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Nabilone

产品号 DB00486 公司名称 DrugBank
CAS号 51022-71-0 公司网站 http://www.ualberta.ca/
分子式 C24H36O3 电 话 (780) 492-3111
分子量 372.54084 传 真
纯 度 电子邮件 david.wishart@ualberta.ca
保 存 Chembase数据库ID: 369

产品价格信息

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产品别名

标题
Nabilone
IUPAC标准名
(6aR,10aR)-1-hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-6H,6aH,7H,8H,9H,10H,10aH-benzo[c]isochromen-9-one
IUPAC传统名
nabilone
商标名
Cesamet
别名
nabilone

产品登记号

PubChem SID 46505171
PubChem CID 5284592
CAS号 51022-71-0

产品性质

疏水性(logP) 6.8

产品详细信息

详细说明 (English)
Item Information
Drug Groups approved; investigational
Description 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").
Indication 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.
Pharmacology 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.
Toxicity 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.
Affected Organisms
Humans and other mammals
Biotransformation 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.
Absorption Rapidly absorbed from the gastrointestinal tract following oral administration.
Half Life 2 hours, with metabolites around 35 hours.
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.
Distribution * 12.5 L/kg
References
Cunningham D, Bradley CJ, Forrest GJ, Hutcheon AW, Adams L, Sneddon M, Harding M, Kerr DJ, Soukop M, Kaye SB: A randomized trial of oral nabilone and prochlorperazine compared to intravenous metoclopramide and dexamethasone in the treatment of nausea and vomiting induced by chemotherapy regimens containing cisplatin or cisplatin analogues. Eur J Cancer Clin Oncol. 1988 Apr;24(4):685-9. [Pubmed]
Niiranen A, Mattson K: Antiemetic efficacy of nabilone and dexamethasone: a randomized study of patients with lung cancer receiving chemotherapy. Am J Clin Oncol. 1987 Aug;10(4):325-9. [Pubmed]
Herman TS, Einhorn LH, Jones SE, Nagy C, Chester AB, Dean JC, Furnas B, Williams SD, Leigh SA, Dorr RT, Moon TE: Superiority of nabilone over prochlorperazine as an antiemetic in patients receiving cancer chemotherapy. N Engl J Med. 1979 Jun 7;300(23):1295-7. [Pubmed]
Einhorn LH, Nagy C, Furnas B, Williams SD: Nabilone: an effective antiemetic in patients receiving cancer chemotherapy. J Clin Pharmacol. 1981 Aug-Sep;21(8-9 Suppl):64S-69S. [Pubmed]
External Links
Wikipedia
Drugs.com

参考文献

  • Cunningham D, Bradley CJ, Forrest GJ, Hutcheon AW, Adams L, Sneddon M, Harding M, Kerr DJ, Soukop M, Kaye SB: A randomized trial of oral nabilone and prochlorperazine compared to intravenous metoclopramide and dexamethasone in the treatment of nausea and vomiting induced by chemotherapy regimens containing cisplatin or cisplatin analogues. Eur J Cancer Clin Oncol. 1988 Apr;24(4):685-9. Pubmed
  • Niiranen A, Mattson K: Antiemetic efficacy of nabilone and dexamethasone: a randomized study of patients with lung cancer receiving chemotherapy. Am J Clin Oncol. 1987 Aug;10(4):325-9. Pubmed
  • Herman TS, Einhorn LH, Jones SE, Nagy C, Chester AB, Dean JC, Furnas B, Williams SD, Leigh SA, Dorr RT, Moon TE: Superiority of nabilone over prochlorperazine as an antiemetic in patients receiving cancer chemotherapy. N Engl J Med. 1979 Jun 7;300(23):1295-7. Pubmed
  • Einhorn LH, Nagy C, Furnas B, Williams SD: Nabilone: an effective antiemetic in patients receiving cancer chemotherapy. J Clin Pharmacol. 1981 Aug-Sep;21(8-9 Suppl):64S-69S. Pubmed