Nabilone

Nabilone

File:Nabilone.png
Clinical data
Pregnancy category	NA
Routes of administration	Oral form (PO)- capsule
ATC code	A04AD11 (WHO)
Legal status
Legal status	US: Schedule II
Pharmacokinetic data
Bioavailability	20% after first-pass by the liver
Protein binding	similar to THC (+/-97%)
Elimination half-life	2 hours, with metabolites around 35 hours.
Identifiers
IUPAC name (6aR,10aR)-1-hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)- -7,8,10,10a-tetrahydro-6H-benzo[c]chromen-9(6aH)-one
CAS Number	51022-71-0
PubChem CID	5284592
DrugBank	APRD01127
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C24H36O3
Molar mass	372.541 g/mol

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 demonstrated various benefits for condition such as fibromyalgia and multiple sclerosis .

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

Clinical trials

The main settings that have seen published clinical trials of nabilone include movement disorders such as Parkinson's syndrome, chronic pain, dystonia and spasticity neurological disorders, fibromyalgia, multiple sclerosis, and the nausea of cancer chemotherapy.

A study comparing nabilone with metoclopramide, conducted before the development of modern 5-HT3 inhibitor anti-emetics such as ondansetron, revealed that patients taking cisplatin chemotherapy preferred metoclopramide, while patients taking carboplatin chemotherapy preferred nabilone to control nausea and vomiting. Another study compared nabilone alone to nabilone with dexamethasone. The study found that the combination worked better than the single medication. 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. A follow-up to this study revealed similar findings.