for example between 1 : 1 and 1 : 8, these ratios being expressed in terms of the free acid equivalents.
  • the quantities of active materials may be present in unit or multiple unit dosage amounts, corresponding to the quantities in which they are used in known injectable formulations.
  • injectable potassium clavulanate sodium amoxycillin formulations 100 mg clavulanic acid : 500 mg amoxycillin, or 200 mg clavulanic acid : 1000 mg amoxycillin, provided respectively as potassium clavulanate and sodium amoxycillin may be used in unit dosage or multiple unit dosage formulations.
  • a suitable desiccant is a desiccating metal salt which is water soluble and pharmaceutically acceptable when administered by injection.
  • such salts which have been found to be suitable, particularly for formulations which comprise clavulanate, for example co-formulations of potassium clavulanate and crystalline sodium amoxycillin, include Group I and Group II metal chlorides or mixtures thereof, such as desiccating forms of sodium chloride, calcium chloride and magnesium chloride.
  • a suitable desiccating form of sodium chloride is an amorphous form for example obtainable by spray-drying and containing a low moisture content.
  • a suitable desiccating form of calcium chloride is an at least partly dehydrated form, e.g containing 5% or less of water, for example obtainable by heat treatment under vacuum.
  • a suitable desiccating form of magnesium chloride is an at least partly dehydrated form, for example obtainable by heat treatment under vacuum.
  • metal salts which may be suitable include disodium phosphate in an at least partly anhydrous form e,g containing around 0.1% water. Such salts may be used singly or in mixtures, for example a mixture of sodium chloride and magnesium chloride.
  • a desiccating metal salt needed to provide adequate desiccation of the pharmaceutical formulation of the invention will depend upon the components of the formulation and in particular on the nature of the moisture sensitive active material.
  • 2200 mg of a 10: 1 sodium amoxycillin : potassium clavulanate blend (ratio expressed as weights of free acids equivalent) contained in a sealed vial for injectable administration may be suitably protected by 50 mg or less , e.g 35 - 15 mg of magnesium chloride, or by 200 mg or less, e.g 100 mg or less, of sodium chloride, or by 100 mg or less of a 95:5 w:w mixture of sodium chloride and magnesium chloride, or by 100 mg or less, e.g 50 mg or less of calcium chloride.
  • Another suitable desiccant is a desiccating carbohydrate which is water soluble and pharmaceutically acceptable when administered by injection.
  • desiccating carbohydrates include lactose (particularly in a spray-dried form) sorbitol, and glucose, in an at least partly dehydrated state, for example obtainable by heat treatment under vacuum. Lactose is a preferred desiccating carbohydrate.
  • Desiccating carbohydrates may be used singly, or mixtures of desiccating carbohydrates may be used, or mixtures of one or more desiccating carbohydrates with one or more of the above-described desiccating metal salts may be used.
  • a desiccating carbohydrate needed to provide adequate desiccation of the pharmaceutical formulation of the invention will again depend upon the components of the formulation and in particular on the nature of the moisture sensitive active material.
  • 2200 mg of a 10:1 sodium amoxycillin : potassium clavulanate blend (ratio expressed as weights of free acids equivalent) contained in a sealed vial for injectable administration may be suitably protected by 500 mg or less of a desiccating form of glucose, sorbitol or spray-dried lactose.
  • Another suitable desiccant is a desiccating form of a polyvinylpyrrolidone ("PVP") polymer, such as the polymers commercially available as Kollidon 17 PF TM and Kollidon 12 PF TM.
  • PVP polyvinylpyrrolidone
  • the use of PVP in the form of Kollidon PF 12 TM together only with sodium amoxycillin in injectable pharmaceutical formulations to improve the stability of the sodium amoxycillin when the formulation has been reconstituted has previously been disclosed in EP 0012495 A and EP 0012496 A.
  • the PVP is not functioning as a desiccant in such formulations, as EP 0012495 states that the PVP may even be provided as an aqueous solution.
  • EP 0012495 discloses a formulation comprising 250 mg of precipitated sodium amoxycillin and 1000 mg of Kollidon PF 12 TM.
  • the sodium amoxycillin disclosed in EP 0012495 is an unstable amorphous material, not the crystalline anhydrous form of sodium amoxycillin disclosed in EP 0131147, and moreover the examples of EP 0012495 include the use of spray dried sodium amoxycillin which is a desiccant per se.
  • a desiccating form of PVP needed to provide adequate desiccation of the pharmaceutical formulation of the invention will again depend upon the components of the formulation and in particular on the nature of the moisture sensitive active material.
  • formulations comprising potassium clavulanate 2200 mg of a 10:1 sodium amoxycillin : potassium clavulanate blend (ratio expressed as weights of free acids equivalent) contained in a sealed vial for injectable administration may be suitably protected by 500 mg or less, e.g 100 mg or less, e.g ca. 30 mg of a desiccating form of PVP.
  • mixturetures of two or more of the above-mentioned classes of desiccants may be used, for example of a desiccating metal salt and a desiccating carbohydrate such as spray dried lactose.
  • the weights of the above mentioned desiccants suggested above to protect the above mentioned weights of sodium amoxycillin : potassium clavulanate blend suggest by extrapolation or interpolation which will be apparent to those skilled in the art suitable weight : weight ratios for protection of other weights of potassium clavulanate by such desiccants.
  • Preferred formulations of the invention are those comprising crystalline sodium amoxycillin, potassium clavulanate and as a desiccant magnesium chloride, sodium chloride or spray-dried lactose. Of these desiccants magnesium chloride is particularly preferred.
  • the method of protecting a moisture sensitive pharmaceutically active material from degradation by moisture provided by this invention is suitable for use in the protection of formulations contained in sealed containers.
  • the formulation may be a formulation which on reconstitution with water yields a solution or suspension which is suitable for administration by injection.
  • Formulations for administration by injection are normally provided in sealed vials, and the present invention therefore also includes sealed vials containing such a formulation.
  • sealed vials When sealing such a formulation into vials it is advisable to take additional physical precautions to reduce the ingress of atmospheric moisture, for example the use of vials made of substantially impermeable materials such as glass, provided with efficient stoppers.
  • the formulation includes potassium clavulanate the formulations are preferably filled in conditions of low relative humidity, typically around 30% RH or lower.
  • the formulations of the invention may also include the excipients which are often included in injectable formulations, for example local anaesthetics, preservatives, buffering agents, surfactants and wetting agents etc.
  • excipients which are often included in injectable formulations, for example local anaesthetics, preservatives, buffering agents, surfactants and wetting agents etc.
  • Such materials, and appropriate quantities in which they may be used, are known in the art, for example for use in injectable potassium clavulanate : sodium amoxycillin co- formulations.
  • such materials may be included in the medium with which the formulations are made up.
  • the formulation may be sterilised in a known way for example with ethylene oxide.
  • individual sterile components of the formulation can be blended in a sterile area.
  • Formulations of the invention may be formulated in any suitable way, for example by simply admixing the dried, powdered or granulated constituents, either prior to introducing them into a vial, or introducing them individually and separately in any order into a vial prior to sealing the vial.
  • potassium clavulanate may be pre-mixed with sodium amoxycillin and then mixed with the desiccant material, and this mixture may then be introduced into a vial prior to sealing the vial.
  • the method of protecting a moisture sensitive pharmaceutically active material contained in sealed containers from degradation by moisture may also be of use in the storage and transportation of such materials, for example by including such a desiccant in bulk pharmaceutically active material, or a mixture comprising it, in a storage and/or transport container.
  • a mixture may be a formulation suitable for administration by injection, or a component of such a formulation.
  • Desiccant materials were prepared by the following procedure:
  • a pharmaceutical formulation comprising a moisture sensitive pharmaceutically active material and a desiccant material, the desiccant being both water soluble and pharmaceutically acceptable by parenteral administration.
  • a pharmaceutical formulation according to claim 1 characterised in that the moisture sensitive pharmaceutically active material is one which is suitable for parenteral administration.
  • a pharmaceutical formulation according to claim 2 characterised in that the moisture sensitive pharmaceutically active material is a pharmaceutically acceptable derivative of clavulanic acid.
  • a pharmaceutical formulation according to claim 3 characterised in that the derivative of clavulanic acid is potassium clavulanate co-formulated with an injectable antibiotic.
  • a pharmaceutical formulation according to claim 4 characterised in that the antibiotic is crystalline sodium amoxycillin.
  • a pharmaceutical formulation according to claim 6 characterised in that the desiccant metal salt is a Group I or Group ⁇ metal chloride or a mixture thereof.
  • a pharmaceutical formulation according to claim 7 characterised in that the desiccating metal salt is a desiccating form of sodium chloride, calcium chloride or magnesium chloride or a mixture theeof.
  • a pharmaceutical formulation according to claim 9 characterised in that the desiccating carbohydrate is selected from lactose, sorbitol, and glucose, in an at

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Biochemistry (AREA)
  • Dermatology (AREA)
  • Inorganic Chemistry (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Formulation pharmaceutique comprenant un principe actif sur le plan pharmacologique, sensible à l'humidité, ainsi qu'un agent de dessiccation à la fois soluble dans l'eau et acceptable sur le plan pharmacologique pour être administré par voie parentérale. Cette formulation convient à une administration parentérale.
PCT/EP1995/002127 1994-06-06 1995-06-02 Formulations injectables contenant un dessiccatif WO1995033487A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP8500355A JPH10500975A (ja) 1994-06-06 1995-06-02 乾燥剤を含有する注射用製剤
EP95922497A EP0764031A1 (fr) 1994-06-06 1995-06-02 Formulations injectables contenant un dessiccatif

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IT94MI001169A ITMI941169A1 (it) 1994-06-06 1994-06-06 Formulazioni farmaceutiche
ITMI94A001169 1994-06-06

Publications (1)

Publication Number Publication Date
WO1995033487A1 true WO1995033487A1 (fr) 1995-12-14

Family

ID=11369056

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1995/002127 WO1995033487A1 (fr) 1994-06-06 1995-06-02 Formulations injectables contenant un dessiccatif

Country Status (4)

Country Link
EP (1) EP0764031A1 (fr)
JP (1) JPH10500975A (fr)
IT (1) ITMI941169A1 (fr)
WO (1) WO1995033487A1 (fr)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000012088A1 (fr) * 1998-08-28 2000-03-09 Smithkline Beecham Plc Formulation pharmaceutique d'amoxycilline de sodium et de clavulanate de potassium
WO2000061115A2 (fr) * 1999-04-13 2000-10-19 Beecham Pharmaceuticals (Pte) Limited Nouvelle methode de traitement
FR2792198A1 (fr) * 1999-04-13 2000-10-20 Beecham Pharm Pte Ltd Formulations pharmaceutiques nouvelles comprenant de l'amoxycilline et du clavulanate de potassium
US6726908B2 (en) 1995-09-07 2004-04-27 Smithkline Beecham P.L.C. Pharmaceutical formulation
US6746692B2 (en) 1999-04-13 2004-06-08 Beecham Pharmaceuticals (Pte) Limited Modified release pharmaceutical formulation comprising amoxycillin
US6756057B2 (en) 2000-10-12 2004-06-29 Beecham Pharmaceuticals (Pte) Limited Amoxicillin and potassium clavulanate dosage form
US6783773B1 (en) 1999-04-13 2004-08-31 Beecham Pharmaceuticals (Pte) Limited Composition comprising amoxicillin and potassium clavulanate
US7011849B2 (en) 2000-10-12 2006-03-14 Beecham Pharmaceuticals (Pte) Limited Second release phase formulation
WO2007093425A2 (fr) * 2006-02-17 2007-08-23 Grünenthal GmbH Forme d'administration par voie orale stable au stockage d'amoxicilline et d'acide clavulanique
EP3773498B1 (fr) 2018-03-29 2022-06-22 Project Pharmaceutics GmbH Formulation pharmaceutique liquide
CN115532234A (zh) * 2022-09-15 2022-12-30 王瑞明 一种新型脱氧干燥剂及其制备方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0008905A1 (fr) * 1978-09-06 1980-03-19 Beecham Group Plc Compositions pharmaceutiques contenant deux dérivés de bêta-lactame
JPS63239237A (ja) * 1986-11-28 1988-10-05 Teisan Seiyaku Kk 乾燥剤含有注射剤
JPS63307824A (ja) * 1987-06-09 1988-12-15 Teisan Seiyaku Kk 安定化注射用粉末製剤

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0008905A1 (fr) * 1978-09-06 1980-03-19 Beecham Group Plc Compositions pharmaceutiques contenant deux dérivés de bêta-lactame
JPS63239237A (ja) * 1986-11-28 1988-10-05 Teisan Seiyaku Kk 乾燥剤含有注射剤
JPS63307824A (ja) * 1987-06-09 1988-12-15 Teisan Seiyaku Kk 安定化注射用粉末製剤

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Section Ch Week 8846, Derwent World Patents Index; Class B07, AN 88-325998 *
PATENT ABSTRACTS OF JAPAN vol. 013, no. 151 (C - 584) 12 April 1989 (1989-04-12) *

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6726908B2 (en) 1995-09-07 2004-04-27 Smithkline Beecham P.L.C. Pharmaceutical formulation
WO2000012088A1 (fr) * 1998-08-28 2000-03-09 Smithkline Beecham Plc Formulation pharmaceutique d'amoxycilline de sodium et de clavulanate de potassium
US7250176B1 (en) 1999-04-13 2007-07-31 Beecham Pharmaceuticals (Pte) Limited Method of treating a bacterial infection
US6783773B1 (en) 1999-04-13 2004-08-31 Beecham Pharmaceuticals (Pte) Limited Composition comprising amoxicillin and potassium clavulanate
WO2000061115A3 (fr) * 1999-04-13 2001-03-01 Beecham Pharm Pte Ltd Nouvelle methode de traitement
GR1003560B (el) * 1999-04-13 2001-03-16 Beecham Pharmaceuticals (Pte) Limited Σκευασματα τροποποιημενης απελευθερωσης αμοξυκιλλινης και κλαβουλανικου καλιου
BE1013309A5 (fr) * 1999-04-13 2001-11-06 Beecham Pharm Pte Ltd Formulations pharmaceutiques nouvelles comprenant l'amoxycilline et du clavulanate de potassium.
US6660299B2 (en) 1999-04-13 2003-12-09 Beecham Pharmaceuticals Limited Modified release pharmaceutical formulation comprising amoxycillin
FR2792198A1 (fr) * 1999-04-13 2000-10-20 Beecham Pharm Pte Ltd Formulations pharmaceutiques nouvelles comprenant de l'amoxycilline et du clavulanate de potassium
US6746692B2 (en) 1999-04-13 2004-06-08 Beecham Pharmaceuticals (Pte) Limited Modified release pharmaceutical formulation comprising amoxycillin
WO2000061115A2 (fr) * 1999-04-13 2000-10-19 Beecham Pharmaceuticals (Pte) Limited Nouvelle methode de traitement
NL1014915C2 (nl) * 1999-04-13 2001-02-12 Beecham Pharm Pte Ltd Nieuwe behandelingsmethode.
US6878386B1 (en) 1999-04-13 2005-04-12 Beecham Pharmaceuticals (Pte) Limited Method of treating a bacterial infection comprising amoxycillin and potassium clavulanate
US7217430B2 (en) 1999-04-13 2007-05-15 Beecham Pharmaceuticals (Pte) Limited Compositions and methods of treatment comprising amoxicillin and potassium clavulanate with xanthan
US7011849B2 (en) 2000-10-12 2006-03-14 Beecham Pharmaceuticals (Pte) Limited Second release phase formulation
US6756057B2 (en) 2000-10-12 2004-06-29 Beecham Pharmaceuticals (Pte) Limited Amoxicillin and potassium clavulanate dosage form
WO2007093425A2 (fr) * 2006-02-17 2007-08-23 Grünenthal GmbH Forme d'administration par voie orale stable au stockage d'amoxicilline et d'acide clavulanique
WO2007093425A3 (fr) * 2006-02-17 2007-10-18 Gruenenthal Gmbh Forme d'administration par voie orale stable au stockage d'amoxicilline et d'acide clavulanique
EP3773498B1 (fr) 2018-03-29 2022-06-22 Project Pharmaceutics GmbH Formulation pharmaceutique liquide
US11752135B2 (en) 2018-03-29 2023-09-12 Project Pharmaceutics Gmbh Liquid pharmaceutical formulation
CN115532234A (zh) * 2022-09-15 2022-12-30 王瑞明 一种新型脱氧干燥剂及其制备方法

Also Published As

Publication number Publication date
ITMI941169A0 (it) 1994-06-06
EP0764031A1 (fr) 1997-03-26
ITMI941169A1 (it) 1995-12-06
JPH10500975A (ja) 1998-01-27

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