Tìm theo
Nabilone
Các tên gọi khác (5 ) :
  • Cesamet
  • Nabilon
  • Nabilona
  • Nabilone
  • Nabilonum
Thuốc Gốc
Small Molecule
CAS: 51022-71-0
ATC: A04AD11
ĐG : Meda AB , http://www.meda.se
CTHH: C24H36O3
PTK: 372.5408
Nabilone is a synthetic cannabinoid with therapeutic use as an antiemetic and as an adjunct analgesic for neuropathic pain. It is a synthetic cannabinoid, which mimics the main ingredient of marijuana (THC) but it has more predictable side effects and causes no or minimal euphoria. Nabilone is not derived from the cannabis plant as is dronabinol. In Canada, the United States, the United Kingdom and Mexico, nabilone is marketed as Cesamet. It was approved in 1985 by the United States FDA for treatment of chemotherapy-induced nausea and vomiting that has not responded to conventional antiemetics. Though it was approved by the FDA in 1985, the drug only began marketing in the United States in 2006. It is also approved for use in treatment of anorexia and weight loss in patients with AIDS. Although it doesn't have the official indication (except in Mexico), nabilone is widely used as an adjunct therapy for chronic pain management. Numerous trials and case studies have demonstrate various benefits for condition such as fibromyalgia and multiple scerosis. Nabilone is a racemate consisting of the (S,S) and the (R,R) isomers ("trans").
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C24H36O3
Phân tử khối
372.5408
Monoisotopic mass
372.266445018
InChI
InChI=1S/C24H36O3/c1-6-7-8-9-12-23(2,3)16-13-20(26)22-18-15-17(25)10-11-19(18)24(4,5)27-21(22)14-16/h13-14,18-19,26H,6-12,15H2,1-5H3/t18-,19-/m1/s1
InChI Key
InChIKey=GECBBEABIDMGGL-RTBURBONSA-N
IUPAC Name
(6aR,10aR)-1-hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-6H,6aH,7H,8H,9H,10H,10aH-benzo[c]isochromen-9-one
Traditional IUPAC Name
nabilone
SMILES
[H][C@@]12CC(=O)CC[C@@]1([H])C(C)(C)OC1=CC(=CC(O)=C21)C(C)(C)CCCCCC
Độ hòa tan
4.93e-04 g/l
logP
6.8
logS
-5.9
pKa (strongest acidic)
9.33
pKa (Strongest Basic)
-4.9
PSA
46.53 Å2
Refractivity
110.2 m3·mol-1
Polarizability
44.91 Å3
Rotatable Bond Count
6
H Bond Acceptor Count
3
H Bond Donor Count
1
Physiological Charge
0
Number of Rings
3
Bioavailability
1
MDDR-Like Rule
true
Dược Lực Học : Nabilone is a cannabinoid with therapeutic uses. It is an analog of dronabinol (also known as tetrahydrocannabinol or THC), the psychoactive ingredient in cannabis. It is reserved for use in individuals who do not respond to the more commonly used anti-emetics. This is mainly because cannabinoids have potential adverse effects similar to that of cannabis and may cause changes in mood and behaviour.
Cơ Chế Tác Dụng : Nabilone is a synthetic cannabinoid with therapeutic use as an antiemetic and as an adjunct analgesic for neuropathic pain. It is a synthetic cannabinoid, which mimics the main ingredient of marijuana (THC) but it has more predictable side effects and causes no or minimal euphoria. Nabilone is not derived from the cannabis plant as is dronabinol. In Canada, the United States, the United Kingdom and Mexico, nabilone is marketed as Cesamet. It was approved in 1985 by the United States FDA for treatment of chemotherapy-induced nausea and vomiting that has not responded to conventional antiemetics. Though it was approved by the FDA in 1985, the drug only began marketing in the United States in 2006. It is also approved for use in treatment of anorexia and weight loss in patients with AIDS. Although it doesn't have the official indication (except in Mexico), nabilone is widely used as an adjunct therapy for chronic pain management. Numerous trials and case studies have demonstrate various benefits for condition such as fibromyalgia and multiple scerosis. Nabilone is a racemate consisting of the (S,S) and the (R,R) isomers ("trans"). The mode of action of nabilone has been studied in cats and dogs. Although its anti-emetic action is not yet fully understood, it is apparent that there are a number of points in the control systems of the body at which Nabilone could block the emetic mechanism. It is likely that nabilone exerts its actions via binding to the cannabinoid receptors.
Dược Động Học :
▧ Absorption :
Rapidly absorbed from the gastrointestinal tract following oral administration.
▧ Volume of Distribution :
* 12.5 L/kg
▧ Metabolism :
Hepatic. Two metabolic pathways have been suggested. The major pathway probably involves the direct oxidation of Nabilone to produce hydroxylic and carboxylic analogues. These compounds are thought to account for the remaining plasma radioactivity when carbinol metabolites have been extracted.
▧ Route of Elimination :
The route and rate of the elimination of nabilone and its metabolites are similar to those observed with other cannabinoids, including delta-9-THC (dronabinol). Therefore, it appears that the major excretory pathway is the biliary system.
▧ Half Life :
2 hours, with metabolites around 35 hours.
Độc Tính : Symptoms of overdose include difficulty in breathing, hallucinations, mental changes (severe), nervousness or anxiety (severe). Monkeys treated with Nabilone at doses as high as 2mg/kg/day for a year experienced no significant adverse events. This result contrasts with the finding in a planned 1-year dog study that was prematurely terminated because of deaths associated with convulsions in dogs receiving as little as 0.5mg/kg/day. The earliest deaths, however, occurred at 56 days in dogs receiving 2mg/kg/day. The unusual vulnerability of the dog is not understood; it is hypothesised, however, that the explanation lies in the fact that the dog differs markedly from other species (including humans) in its metabolism of Nabilone.
Chỉ Định : Used for the control of nausea and vomiting, caused by chemotherapeutic agents used in the treatment of cancer, in patients who have failed to respond adequately to conventional antiemetic treatments.
Tương Tác Thuốc :
  • Trimethobenzamide Anticholinergics, such as Trimethobenzamide, may increase the tachycardic effect of cannabinoids such as Nabilone. Close monitoring of cardiovascular effects is recommended.
  • Triprolidine The CNS depressants, Triprolidine and Nabilone, may increase adverse/toxic effects due to additivity. Monitor for increased CNS depressant effects during concomitant therapy.
  • Trospium Anticholinergics, such as Trospium, may increase the tachycardic effect of cannabinoids such as Nabilone. Close monitoring of cardiovascular effects is recommended.
Liều Lượng & Cách Dùng : Capsule - Oral
Dữ Kiện Thương Mại
Giá thị trường
  • Biệt dược thương mại : Cesamet 0.5 mg Capsule
    Giá bán buôn : USD >3.49
    Đơn vị tính : capsule
  • Biệt dược thương mại : Cesamet 1 mg capsule
    Giá bán buôn : USD >13.99
    Đơn vị tính : capsule
Nhà Sản Xuất
  • Công ty : Meda
    Sản phẩm biệt dược : Cesamet
  • Công ty : Meda
    Sản phẩm biệt dược : Nabilone
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00486
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=5284592
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46505171
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D05099
ChemSpider
http://www.chemspider.com/Chemical-Structure.4447641.html
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0187-1221-03
PharmGKB
http://www.pharmgkb.org/drug/PA164746998
Wikipedia
http://en.wikipedia.org/wiki/Nabilone
Drugs.com
http://www.drugs.com/cdi/nabilone.html
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