AP536A - Oral liquid compositions containing paroxetine resinate - Google Patents

Oral liquid compositions containing paroxetine resinate Download PDF

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Publication number
AP536A
AP536A APAP/P/1995/000715A AP9500715A AP536A AP 536 A AP536 A AP 536A AP 9500715 A AP9500715 A AP 9500715A AP 536 A AP536 A AP 536A
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AP
ARIPO
Prior art keywords
paroxetine
pharmaceutical composition
oral liquid
depression
composition according
Prior art date
Application number
APAP/P/1995/000715A
Other versions
AP9500715A0 (en
Inventor
Graham Stanley Leonard
David Cooper
Original Assignee
Smithkline Beecham Plc
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 Plc filed Critical Smithkline Beecham Plc
Publication of AP9500715A0 publication Critical patent/AP9500715A0/en
Application granted granted Critical
Publication of AP536A publication Critical patent/AP536A/en

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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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/4525—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with oxygen as a ring hetero atom
    • 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
    • A61K47/50—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/56—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
    • A61K47/58—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. poly[meth]acrylate, polyacrylamide, polystyrene, polyvinylpyrrolidone, polyvinylalcohol or polystyrene sulfonic acid resin
    • A61K47/585—Ion exchange resins, e.g. polystyrene sulfonic acid resin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/26—Psychostimulants, e.g. nicotine, cocaine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents

Abstract

A palatable and bioavailable oral liquid formulation comprising a paroxetine-ion exchange resinate complex,methods of preparation and use as a pharmaceutical

Description

NOVEL FORMULATION
The present invention relates to novel formulations and to the use of such a formulation in the treatment and/or prevention of certain disorders.
US Patent 4,007,196 describes certain compounds which possess antidepressant activity. One specific compound mentioned in this patent is known as paroxetine and which has the following formula:
F
H
This compound has been approved for human use and is being sold in many countries around the world as an anti-depressant agent
All paroxetine sold to date has been in the form of oral swallow tablets.
Many physicians have expressed a desire to be able to prescribe an oral liquid containing paroxetine and some have even made their own oral liquid by crushing conventional swallow tablets and mixing them with water. There are however, a number of draw-backs to this oral liquid, firstly paroxetine has a very bitter taste which is highly noticeable when administered as an oral liquid, secondly such oral liquids have poor stability qualities and have a shelf-life of only a few days.
WO 91/13612 relates to the sustained release of pharmaceuticals using compositions in which the drug is complexed with an ion-exchange resin. The specific ion-exchange resin described in this published patent application is Amberlite IRP-69.
When Amberlite IRP-69 is used to complex with paroxetine it was found that whilst the taste was effectively masked the composition had an unacceptably low bioavailability when compared to a swallow tablet.
It has now been found that Amberlite IRP-88 can be used to form a stable taste masted complex with paroxetine and which complex has acceptable bioavailability when compared to the conventional swallow tablet.
Accordingly, the present invention provides an oral liquid pharmaceutical composition comprising a paroxetine - Amberlite IRP-88 complex.
Amberlite IRP-88 is commercially available from Rohm & Haas in a pharmaceutically acceptable grade.------c~ c
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The oral liquid pharmaceutical composition is prepared in conventional manner such as by mixing paroxetine and Amberlite IRP-88 together in an aqueous medium. Suitably the IRP-88 and paroxetine are present in a ratio of 1:1 to 2:1. It should be appreciated that superior taste masking properties are obtained with a 2:1 ratio.
Other pharmaceutically acceptable excipients may also be added such as thickeners such as Keltrol and/or Avicel (in particular Avicel CL 611); dispersants such as propylene glycol; moisture retaining agents such as glycerol; sweetners such as sorbitol and sodium saccharin buffering agents such as citric acid and sodium citrate; preservatives such as sodium benzoate and mixtures of methyl and and propyl parabens (parahydroxybenzoates), artificial colours such as F D and C Yellow No. 6 Sunset Yellow; flavouring such as Givaudan Natural Orange and/or Lemon; and antifoaming agents such as silicone anti-foam.
Preferably the amounts of buffering agents are controlled to give a pH of 4 to 6. Most preferably a pH of 4.5 to 6.0.
The amount of paroxetine used is adjusted such that in a single unit dose there is a therapeutically effective amount of paroxetine. Preferably the unit dose contains from 10 to 100 mg paroxetine (as measured in terms of the free base). More preferable the amount of paroxetine in a unit dose is lOmg, 20mg, 30mg, 40mg or
50mg. The most prefened amount of paroxetine in a unit dose is 20mg of paroxetine.
Preferably the volume of liquid in a unit dose is in the range 5 to 20ml most preferably 10ml.
Preferably paroxetine used in the formulation is in the form of the hydrocholide hemi-hydrate which may be prepared according to the procedures outlined in US Patent 4,721,723.
Suitable procedures for preparing paroxetine include those mentioned in US
Patents 4,009,196,4,902,801,4,861,893 and 5,039,803 and PCT/GB 93/00721.
It has been mentioned that paroxetine has particular utility in the treatment of depression, paroxetine may also be used in the treatment of mixed anxiety and depression, obsessive compulsive disorders, panic, pain, obesity, senile dementia, migraine, bulimia, anorexia, social phobia and the depression arising from premenstrual tension and adolescence.
The present invention therefore also provides a method of treating or preventing any of the above disorders which comprises administering an effective or prophylatic amount of an oral liquid pharmaceutical composition comprising a paroxetine-Amberlite IRP-88 complex to a sufferer in need thereof.
The present invention further provides the use of an oral liquid pharmaceutical composition comprising a paroxetine-Amberlite IRP-88 complex in the manufacture of a medicament for treating or preventing the above disorders.>
.
cc
C’ c
cr
AP.00536
The present invention yet further provides a pharmaceutical composition for use in the treatment or prevention of the above disorders which comprises a paroxetine-Amberlite IRP-88 complex admixed with a pharmaceutically acceptable carrier.
The following examples illustrate the present invention:
Example 1 (1:1) Ratio of Amberlite IRP-88 to paroxetine.
• mg/10 ml
Paroxetine hydrochloride t 22.8
Amberlite IRP 88 (< 63 pm) 22.8
Keltrol 40.0
Propylene Glycol 350.0
Glycerol 350.0
Sorbitol (70%) 4000.0
Citric acid 15.0
Sodium Citrate 10.0
Sodium benzoate 10.0
Sodium Saccharin 5.0
Sunset Yellow 0.5
Givaudan Natural Orange 1.0
Givaudan Natural Lemon 2.0
Antifoam Silicone 20.0
Water to 10.0 ·
AP/Γ.' 9 5 / 0 0 7 1 5
Example 2 (2:1) Ratio of Amberlite IRP to paroxetine mg/lOml
Paroxetine hydrochloride (< 180 microns) Amberlite IRP 88 (< 200 mesh)
Avicel CL 611
Propylene Glycol
Glycerol
Sorbitol (70%)
Citric acid (anhydrous)
22.8
40.0*
300.0
500.0
500.0
4000.0
15.0
BAD ORIGINAL £
Sodium Citrate (dihydrate) 10.0
Methyl parahydroxybenzoate 20.0
Propyl parahydroxybenzoate 6.0
Sodium Saccharin 5.0
FD&C Yellow No. 6 0.9
Givaudan Natural Orange 74388-74 1.0 mcl
Givaudan Natural Lemon74940-74 2.0 mcl
Silicone Antifoam 1510 20.0
Water to 10.0 ♦ on an Anhydrous basis
Example 3 5
As above but 40.0 mg was replaced with 300 mg of Avicel CL 611.
Example 4
As above but 15 mg of Keltrol and 300 mg of Avicel CL 611 was used.--

Claims (4)

  1. Ciaimc
    AP. Ο Ο 5 3 6
    1. An oral liquid composition for sustained release of a pharmaceutical acceptable drug comprising a drug-resin composition tormed from a pharmaceutical active drug and an ion-exchange resin in which at least 30% by weight of resinate particles having a particle size below 35 pm characterized that the active drug is paroxetine.
    5.
    6.
    7.
    I
    C 8.
    9.
  2. 2. A process for preparing a pharmaceutical composition as defined in claim 1 which process comprises mixing paroxetine and Amberlite IRP-88 together in aqueous medium.
  3. 3. A process according to claim 2 in which the molar ratio of IRP 88 to paroxetine is 1:1 to 2:1.
  4. 4. A pharmaceutical composition according to claim 1 in which any one or more of the following is added; thickeners, dispersants, moisture retaining agents, sweeteners, buffering agents, preservatives, artificial colours, flavourings and anti-foaming agents.
    A pharmaceutical composition according to claim 4 in which the amount of buffering agents are controlled to give a pH of 4 to 6.
    A pharmaceutical composition according to any one of claims 1,4 or 5 which is in the form of a unit dose. , ;
    C 3*1
    A pharmaceutical composition according to claim 6 in which the amount of paroxetine in the unit dose is lOmg, 20mg, 30mg, 40mg, or 50mg.
    OA pharmaceutical composition according to claims 1 or 4 to 7 in which the paroxetine is in the form of the hydrochloride hemihydrate.
    A method of treating or preventing mixed anxiety and depression, obsessive compulsive disorders, panic, pain, obesity, senile dementia, migraine, bulimia, anorexia, social phobia and depression arising from pre-menstrual tension and adolescence which comprises administering an effective or prophylatic amount of an oral liquid pharmaceutical composition as defined in claim 1. According to any one of claims 1 and 4 to 8 to a sufferer in need thereof.
    10. The use of an oral liquid pharmaceutical composition as defined in claim 1 comprising a paroxetine-Amberlite IRP-88 complex in the manufacture of medicament for treating or preventing mixed anxiety and depression, obsessive
    BAD ORIGINAL compulsive disorders, panic, pain, obesity, senile dementia, migraine, bulimia, anorexia, social phobia and depression arising from pre-menstrual tension and adolescence.
    11. A pharmaceutical composition as defined in claim 1 for use in the treatment or 5 prevention of anxiety and depression, obsessive compulsive disorders, panic, pain, obesity, senile dementia, migraine, bulimia, anorexia, social phobia and depression arising from pre-menstrual tension and adolescence.
    Dated this 1st Day of February 1995. ’ ''—·
    MONEY - TT- TKENBERG <O
    O
    -6BAD ORIGINAL
    AP.00536
    ABS'ihACT
    A palatable and bioavaiiable oral liquid formulation comprising a paroxetine-ion exchange resinate complex, methods of preparation and use as a pharmaceutical.
    s I L 0 0 / 5 6 /d/dV
APAP/P/1995/000715A 1994-02-03 1995-02-01 Oral liquid compositions containing paroxetine resinate AP536A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB9402029A GB9402029D0 (en) 1994-02-03 1994-02-03 Novel formulation

Publications (2)

Publication Number Publication Date
AP9500715A0 AP9500715A0 (en) 1995-04-30
AP536A true AP536A (en) 1996-09-26

Family

ID=10749765

Family Applications (2)

Application Number Title Priority Date Filing Date
APAP/P/1996/000839A AP611A (en) 1994-02-03 1995-01-30 Oral liquid compositions containing paroxetine resinate.
APAP/P/1995/000715A AP536A (en) 1994-02-03 1995-02-01 Oral liquid compositions containing paroxetine resinate

Family Applications Before (1)

Application Number Title Priority Date Filing Date
APAP/P/1996/000839A AP611A (en) 1994-02-03 1995-01-30 Oral liquid compositions containing paroxetine resinate.

Country Status (34)

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US (1) US5811436A (en)
EP (1) EP0742715B1 (en)
JP (1) JP4445590B2 (en)
CN (1) CN1074922C (en)
AP (2) AP611A (en)
AT (1) ATE178489T1 (en)
AU (1) AU682091B2 (en)
BG (1) BG62843B1 (en)
BR (1) BR9507055A (en)
CA (1) CA2182593A1 (en)
CZ (1) CZ285128B6 (en)
DE (1) DE69508924T2 (en)
DK (1) DK0742715T3 (en)
DZ (1) DZ1850A1 (en)
ES (1) ES2129806T3 (en)
FI (1) FI118205B (en)
GB (1) GB9402029D0 (en)
GR (1) GR3030131T3 (en)
HK (1) HK1012288A1 (en)
HU (1) HUT75941A (en)
IL (1) IL112521A (en)
MA (1) MA23441A1 (en)
MX (1) MX9603203A (en)
MY (1) MY113036A (en)
NO (1) NO307954B1 (en)
NZ (1) NZ278891A (en)
OA (1) OA10446A (en)
PL (1) PL178331B1 (en)
RO (1) RO116342B1 (en)
RU (1) RU2136281C1 (en)
SK (1) SK281214B6 (en)
TW (1) TW436296B (en)
WO (1) WO1995020964A1 (en)
ZA (1) ZA95776B (en)

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US6660298B1 (en) * 2000-07-27 2003-12-09 Pentech Pharmaceuticals, Inc. Paroxetine tablets and capsules
US6720003B2 (en) * 2001-02-16 2004-04-13 Andrx Corporation Serotonin reuptake inhibitor formulations
US20020176842A1 (en) * 2001-04-09 2002-11-28 Lyn Hughes Extended release of active ingredients
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US6906206B2 (en) * 2001-04-30 2005-06-14 Wyeth Antidepressant azaheterocyclylmethyl derivatives of 1,4,5-trioxa-phenanthrene
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US20100273822A1 (en) * 2009-04-22 2010-10-28 William Wayne Howard Immediate release compositions and methods for delivering drug formulations using strong acid ion exchange resins
US8758779B2 (en) 2009-06-25 2014-06-24 Wockhardt Ltd. Pharmaceutical composition of duloxetine
US8187617B2 (en) * 2009-09-11 2012-05-29 William Wayne Howard Immediate release compositions and methods for delivering drug formulations using weak acid ion exchange resins in abnormally high pH environments
JP5831449B2 (en) 2010-05-19 2015-12-09 アステラス製薬株式会社 Solifenacin-containing pharmaceutical composition
CN104027306A (en) * 2014-06-25 2014-09-10 万特制药(海南)有限公司 Paroxetine oral suspension and preparation method thereof
GB201419261D0 (en) * 2014-10-29 2014-12-10 Therakind Ltd Formulations
CN104382870A (en) * 2014-10-30 2015-03-04 万全万特制药江苏有限公司 Compound containing polacrilin potassium-paroxetine
CN106309363A (en) * 2016-09-24 2017-01-11 万特制药(海南)有限公司 Paroxetine hydrochloride oral suspension and preparation method thereof
CN108926528A (en) * 2017-05-25 2018-12-04 北京万全德众医药生物技术有限公司 Liquid oral compositions containing Amisulpride resinate
EP3917523A4 (en) 2019-02-01 2022-10-19 University of South Carolina Bicyclic pyridine compositions and methods of using the same for cancer therapy
CN113209017B (en) * 2021-06-02 2023-06-20 上海美优制药有限公司 Paroxetine hydrochloride suspension and preparation method thereof
GB202212116D0 (en) 2022-08-19 2022-10-05 Beckley Psytech Ltd Pharmaceutically acceptable salts and Compositions thereof

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WO1991013612A1 (en) * 1990-03-12 1991-09-19 Beecham Group Plc Composition

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CZ229396A3 (en) 1997-01-15
NO963244D0 (en) 1996-08-02
JPH09508402A (en) 1997-08-26
IL112521A (en) 1999-09-22
WO1995020964A1 (en) 1995-08-10
FI963051A0 (en) 1996-08-01
EP0742715B1 (en) 1999-04-07
CZ285128B6 (en) 1999-05-12
BR9507055A (en) 1997-09-02
ATE178489T1 (en) 1999-04-15
CN1074922C (en) 2001-11-21
HUT75941A (en) 1997-05-28
GR3030131T3 (en) 1999-07-30
TW436296B (en) 2001-05-28
SK281214B6 (en) 2001-01-18
AU682091B2 (en) 1997-09-18
DE69508924T2 (en) 1999-10-21
CA2182593A1 (en) 1995-08-10
AP9600839A0 (en) 1996-07-31
NO307954B1 (en) 2000-06-26
JP4445590B2 (en) 2010-04-07
ES2129806T3 (en) 1999-06-16
BG62843B1 (en) 2000-09-29
NO963244L (en) 1996-08-02
AP9500715A0 (en) 1995-04-30
BG100763A (en) 1997-03-31
DK0742715T3 (en) 1999-10-18
MA23441A1 (en) 1995-10-01
GB9402029D0 (en) 1994-03-30
FI118205B (en) 2007-08-31
PL315679A1 (en) 1996-11-25
DZ1850A1 (en) 2002-02-17
ZA95776B (en) 1996-08-01
PL178331B1 (en) 2000-04-28
IL112521A0 (en) 1995-05-26
NZ278891A (en) 1998-01-26
HU9602151D0 (en) 1996-09-30
MY113036A (en) 2001-11-30
EP0742715A1 (en) 1996-11-20
CN1140411A (en) 1997-01-15
OA10446A (en) 2002-03-26
DE69508924D1 (en) 1999-05-12
US5811436A (en) 1998-09-22
AP611A (en) 1997-09-03
FI963051A (en) 1996-08-01
HK1012288A1 (en) 1999-07-30
SK100496A3 (en) 1996-12-04
AU1536895A (en) 1995-08-21
RO116342B1 (en) 2001-01-30
RU2136281C1 (en) 1999-09-10
MX9603203A (en) 1997-03-29

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