ES2581212T3 - Administración mejorada de tetahidrocannabinol - Google Patents

Administración mejorada de tetahidrocannabinol Download PDF

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ES2581212T3
ES2581212T3 ES06827524.7T ES06827524T ES2581212T3 ES 2581212 T3 ES2581212 T3 ES 2581212T3 ES 06827524 T ES06827524 T ES 06827524T ES 2581212 T3 ES2581212 T3 ES 2581212T3
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tetrahydrocannabinol
sedds
weight
cannabidiol
amg
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Ram B. Murty
Santos B. Murty
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Murty Pharmaceuticals Inc
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    • 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
    • A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
    • 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
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
    • 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
    • A61K31/655—Azo (—N=N—), diazo (=N2), azoxy (>N—O—N< or N(=O)—N<), azido (—N3) or diazoamino (—N=N—N<) compounds
    • 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
    • A61K31/658—Medicinal preparations containing organic active ingredients o-phenolic cannabinoids, e.g. cannabidiol, cannabigerolic acid, cannabichromene or tetrahydrocannabinol
    • 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
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/12—Carboxylic acids; Salts or anhydrides 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
    • A61K47/06—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
    • A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
    • 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
    • A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
    • 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
    • A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
    • 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
    • A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
    • 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
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/4841—Filling excipients; Inactive ingredients
    • A61K9/4858—Organic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
    • 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

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
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  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Dispersion Chemistry (AREA)
  • Pain & Pain Management (AREA)
  • Hospice & Palliative Care (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Otolaryngology (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Forma de dosificación oral de cannabinoides que comprende del 1 al 60% en peso de una forma farmacológicamente activa de cannabinoides en un sistema autoemulsionante que comprende del 20 al 80% en peso de medio oleoso, del 10 al 60% en peso de tensioactivo, seleccionándose el cannabinoide farmacológicamente activo del grupo que consiste en tetrahidrocannabinol, D9-tetrahidrocannabinol, D8-tetrahidrocannabinol, D8- tetrahidrocannabinol-DMH, análogo propílico del D9-tetrahidrocannabinol, 11-hidroxi-tetrahidrocannabinol, 11-nor-9- carboxi-tetrahidrocannabinol, 5'-azido-D8-tetrahidrocannabinol, AMG-1, AMG-3, AM411, AM708, AM836, AM855, AM919, AM926, AM938, cannabidiol, análogo propílico del cannabidiol, cannabinol, cannabicromeno, análogo propílico del cannabicromeno, cannabigerol, CP 47497, CP 55940, CP 55244, CP 50556, CT-3, dimetilheptil HHC, HU-210, HU-211, HU-308, WIN 55212-2, desacetil-L-nantradol, dexanabinol, JWH-051, levonantradol, L-759633, nabilona, O-1184, y mezclas de los mismos; y el medio oleoso se selecciona del grupo que consiste en triglicéridos y/o glicéridos mixtos y/o ácidos grasos libres que tienen de C6 a C32 átomos de carbono.

Description

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TABLA 1
Composición
mg de ingrediente por formulación (% por cápsula)
(i)
(ii) (iii) (iv) (v) (vi) 5(vii)
Δ9-THC (en forma de resina)
10 (3,85) 10 (3,85) 10 (3,85) 10 (3,85) 10 (3,65) 10 (3,71) 10 (4,1)
Ácido oleico
- 125 (48,1) 125 (48,1) 62 (24) - 235 (95,95)
Capmul MCM (L)
250 (96,15) - - - - 10 -
Labrasol
- 125 (48,1) - - - 131,5 (48,88) -
Labrafil M 1944CS
- - 125 (48,1) 188 (72,16) 139 (50,70) 15 -
Aceite de sésamo
- - - - 125 (45,65) -
Aceite de soja
- - - - - 127,5 (47,41) -
Total
260 (100) 260 (100) 260 (100) 260 (100) 274 (100) 269 (100) 20 245 (100)
[0088] La Figura 1 muestra que las formulaciones ensayadas demostraron ser más óptimas que las formulaciones comerciales. Estos estudios de disolución se llevaron a cabo utilizando SLS al 2% en medios acuosos (aparato de paleta, 75 rpm). Estas pruebas también establecieron que era posible mejorar la disolución de THC utilizando sistemas de administración de fármacos autoemulsionantes.
Ejemplo 2
[0089] La formulación preparada anteriormente vii (Tabla 1), que se clasificó como sistema SEDDS de tipo I, se evaluó en varios medios de disolución a 37ºC (paleta, 75 rpm) con el fin de determinar las condiciones de ensayo más adecuadas. El porcentaje de liberación obtenido en cada uno de los medio de disolución ensayados se expone en la Tabla 2.
TABLA 2
Medio de disolución
Porcentaje de liberación (min)
15
30 60 120 240
Agua
0 0 0 0,3 1,1
SLS al 2% en Agua
≥100,0 ≥100,0 ≥100,0 ≥100,0 ≥100,0
Triton X-100 al 5%
67,5 ≥100,0 ≥100,0 ≥100,0 ≥100,0
Tampón de acetato, pH 4,5
0,0 0,0 0,0 0,0, 0,0,
Tampón de borato, pH 9,5
39,8 67,3 ≥100,0 ≥100,0 ≥100,0
HCl 0,1N
0,0 0,0 0,0, 0,0, 0,0,
Es evidente a partir de los resultados anteriores en la tabla 2 que SLS al 2% o Triton X-100 al 5% es una elección ideal para evaluar formulaciones SEDDS de THC. Pueden ser necesarios medios adicionales, tales como medios gástricos e intestinales simulados para una evaluación adicional. En particular, se utilizan preferiblemente medios intestinales simulados de estado de ayuno (FaSSIF) y medios intestinales simulados de estado de alimentación (FeSSIF).
[0090] Los datos en la Tabla 2 también establece que los sistemas SEDDS tienen un efecto protector para Δ-9 THC frente a la degradación catalizada por ácido en el medio del estómago. Esto es debido al hecho de que el fármaco es retenido dentro de la matriz SEDDS tras la dilución inicial en medios acuosos y no está disponible para su liberación en el medio circundante. Tras realizar las pruebas de dilución acuosa para formulaciones de placebo descritas a continuación (Ejemplos 3 y 4), la formación de dispersiones sólidas de partícula gruesa o dispersiones turbias muestran además que los sistemas SEDDS protegen los cannabinoides activos frente a la degradación catalizada por ácido en el estómago (Ejemplo 5).
Ejemplo 3
[0091] Los sistemas SEDDS Tipo I, Tipo II y Tipo III preferidos son de naturaleza isotrópica con un comportamiento de fase uniforme antes de la dilución en medio acuoso. Las fórmulas de SEDDS separadas en fases no son de naturaleza isotrópica y muestran agrietamiento o mala uniformidad de matriz en el caso de semisólidos.
[0092] La Tabla 3 a continuación muestra los resultados de los exámenes de comportamiento de fase para seleccionar SEDDS, formulaciones de placebo que utilizan combinaciones de un medio portador oleoso con Cremophor EL. Los exámenes fueron macroscópicos (es decir, visuales), así como microscópicos (Olympus®
12
Stereomicroscope).
TABLA 3
Ingrediente
(a) mg (%) (b) mg (%) (c) mg (%) (d) mg (%)
ESTADO FÍSICO
Líquido Líquido Semisólido fluido Semisólido
Agente activo
0 (3,85) 0 (3,85) 0 (3,85) 0 (3,85)
Componente de Aceite/ Portador de Ácido Graso (por ejemplo Ácido Oleico)
120,0 (46,15) 121,75 (46,8) 158,0 (60,8) 112,5 (43,1)
Componente de Tensioactivo (por ejemplo Cremóforo EL)
120,0 (46,15) 121,75 (46,8) 79,0 (30,4) 112,5 (43,1)
Vitamina E, FCC
5,0 (1,925) - - -
Palmitato de ascorbilo
5,0 (1,925) 6,5 (2,5) 13,0 (5,0) 26,0 (10,0)
Total*
250 (100) 250 (100) 250 (100) 251 (100)
*Porcentajes en “()”se basan en el peso de llenado de ∼260 mg para todas las formulaciones cargadas de fármaco
5
[0093] La Tabla 3 muestra que con el aumento de las concentraciones de palmitato de ascorbilo, la matriz SEDDS cambia de estado líquido a un estado semisólido o estado semisólido fluido. Por lo tanto, el palmitato de ascorbilo, un soluto anfifílico, sirve como un inductor de semisólido cuando está presente en concentraciones en exceso en la matriz de formulación SEDDS.
10 [0094] En el presente ejemplo, el medio portador oleoso se sustituye por varios "aceites". El componente tensioactivo se sustituye por diversos ingredientes. Los ingredientes adicionales en la matriz SEDDS incluyen modificadores de la viscosidad, antioxidantes, e inhibidores metabólicos/PGP. Cuando las matrices SEDDS se administran con o sin una cubierta de cápsula a un sistema gastrointestinal de mamíferos (véase el Ejemplo 5), se
15 aplica lo siguiente:
(i)
La dispersión acuosa inicial de los sistemas SEDDS en los contenidos ácidos del estómago da lugar a una dispersión de partícula gruesa o dispersión sólida para la protección frente al medio ácido.
(ii)
Con la presencia de sales biliares en el duodeno superior, la forma de dosificación SEDDS se incorpora en las vías de absorción de los lípidos de mamíferos, evitando así el metabolismo hepático de primer paso.
20 (iii) Cuando se comparan las composiciones SEDDS líquidas frente a las composiciones SEDDS semisólidas debido a una mayor concentración de anfifílico/no anfifilico, el primer sistema proporciona perfiles de disolución del fármaco más rápidos, mientras que el segundo sistema proporciona perfiles de disolución más prolongados, respectivamente.
(iv) Los sistemas SEDDS líquidos de liberan de forma inmediata las formas de dosificación, mientras que los 25 sistemas SEDDS semisólidos liberan de forma sostenida las formas de dosificación.
Ejemplo 4
[0095] Los sistemas SEDDS Tipo I, Tipo II y Tipo III preferidos son de naturaleza isotrópica con un comportamiento
30 de fase uniforme antes de la dilución en medio acuoso. Las fórmulas de SEDDS separadas en fases, que no son de naturaleza isotrópica, muestran agrietamiento o mala uniformidad de matriz en el caso de semisólidos. La Tabla 4 a continuación muestra los resultados de los exámenes de comportamiento de fase para seleccionar SEDDS, formulaciones de placebo que utilizan combinaciones de un medio portador oleoso con Labrasol. Los exámenes fueron macroscópicos (es decir, visuales), así como microscópicos (Olympus® Stereomicroscope).
35 TABLA 4
Ingrediente
(e) mg (%) (f) mg (%) (g) mg (%)
ESTADO FÍSICO
Líquido Semisólido fluido Semisólido
Agente activo
0 (3,85) 0 (3,85) 0 (3,85)
Componente de Aceite/ Portador de Ácido Graso (por ejemplo Ácido Oleico)
121,75 (46,8) 158,0 (60,8) 112,5 (43,1)
Componente de Tensioactivo (por ejemplo, Labrasol)
121,75 (46,8) 79,0 (30,4) 112,5 (43,1)
Palmitato de ascorbilo
6,5 (2,5) 13,0 (5,0) 26,0 (10,0)
13
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Claims (1)

  1. imagen1
    imagen2
ES06827524.7T 2005-11-07 2006-11-03 Administración mejorada de tetahidrocannabinol Active ES2581212T3 (es)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US73416005P 2005-11-07 2005-11-07
US734160P 2005-11-07
PCT/US2006/043126 WO2007056242A1 (en) 2005-11-07 2006-11-03 Improved delivery of tetrahydrocannabinol

Publications (1)

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ES2581212T3 true ES2581212T3 (es) 2016-09-02

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US (1) US20070104741A1 (es)
EP (1) EP1903866B1 (es)
JP (1) JP2009514890A (es)
AU (1) AU2006311818B9 (es)
CA (1) CA2618705C (es)
DK (1) DK1903866T3 (es)
ES (1) ES2581212T3 (es)
PT (1) PT1903866E (es)
WO (1) WO2007056242A1 (es)

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