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Nabilone

Nabilone
Skeletal formula of nabilone
Space-filling model of the nabilone molecule
Top: (R,R)-(−)-nabilone,
Center: (S,S)-(+)-nabilone,
Bottom: Space-filling model of (R,R)-(−)-nabilone
Clinical data
Trade namesCesamet, Canemes
AHFS/Drugs.comMonograph
MedlinePlusa607048
Routes of
administration		By mouth (capsules)
Drug classCannabinoid
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability20% after first-pass by the liver
Protein bindingsimilar to THC (±97%)
Elimination half-life2 hours, with metabolites around 35 hours
Identifiers
  • 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
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
ECHA InfoCard100.164.824 Edit this at Wikidata
Chemical and physical data
FormulaC24H36O3
Molar mass372.549 g·mol−1
3D model (JSmol)
  • O=C3CC[C@@H]1[C@H](c2c(OC1(C)C)cc(cc2O)C(C)(C)CCCCCC)C3
  • 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 checkY
  • Key:GECBBEABIDMGGL-RTBURBONSA-N checkY
  (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 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]

  1. ^ "Nabilone - AdisInsight".
  2. ^ "Nabilone Advanced Patient Information".
  3. ^ "Nabilone label" (PDF). FDA. May 2006.
  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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