Nabilone

Nabilone
	Top: (R,R)-(−)-nabilone,; Center: (S,S)-(+)-nabilone,; Bottom: Space-filling model of (R,R)-(−)-nabilone
Clinical data
Trade names	Cesamet, others
AHFS/Drugs.com	Monograph
MedlinePlus	a607048
Routes of; administration	By mouth
Drug class	Cannabinoid
ATC code	A04AD11 (WHO) ;
Legal status
Legal status	AU: S8 (Controlled drug); CA: Schedule II; DE: Anlage III (Special prescription form required); 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%)
Elimination half-life	2 hours, with metabolites around 35 hours
Identifiers
	IUPAC name rel-(6aR,10aR)-1-Hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-6,6a,7,8,10,10a-hexahydro-9H-benzo[c]chromen-9-one;
CAS Number	51022-71-0 ;
PubChem CID	5284592;
DrugBank	DB00486 ;
ChemSpider	4447641 ;
UNII	2N4O9L084N;
KEGG	D05099 ;
ChEMBL	ChEMBL947 ;
ECHA InfoCard	100.164.824
Chemical and physical data
Formula	C24H36O3
Molar mass	372.549 g·mol−1
3D model (JSmol)	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 ; Key:GECBBEABIDMGGL-RTBURBONSA-N ;
	(verify)

Nabilone, sold under the brand name Cesamet among others, is a synthetic cannabinoid with therapeutic use as an antiemetic and as an adjunct analgesic for neuropathic pain.^[1]^[2] It mimics tetrahydrocannabinol (THC), the primary psychoactive compound found naturally occurring in Cannabis.^[3]

The Food and Drug Administration (FDA) in the United States 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^[4] and multiple sclerosis.^[5]^[6]

^ "Nabilone - AdisInsight".
^ "Nabilone Advanced Patient Information".
^ "Nabilone label" (PDF). FDA. May 2006.
^ Cite error: The named reference pain was invoked but never defined (see the help page).
^ Wissel J, Haydn T, Müller J, Brenneis C, Berger T, Poewe W, Schelosky LD (October 2006). "Low dose treatment with the synthetic cannabinoid Nabilone significantly reduces spasticity-related pain : a double-blind placebo-controlled cross-over trial". Journal of Neurology (Research article). 253 (10): 1337–41. doi:10.1007/s00415-006-0218-8. PMID 16988792. S2CID 24206300.
^ Nielsen S, Germanos R, Weier M, Pollard J, Degenhardt L, Hall W, Buckley N, Farrell M (February 2018). "The Use of Cannabis and Cannabinoids in Treating Symptoms of Multiple Sclerosis: a Systematic Review of Reviews". Current Neurology and Neuroscience Reports. 18 (2): 8. doi:10.1007/s11910-018-0814-x. hdl:2123/18910. PMID 29442178. S2CID 3375801.

[AdisInsight-1] "Nabilone - AdisInsight".

[Drugs.com-2] "Nabilone Advanced Patient Information".

[USlabel2006-3] "Nabilone label" (PDF). FDA. May 2006.

[pain-4] Cite error: The named reference pain was invoked but never defined (see the help page).

[5] Wissel J, Haydn T, Müller J, Brenneis C, Berger T, Poewe W, Schelosky LD (October 2006). "Low dose treatment with the synthetic cannabinoid Nabilone significantly reduces spasticity-related pain : a double-blind placebo-controlled cross-over trial". Journal of Neurology (Research article). 253 (10): 1337–41. doi:10.1007/s00415-006-0218-8. PMID 16988792. S2CID 24206300.

[6] Nielsen S, Germanos R, Weier M, Pollard J, Degenhardt L, Hall W, Buckley N, Farrell M (February 2018). "The Use of Cannabis and Cannabinoids in Treating Symptoms of Multiple Sclerosis: a Systematic Review of Reviews". Current Neurology and Neuroscience Reports. 18 (2): 8. doi:10.1007/s11910-018-0814-x. hdl:2123/18910. PMID 29442178. S2CID 3375801.

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