ES2545484T3 - Formulación de paracetamol inyectable, estable, lista para usar - Google Patents
Formulación de paracetamol inyectable, estable, lista para usar Download PDFInfo
- Publication number
- ES2545484T3 ES2545484T3 ES09009569.6T ES09009569T ES2545484T3 ES 2545484 T3 ES2545484 T3 ES 2545484T3 ES 09009569 T ES09009569 T ES 09009569T ES 2545484 T3 ES2545484 T3 ES 2545484T3
- Authority
- ES
- Spain
- Prior art keywords
- paracetamol
- stable
- solution
- particulate matter
- formulation
- 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.)
- Active
Links
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 title abstract description 7
- 229960005489 paracetamol Drugs 0.000 title abstract description 7
- 239000000203 mixture Substances 0.000 title description 7
- 238000009472 formulation Methods 0.000 title description 6
- 239000000243 solution Substances 0.000 abstract description 14
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 abstract description 7
- ODLHGICHYURWBS-LKONHMLTSA-N trappsol cyclo Chemical compound CC(O)COC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)COCC(O)C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1COCC(C)O ODLHGICHYURWBS-LKONHMLTSA-N 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract 2
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 238000001802 infusion Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 230000000087 stabilizing effect Effects 0.000 abstract 1
- 239000007857 degradation product Substances 0.000 description 13
- 239000013618 particulate matter Substances 0.000 description 12
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000010902 straw Substances 0.000 description 5
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 239000000654 additive Substances 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000007779 soft material Substances 0.000 description 3
- 229920000858 Cyclodextrin Polymers 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000008215 water for injection Substances 0.000 description 2
- KDQPSPMLNJTZAL-UHFFFAOYSA-L disodium hydrogenphosphate dihydrate Chemical compound O.O.[Na+].[Na+].OP([O-])([O-])=O KDQPSPMLNJTZAL-UHFFFAOYSA-L 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
-
- 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
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
-
- 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
- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
- A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
- A61K47/183—Amino acids, e.g. glycine, EDTA or aspartame
-
- 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
- A61K47/40—Cyclodextrins; Derivatives thereof
-
- 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
- A61K47/69—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 conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6949—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 conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
- A61K47/6951—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 conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes using cyclodextrin
-
- 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
-
- 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
- A61K9/08—Solutions
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nanotechnology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Molecular Biology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Biophysics (AREA)
- Biotechnology (AREA)
- Medical Informatics (AREA)
- General Engineering & Computer Science (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Inorganic Chemistry (AREA)
- Dermatology (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Una solución de paracetamol acuosa estable para uso en infusión IV que comprende una 2-hidroxipropil-betaciclodextrina como un compuesto estabilizante-disolvente en donde la relación molar de paracetamol a 2-hidroxipropil-beta-ciclodextrina es de 100:1 a 0,1:1, y la solución acuosa comprende de 2 mg a 200 mg de paracetamol por ml de solución, comprendiendo además AEDT y monotioglicerol como compuestos estabilizantes, en donde la concentración de AEDT es de 0,0015 a 1 mg por ml de solución y la concentración de monotioglicerol es de 0,015 a 1 mg por ml de solución.
Description
- Ingrediente
- Cantidad/100 ml
- Agua para inyección, hasta
- 100 ml
- pH final (HCl o NaOH) 1M
- 5,5-6,5
En la Tabla 2 a continuación se proporciona la composición unitaria de una segunda formulación (testigo, sin aditivos):
Tabla 2
- Ingrediente
- Cantidad/100 ml
- Paracetamol
- 1.000 mg
- Hidroxipropil-β-ciclodextrina
- 666 mg
- NaCl
- 600 mg
- Fosfato disódico dihidrato
- 35,6 mg
- Agua para inyección, hasta
- 100 ml
- pH final (HCl o NaOH) 1M
- 5,5-6,5
Se fabricaron formulaciones a escala de laboratorio dadas en los Ejemplos 1 y 2 de la presente invención y se envasaron en viales de vidrio transparente y material polímero (bolsas de material blando) y se incluyeron en un programa de estabilidad. Las Tablas 3 - 6 a continuación resumen los resultados obtenidos:
10 Tabla 3
- Estabilidad de lotes de (Paracetamol - HPBCD) de 1.000 mg/100 ml a 40°C durante 3 meses
- Antioxidante
- Estabilidad química pH Aspecto Comentarios
- Testigo (sin aditivos)
- Nivel aceptable de producto de degradación conocido Descendente Aparición de color; inestabilidad física No estable (se continúa hasta los 6 meses como testigo)
- AEDT 10 mg
- Nivel aceptable de producto de degradación conocido Ligeramente descendente Estable Cumple, se continúa la evaluación
- NAC 10 mg + AEDT 5 mg
- Nivel aceptable de producto de degradación conocido Descendente Aparición de color; inestabilidad física No estable, se continúa la evaluación
- Monotioglicerol 20 mg
- Nivel aceptable de producto de degradación conocido Estable Estable Cumple, se continúa la evaluación
Tabla 4Tabla 5Tabla 6
- Estabilidad de lotes de (Paracetamol - HPBCD) de 1.000 mg/100 ml a 40°C durante 3 meses
- Antioxidante
- Estabilidad química pH Aspecto Comentarios
- Testigo (sin aditivos)
- Nivel aceptable de producto de degradación conocido Ligeramente descendente Aparición de color; inestabilidad física No estable (testigo)
- AEDT 10 mg
- Nivel aceptable de producto de degradación conocido Ligeramente descendente Transparente, color pajizo.Libre de materia en partículas visible Formulaciónposible
- NAC 10 mg + AEDT 5 mg
- Nivel aceptable de producto de degradación conocido Descendente Aparición de color; inestabilidad física No estable
- Monotioglicerol 20 mg
- Nivel aceptable de producto de degradación conocido Ligeramente descendente Transparente, color pajizo.Libre de materia en partículas visible Formulaciónposible
- Monotioglicerol 10 mg +AEDT 10 mg
- Nivel aceptable de producto de degradación conocido Estable Transparente, color pajizo.Libre de materia en partículas visible Formulaciónposible
- DATOS DE ESTABILIDAD PARA SOLUCIONES de Paracetamol-_HPB 1.000 mg/100 ml (T = 6 meses) bolsas de material blando, viales de vidrio transparente
- Estabilizado con: soluciones testigo
- Estabilizado con: 10 mg de AEDT + 10 mg de monotioglicerol
- 25ºC
- 40ºC 25ºC 40ºC
- Aspecto
- Solución transparente incolora Aparición de color; inestabilidad física Aspecto Solución transparente incolora Solución transparente de color pajizo
- pH
- 6 5,7 pH 6 5,9
- Materia enpartículas
- Libre de materia en partículas visible Libre de materia en partículas visible Materia enpartículas Libre de materia en partículas visible Libre de materia en partículas visible
- Valoración (HPLC) (% de T=0)
- 100,1 98 Valoración (HPLC) (% de T=0) 100 99,5
- % de p-aminofenol
- <0,005 m/m 0,5 % de p-aminofenol <0,005 m/m 0,02
- Otros productos de degradación
- Ninguno detectado Ninguno detectado Otros productos de degradación Ninguno detectado Ninguno detectado
- DATOS DE ESTABILIDAD PARA SOLUCIONES de Paracetamol-_HPB 1.000 mg/100 ml (T = 6 meses) bolsas de material blando
- Estabilizado con: soluciones testigo
- Estabilizado con: 10 mg de AEDT + 10 mg de monotioglicerol
- 25ºC
- 40ºC 25ºC 40ºC
- Aspecto
- Solución transparente incolora Aparición de color; inestabilidad física Aspecto Solución transparente incolora Solución transparente de color pajizo
- pH
- 6 5,4 pH 6 5,8
- Materia en partículas
- Libre de materia en partículas visible Libre de materia en partículas visible Materia enpartículas Libre de materia en partículas visible Libre de materia en partículas visible
- Valoración (HPLC) (% de T=0)
- 99,7 97,5 Valoración (HPLC) (% de T=0) 100 99,3
- % de p-aminofenol
- <0,005 m/m 0,8 % de p-aminofenol <0,005 m/m 0,03
- Otros productos de degradación
- Ninguno detectado Ninguno detectado Otros productos de degradación Ninguno detectado Ninguno detectado
Claims (1)
-
imagen1
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09009569.6A EP2277546B1 (en) | 2009-07-23 | 2009-07-23 | Stable ready to use injectable paracetamol formulation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2545484T3 true ES2545484T3 (es) | 2015-09-11 |
Family
ID=41264251
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES09009569.6T Active ES2545484T3 (es) | 2009-07-23 | 2009-07-23 | Formulación de paracetamol inyectable, estable, lista para usar |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP2277546B1 (es) |
| CY (1) | CY1116746T1 (es) |
| DK (1) | DK2277546T3 (es) |
| ES (1) | ES2545484T3 (es) |
| HK (1) | HK1153400A1 (es) |
| HR (1) | HRP20150815T1 (es) |
| HU (1) | HUE027032T2 (es) |
| PL (1) | PL2277546T3 (es) |
| PT (1) | PT2277546E (es) |
| SI (1) | SI2277546T1 (es) |
| SM (1) | SMT201500192B (es) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2414557B1 (es) | 2012-01-16 | 2014-06-10 | Novocat Farma, S.A. | Composición acuosa de paracetamol para inyección |
| ZA201300398B (en) * | 2012-11-27 | 2013-09-25 | Genfarma Laboratories S L | Injectable liquid formulation of the combination of tramadol and paracetamol |
| AU2017326519B2 (en) * | 2016-09-16 | 2023-03-16 | Cydex Pharmaceuticals, Inc. | Formulations containing acetaminophen and sulfoalkyl ether cyclodextrin |
| GR1010637B (el) * | 2023-01-13 | 2024-02-15 | Ιουλια Κλεωνος Τσετη | Σταθερο υδατικο διαλυμα παρακεταμολης για χρηση σε ενδοφλεβια εγχυση |
| WO2024246565A2 (en) | 2023-06-02 | 2024-12-05 | Ioulia Tseti | Pharmaceutical composition comprising ibuprofen |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4727064A (en) * | 1984-04-25 | 1988-02-23 | The United States Of America As Represented By The Department Of Health And Human Services | Pharmaceutical preparations containing cyclodextrin derivatives |
| FR2751875B1 (fr) * | 1996-08-05 | 1998-12-24 | Scr Newpharm | Nouvelles formulations liquides stables a base de paracetamol et leur mode de preparation |
| SK2822004A3 (sk) * | 2001-12-18 | 2005-01-03 | Uni-Pharma Kleon Tsetis Pharmaceutical Laboratories S.A. | Parenterálny prípravok obsahujúci paracetamol |
| CN1232539C (zh) * | 2002-05-10 | 2005-12-21 | 刘云清 | 有机药物与倍他环糊精衍生物的配合物及其制备方法 |
| CA2661193A1 (en) * | 2006-08-08 | 2008-02-21 | Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College | Therapeutic methods for neuropathic pain |
| JP5909750B2 (ja) * | 2007-11-13 | 2016-04-27 | マリンクロット アイピー | 低用量静脈内アセトアミノフェン |
-
2009
- 2009-07-23 DK DK09009569.6T patent/DK2277546T3/en active
- 2009-07-23 PL PL09009569T patent/PL2277546T3/pl unknown
- 2009-07-23 PT PT90095696T patent/PT2277546E/pt unknown
- 2009-07-23 SI SI200931237T patent/SI2277546T1/sl unknown
- 2009-07-23 HU HUE09009569A patent/HUE027032T2/en unknown
- 2009-07-23 ES ES09009569.6T patent/ES2545484T3/es active Active
- 2009-07-23 EP EP09009569.6A patent/EP2277546B1/en active Active
-
2011
- 2011-07-22 HK HK11107648.8A patent/HK1153400A1/xx not_active IP Right Cessation
-
2015
- 2015-07-27 HR HRP20150815TT patent/HRP20150815T1/hr unknown
- 2015-08-06 SM SM201500192T patent/SMT201500192B/xx unknown
- 2015-08-21 CY CY20151100733T patent/CY1116746T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PT2277546E (pt) | 2015-09-25 |
| EP2277546A1 (en) | 2011-01-26 |
| HUE027032T2 (en) | 2016-08-29 |
| SI2277546T1 (sl) | 2015-09-30 |
| HRP20150815T1 (hr) | 2015-09-11 |
| HK1153400A1 (en) | 2012-03-30 |
| CY1116746T1 (el) | 2017-03-15 |
| DK2277546T3 (en) | 2015-08-17 |
| EP2277546B1 (en) | 2015-07-15 |
| PL2277546T3 (pl) | 2015-10-30 |
| SMT201500192B (it) | 2015-09-07 |
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