User:Mr. Ibrahem/Nabilone

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Mr. Ibrahem/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 classSynthetic cannabinoid[1]
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
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 medication used for chemotherapy-induced nausea and vomiting.[1] Some evidence supports modest effectiveness for fibromyalgia and multiple sclerosis.[3][4] It is taken by mouth.[2]

Common side effects include sleepiness, dry mouth, dizziness, feeling high, poor coordination, and headache.[1] Other side effects may include fast heart rate, abuse, and psychosis.[1] Safety in pregnancy is unclear.[1] It is a synthetic cannabinoid which effects similar to tetrahydrocannabinol (THC), the primary psychoactive compound found in Cannabis.[1][5]

Nabilone was approved for medical use in the United States in 1985.[1] In the United Kingdom 20 pills of 1 mg costs the NHS about £200 as of 2021.[2] This amount in the United States costs about 820 USD.[6] In the United States it is a schedule II controlled substance.[1]

References[edit]

  1. ^ a b c d e f g h i j "Nabilone Monograph for Professionals". Drugs.com. Archived from the original on 19 October 2020. Retrieved 11 November 2021.
  2. ^ a b c BNF 81: March-September 2021. BMJ Group and the Pharmaceutical Press. 2021. p. 451. ISBN 978-0857114105.
  3. ^ Fine PG, Rosenfeld MJ (2013). "The endocannabinoid system, cannabinoids, and pain". Rambam Maimonides Medical Journal (Review). 4 (4): e0022. doi:10.5041/RMMJ.10129. PMC 3820295. PMID 24228165.
  4. ^ 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.
  5. ^ "DailyMed - CESAMET- nabilone capsule". dailymed.nlm.nih.gov. Archived from the original on 25 March 2021. Retrieved 11 November 2021.
  6. ^ "Cesamet Prices, Coupons & Patient Assistance Programs". Drugs.com. Archived from the original on 9 April 2021. Retrieved 11 November 2021.
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