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07-SEPTEMBER-2008 03:17:44 - Nabilone Nabilone Systematic IUPAC name 6aR,10aR-1-hydroxy-6,6-dimethyl-3-2-methyloctan-2-yl- -7,8,10,10a-tetrahydro-6H-benzocchromen-96aH-one Identifiers CAS number 51022-71-0 ATC code A04AD11 PubChem 5284592 DrugBank APRD01127 Chemical data Formula C24H36O3 Mol. mass 372.541 g/mol Pharmacokinetic data Bioavailability 20% after first-pass by the liver Protein binding similar to THC +/-97% Metabolism ? Half life 2 hours, with metabolites around 35 hours. Excretion ? Therapeutic considerations Pregnancy cat. NA Legal status Schedule IIUS Routes Oral form PO- capsule 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. 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 1 and multiple sclerosis. 2 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. 3 Another study compared nabilone alone to nabilone with dexamethasone. The study found that the combination worked better than the single medication. 4 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. 5 A follow-up to this study revealed similar findings. 6 One study compared the efficacy and tolerability of nabilone with that of dihydrocodeine in the treatment of neuropathic pain.7 The authors found that nabilone was not as effective as dihydrocodeine in controlling pain, and caused a higher incidence of minor adverse drug reactions than did dihydrocodeine. One critic of the study has suggested that nabilone might be best suited for the treatment of patients suffering from central and spasticity-related pain, for which there is stronger evidence for the benefits of cannabinoid therapy; however, these patients made up only a small fraction of the study's population, and the study was not designed to identify subgroups which might have responded more favorably to treatment than others.8 References ^ Skrabek RQ, Galimova L, Ethans K, Perry D 2008. Nabilone for the treatment of pain in fibromyalgia. J Pain 9 2: 164-73. doi:10.1016/j.jpain.2007.09.002. PMID 17974490. ^ Wissel J, Haydn T, Müller J, Brenneis C, Berger T, Poewe W, Schelosky LD. 2006. Low dose treatment with the synthetic cannabinoid Nabilone significantly reduces spasticity-related pain : a double-blind placebo-controlled cross-over trial. J Neurol. 253 10: 1337-41. doi:10.1007/s00415-006-0218-8. PMID 16988792. ^ Cunningham D, Bradley C, Forrest G, Hutcheon A, Adams L, Sneddon M, Harding M, Kerr D, Soukop M, Kaye S 1988. A randomized trial of oral nabilone and prochlorperazine compared to intravenous metoclopramide and dexamethasone in the treatment of nausea and vomiting induced by chemotherapy regimens containing cisplatin or cisplatin analogues. Eur J Cancer Clin Oncol 24 4: 685-9. doi:10.1016/0277-53798890300-8. PMID 2838294. ^ Niiranen A, Mattson K 1987. Antiemetic efficacy of nabilone and dexamethasone: a randomized study of patients with lung cancer receiving chemotherapy. Am J Clin Oncol 10 4: 325-9. PMID 3039831. ^ Herman T, Einhorn L, Jones S, Nagy C, Chester A, Dean J, Furnas B, Williams S, Leigh S, Dorr R, Moon T 1979. Superiority of nabilone over prochlorperazine as an antiemetic in patients receiving cancer chemotherapy. N Engl J Med 300 23: 1295-7. PMID 375088. ^ Einhorn L, Nagy C, Furnas B, Williams S. Nabilone: an effective antiemetic in patients receiving cancer chemotherapy. J Clin Pharmacol 21 8-9 Suppl: 64S-69S. PMID 6271844. ^ Frank B, Serpell MG, Hughes J, Matthews JN, Kapur D. Comparison of analgesic effects and patient tolerability of nabilone and dihydrocodeine for chronic neuropathic pain: randomised, crossover, double blind study. British Medical Journal. 2008 Jan 8. Epub ahead of print. PMID 18182416. doi:10.1136/bmj.39429.619653.80 ^ Cohen SP. Cannabinoids for chronic pain. British Medical Journal. 2008 Jan 8. Epub ahead of print. PMID 18182415. doi:10.1136/bmj.39434.444583.80 v d e Antiemetics and antinauseants A04 Serotonin 5-HT3 antagonists Azasetron Dolasetron Ondansetron Granisetron Palonosetron Ramosetron Tropisetron Dopamine antagonists Alizapride Domperidone Metoclopramide Metopimazine Prochlorperazine Antihistamines Cyclizine Meclizine Promethazine NK1 receptor antagonists Aprepitant Casopitant Fosaprepitant Cannabinoids Dronabinol Nabilone Benzodiazepines Lorazepam Midazolam Anticholinergics Scopolamine Corticosteroids Dexamethasone Other Cerium oxalate Chlorobutanol Propofol Trimethobenzamide v d e Cannabinoids Plant cannabinoids CBD CBDV CBN CBG CBV CBL THC THC-C4 THCV Cannabinoid metabolites 11-Hydroxy-THC 11-nor-9-Carboxy-THC Endogenous cannabinoids Arachidonoyl ethanolamide Anandamide or AEA 2-Arachidonoylglycerol 2-AG 2-Arachidonyl glyceryl ether noladin ether Virodhamine N-arachidonoyl-dopamine NADA; Oleamide Synthetic cannabinoid agonists Classical cannabinoids Dibenzopyrans A-41988 Ajulemic acid AM-087 AM-411 AM-855 AM-905 AM-906 AM-919 AM-938 AM-4030 AMG-1 AMG-3 AMG-36 AMG-41 Dexanabinol HU-211 DMHP Dronabinol HU-210 JWH-051 JWH-133 JWH-139 L-759,633 L-759,656 Levonantradol Nabilone Nabitan O-806 O-823 O-1057 O-1125 O-1238 O-2545 O-2694 Parahexyl THC-O-acetate THC-O-phosphate Nonclassical cannabinoids CP 47,497 CP 55,244 CP 55,940 HU-308 2-Isopropyl-5-methyl-1-2,6-dihydroxy-4-nonylphenylcyclohex-1-ene Aminoalkylindoles AM-630 AM-1241 JWH-015 JWH-018 JWH-073 JWH-081 JWH-200 L-768,242 Pravadoline WIN 55,212-2 Aminoalkylpyrroles JWH-030 JWH-147 JWH-307 Eicosanoids AM-883 Arachidonyl-2'-chloroethylamide Arachidonylcyclopropylamide Methanandamide O-585 O-689 O-1812 O-1860 O-1861 Others BAY 38-7271 BAY 59-3074 GW 842,166X JWH-171 O-2220 Endocannabinoid activity enhancers AM-404 CAY-10401 CAY-10402 N-arachidonoyl-serotonin O-1624 PF-622 PF-750 URB-597 URB-602 URB-754 Cannabinoid antagonists and inverse agonists AM-251 AM-281 AM-630 AVE-1625 BML-190 CAY-10508 CB-25 CB-52 JTE-907 LY-320,135 MK-9470 NESS-0327 O-1184 O-2050 O-2654 Rimonabant SLV-319 SR-144,528 Surinabant Taranabant VCHSR This article related to psychedelics, dissociatives and deliriants is a stub. Tablets This pharmacology-related article is a stub. Retrieved from http://en..org/wiki/Nabilone Categories: Cannabinoids | Hallucinogen stubs | Pharmacology stubs Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Deutsch Français Italiano Polski Svenska This page was last modified on 5 July 2008, at 10:3
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