Nabilone

Nabilone

Top: (R,R)-(−)-nabilone, Center: (S,S)-(+)-nabilone, Bottom: Space-filling model of (R,R)-(−)-nabilone
Clinical data
Trade names	Cesamet, Canemes
AHFS/Drugs.com	Monograph
MedlinePlus	a607048
Pregnancy category	US: C (Risk not ruled out)
Routes of administration	By mouth (capsules)
ATC code	A04AD11 (WHO)
Legal status
Legal status	AU: S8 (Controlled) CA: Schedule II DE: Anlage III (Prescription only) UK: POM (Prescription only) US: Schedule II In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	20% after first-pass by the liver
Protein binding	similar to THC (±97%)
Biological half-life	2 hours, with metabolites around 35 hours
Identifiers
IUPAC name (6aR,10aR)-rel-1-Hydroxy-6,6-dimethyl-3-(2-methyl-2-octanyl)-6,6a,7,8,10,10a-hexahydro-9H-benzo[c]chromen-9-one
CAS Number	51022-71-0 Y
PubChem CID	5284592
DrugBank	DB00486 Y
ChemSpider	4447641 Y
UNII	2N4O9L084N
KEGG	D05099 Y
ChEMBL	CHEMBL947 Y
ECHA InfoCard	100.164.824
Chemical and physical data
Formula	C24H36O3
Molar mass	372.541 g/mol
3D model (Jmol)	Interactive image
SMILES O=C3CC[C@@H]1[C@H](c2c(OC1(C)C)cc(cc2O)C(C)(C)CCCCCC)C3
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 Y Key:GECBBEABIDMGGL-RTBURBONSA-N Y

Nabilone is a synthetic cannabinoid with therapeutic use as an antiemetic and as an adjunct analgesic for neuropathic pain. It mimics tetrahydrocannabinol (THC), the primary psychoactive compound found naturally occurring in Cannabis.

The FDA in the USA has indicated nabilone for chemotherapy-induced nausea/vomiting. In other countries, such as Canada, it is widely used as an adjunct therapy for chronic pain management. Numerous trials and case studies have demonstrated modest effectiveness for relieving fibromyalgia and multiple sclerosis.

Nabilone is a racemic mixture consisting of (S,S)-(+)- and (R,R)-(−)-isomers (cis-trans isomerism).

Nabilone is used to treat nausea and vomiting in people under chemotherapy.

Nabilone has shown modest effectiveness in relieving fibromyalgia. A 2011 systematic review of cannabinoids for chronic pain determined there was evidence of safety and modest efficacy for some conditions.

The main settings that have seen published clinical trials of nabilone include movement disorders such as parkinsonism, chronic pain, dystonia and spasticity neurological disorders, multiple sclerosis, and the nausea of cancer chemotherapy. Nabilone is also effective in the treatment of inflammatory bowel disease, especially ulcerative colitis. Medical cannabis patients report that nabilone is more similar in effect to cannabidiol (CBD) than tetrahydrocannabinol (THC), indicating that it has more of a therapeutic effect on the body than a "high" effect on the mind.