Nabilone

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Nabilone
Systematic (IUPAC) name
?
Identifiers
CAS number	51022-71-0
ATC code	A04AD11
PubChem	5284592
DrugBank	APRD01127
Chemical data
Formula	C24H36O3
Mol. mass	372.541 g/mol
Pharmacokinetic data
Bioavailability	20% after first-pass by the liver
Metabolism	?
Half life	2 hours, with metabolites around 35 hours.
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status	Schedule II (USA)
Routes	?

Nabilone is a synthetic cannabinoid with therapeutic use as an antiemetic. It is an analog of dronabinol (also known as tetrahydrocannabinol or THC), the psychoactive ingredient in cannabis[1]. Nabilone is not derived from the marijuana plant as is dronabinol.

In Canada, the United States, and the United Kingdom, 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.

Nabilone is a racemate consisting of the (S,S) and the (R,R) isomers ("trans").

[edit] Clinical trials

The main settings that have seen published clinical trials of nabilone include movement disorders such as Parkinson's syndrome, dystonia and spasticity neurological disorders, and the nausea of cancer chemotherapy. A study comparing nabilone with metoclopramide, conducted before the modern era of 5-HT3 inhibitor anti-emetic therapy, revealed that patients taking cisplatin chemotherapy preferred metoclopramide, while patients taking carboplatin chemotherapy preferred nabilone to control nausea and vomiting. ^[1] Another study compared nabilone alone to nabilone with dexamethasone. The study found that the combination worked better than the single medication. ^[2] An older study revealed that nabilone was more effective than prochlorperazine in controlling nausea, though in this study, only 9% of nabilone patients had complete resolution of symptoms. ^[3] A follow-up to this study revealed similar findings. ^[4]

The nabilone package insert cites the existence of placebo-controlled clinical trials demonstrating superior efficacy of nabilone. These placebo-controlled trials are not available in the published literature, though they are referenced by corporate news press releases by the manufacturer, Valeant.

[edit] References

1. ^ Cunningham D, Bradley C, Forrest G, Hutcheon A, Adams L, Sneddon M, Harding M, Kerr D, Soukop M, Kaye S (1988). "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 24 (4): 685-9. PMID 2838294. 
2. ^ Niiranen A, Mattson K (1987). "Antiemetic efficacy of nabilone and dexamethasone: a randomized study of patients with lung cancer receiving chemotherapy". Am J Clin Oncol 10 (4): 325-9. PMID 3039831. 
3. ^ Herman T, Einhorn L, Jones S, Nagy C, Chester A, Dean J, Furnas B, Williams S, Leigh S, Dorr R, Moon T (1979). "Superiority of nabilone over prochlorperazine as an antiemetic in patients receiving cancer chemotherapy". N Engl J Med 300 (23): 1295-7. PMID 375088. 
4. ^ Einhorn L, Nagy C, Furnas B, Williams S. "Nabilone: an effective antiemetic in patients receiving cancer chemotherapy". J Clin Pharmacol 21 (8-9 Suppl): 64S-69S. PMID 6271844. 

• Compounds That Bind to Cannabinoid Receptors, Table 2.2, Marijuana and Medicine: Assessing the Science Base, Institute of Medicine.