Nabilone

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Nabilone
Nabilone2D.svg
Nabilone3Dan2.gif
Systematic (IUPAC) name
(6aR,10aR)-rel-1-hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-
Clinical data
AHFS/Drugs.com monograph
MedlinePlus a607048
Pregnancy cat. C (US)
Legal status Controlled (S8) (AU) POM (UK) Schedule II (US)
Routes Oral form (PO)- capsule
Pharmacokinetic data
Bioavailability 20% after first-pass by the liver
Protein binding similar to THC (+/-97%)
Half-life 2 hours, with metabolites around 35 hours.
Identifiers
CAS number 51022-71-0 YesY
ATC code A04AD11
PubChem CID 5284592
DrugBank DB00486
ChemSpider 4447641 YesY
UNII 2N4O9L084N YesY
KEGG D05099 YesY
ChEMBL CHEMBL947 YesY
Chemical data
Formula C24H36O3 
Mol. mass 372.541 g/mol
 YesY (what is this?)  (verify)

Nabilone is a synthetic cannabinoid with therapeutic use as an antiemetic and as an adjunct analgesic for neuropathic pain. It mimics the main chemical compound of cannabis (THC), the active ingredient found in naturally occurring Cannabis sativa L.[1]

In Canada, the United States, the United Kingdom and Mexico, nabilone is marketed as Cesamet. It was approved in 1985 by the U.S. Food and Drug Administration (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.[citation needed]

Although it doesn't have any indication officially (except in Mexico), nabilone is widely used as an adjunct therapy for chronic pain management. Numerous trials and case studies have demonstrated modest effectiveness for relieving fibromyalgia[2] and multiple sclerosis.[3]

Nabilone is a racemic mixture consisting of the (S,S) and the (R,R) isomers ("trans").

Medical uses[edit]

Nabilone has shown modest effectiveness in relieving fibromyalgia.[2]

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, multiple sclerosis, and the nausea of cancer chemotherapy. Nabilone is also effective in the treatment of inflammatory bowel disease, especially ulcerative colitis. Medical marijuana patients report that nabilone is more similar in effect to CBD than THC, indicating that it has more of a therapeutic effect on the body than a "high" effect on the mind.[citation needed]

A study comparing nabilone with metoclopramide, conducted before the development of modern 5-HT3 antagonist 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.[4]

One study compared the efficacy and tolerability of nabilone with that of dihydrocodeine in the treatment of neuropathic pain.[5] 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.[6]

A clinical trial performed in Canada reviewed the use of nabilone to treat nightmares in individuals suffering from post-traumatic stress syndrome.[7] The study found that nighttime administration of nabilone reduced the frequency and/or intensity of nightmares in 34 out of 47 (72%) of patients, with 28 reporting complete cessation of nightmares.[7] This study is limited to the extent that there was no placebo control, but warrants future investigation into the use of cannabinoid therapy in the treatment of post-traumatic stress syndrome and other disorders involving recurrent nightmares. As endocannabinoids play a significant role in regulating long-term depression, perhaps downregulating the CB1 system can help remove the highly potentiated, hippocampal/amydygalia memories of the fear. At the very least, CB1 agonists make one less likely to remember a dream, or even make REM sleep happen without significant involvement of the limbic system.

Adverse effects[edit]

Nabilone can increase, rather than decrease, post-operative pain; in the treatment of fibromyalgia, adverse effects limits the useful dose.[2] Adverse effects of nabilone include, but are not limited to dizziness/vertigo, euphoria, drowsiness, dry mouth, ataxia, sleep disturbance, dysphoria, headache, nausea, disorientation, depersonalization, asthenia and increased appetite.[8]

See also[edit]

References[edit]

  1. ^ "How to use Cesamet". Artek LLC. 2008. 
  2. ^ a b c Fine PG, Rosenfeld MJ (2013). "The endocannabinoid system, cannabinoids, and pain". Rambam Maimonides Med J (Review) 4 (4): e0022. doi:10.5041/RMMJ.10129. PMC 3820295. PMID 24228165. 
  3. ^ [non-primary source needed]Wissel J, et al. (2006). "Low dose treatment with the synthetic cannabinoid Nabilone significantly reduces spasticity-related pain : a double-blind placebo-controlled cross-over trial". J Neurol. (Research article) 253 (10): 1337–41. doi:10.1007/s00415-006-0218-8. PMID 16988792. 
  4. ^ [non-primary source needed]Cunningham D, et al. (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 (Randomized controlled trial) 24 (4): 685–9. doi:10.1016/0277-5379(88)90300-8. PMID 2838294. 
  5. ^ [non-primary source needed]Frank B, Serpell MG, Hughes J, Matthews JN, Kapur D (January 2008). "Comparison of analgesic effects and patient tolerability of nabilone and dihydrocodeine for chronic neuropathic pain: randomised, crossover, double blind study". BMJ (Randomized controlled trial) 336 (7637): 199–201. doi:10.1136/bmj.39429.619653.80. PMC 2213874. PMID 18182416. 
  6. ^ [non-primary source needed]Cohen SP (January 2008). "Cannabinoids for chronic pain". BMJ (Research article) 336 (7637): 167–8. doi:10.1136/bmj.39434.444583.80. PMC 2213791. PMID 18182415. 
  7. ^ a b [non-primary source needed]Fraser, GA (2009). "The Use of a Synthetic Cannabinoid in the Management of Treatment-Resistant Nightmares in Posttraumatic Stress Disorder (PTSD)". CNS Neurosci Ther (Trial report) 15 (1): 84–88. doi:10.1111/j.1755-5949.2008.00071.x. PMID 19228182. 
  8. ^ "Cesamet (nabilone) Prescribing Information". http://www.cesamet.com/pdf/Cesamet_PI_50_count.pdf. Meda Pharmaceuticals Inc. Retrieved 16 July 2014.