Nabilone
1672028
223705204
2008-07-05T10:36:34Z
DOI bot
6652755
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{{drugbox
| IUPAC_name = (6a''R'',10a''R'')-1-hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-
-7,8,10,10a-tetrahydro-6H-benzo[c]chromen-9(6aH)-one
| image = Nabilone.png
| width = 180
| CAS_number = 51022-71-0
| ATC_prefix = A04
| ATC_suffix = AD11
| ATC_supplemental =
| PubChem = 5284592
| DrugBank = APRD01127
| C=24 | H=36 | O=3
| molecular_weight = 372.541 g/mol
| bioavailability = 20% after first-pass by the liver
| protein_bound = similar to THC (+/-97%)
| T-max = 2 hours
| duration of action = 8-12 hours
| onset of action = 60-90 minutes
| THC equivalence = 1mg = 10mg THC
| metabolism =
| Number of metabolite = 2 actives metabolites
| Excretion = Feces(65%)and urine(20%)
| elimination_half-life = 2 hours, with metabolites around 35 hours.
| Marijuana Drug test (EMIT) = negative
| pregnancy_category = NA
| legal_US = Schedule II
| routes_of_administration = Oral form (PO)- capsule
| Availability = 0.5 mg and 1 mg 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 [[cannabis (drug)|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]] <ref>{{cite journal |author= Skrabek RQ, Galimova L, Ethans K, Perry D|title=Nabilone for the treatment of pain in fibromyalgia |journal= J Pain|volume=9 |issue=2 |pages=164–73 |year=2008 |pmid=17974490|doi=10.1016/j.jpain.2007.09.002}}</ref> and [[multiple sclerosis]]. <ref>{{cite journal |author= Wissel J, Haydn T, Müller J, Brenneis C, Berger T, Poewe W, Schelosky LD.|title=Low dose treatment with the synthetic cannabinoid Nabilone significantly reduces spasticity-related pain : a double-blind placebo-controlled cross-over trial |journal= J Neurol. |volume=253 |issue=10 |pages=1337–41 |year=2006 |pmid=16988792|doi=10.1007/s00415-006-0218-8}}</ref>
Nabilone is a [[racemic mixture]] consisting of the ''(S,S)'' and the ''(R,R)'' [[isomer]]s (''"[[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.
<ref>{{cite journal |author=Cunningham D, Bradley C, Forrest G, Hutcheon A, Adams L, Sneddon M, Harding M, Kerr D, Soukop M, Kaye S |title=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 |journal=Eur J Cancer Clin Oncol |volume=24 |issue=4 |pages=685–9 |year=1988 |pmid=2838294 |doi=10.1016/0277-5379(88)90300-8}}</ref>
Another study compared nabilone alone to nabilone with [[dexamethasone]]. The study found that the combination worked better than the single medication.
<ref>{{cite journal |author=Niiranen A, Mattson K |title=Antiemetic efficacy of nabilone and dexamethasone: a randomized study of patients with lung cancer receiving chemotherapy |journal=Am J Clin Oncol |volume=10 |issue=4 |pages=325–9 |year=1987 |pmid=3039831}}</ref>
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.
<ref>{{cite journal |author=Herman T, Einhorn L, Jones S, Nagy C, Chester A, Dean J, Furnas B, Williams S, Leigh S, Dorr R, Moon T |title=Superiority of nabilone over prochlorperazine as an antiemetic in patients receiving cancer chemotherapy |journal=N Engl J Med |volume=300 |issue=23 |pages=1295–7 |year=1979 |pmid=375088}}</ref>
A follow-up to this study revealed similar findings.
<ref>{{cite journal |author=Einhorn L, Nagy C, Furnas B, Williams S |title=Nabilone: an effective antiemetic in patients receiving cancer chemotherapy |journal=J Clin Pharmacol |volume=21 |issue=8-9 Suppl |pages=64S–69S |year= |pmid=6271844}}</ref>
One study compared the efficacy and tolerability of nabilone with that of [[dihydrocodeine]] in the treatment of [[neuropathy|neuropathic pain]].<ref>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}}</ref> The authors found that nabilone was not as effective as dihydrocodeine in controlling pain, and caused a higher incidence of minor [[adverse drug reaction]]s 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.<ref>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}}</ref>
==References==
{{Reflist|2}}
{{Antiemetics and antinauseants}}
{{Cannabinoids}}
[[Category:Cannabinoids]]
{{Hallucinogen-stub}}
{{Pharma-stub}}
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