Clinical data | |
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AHFS/Drugs.com | Monograph |
MedlinePlus | a607048 |
Routes of administration | Oral form (PO)- capsule |
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Pharmacokinetic data | |
Bioavailability | 20% after first-pass by the liver |
Protein binding | similar to THC (+/-97%) |
Elimination half-life | 2 hours, with metabolites around 35 hours. |
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KEGG | |
ChEMBL | |
ECHA InfoCard | 100.164.824 |
Chemical and physical data | |
Formula | C24H36O3 |
Molar mass | 372.541 g/mol g·mol−1 |
3D model (JSmol) | |
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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 (CINV) 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. In Austria Nabilone is marketed as Canemes and got its approval for CINV in 2013.[2]
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[3] and multiple sclerosis.[4]
Nabilone is a racemic mixture consisting of the (S,S) and the (R,R) isomers ("trans").
Nabilone has shown modest effectiveness in relieving fibromyalgia.[3] A 2011 systematic review of cannabinoids for chronic pain determined there was evidence of safety and modest efficacy for some conditions.[5]
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.[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. These patients made up only a small fraction of the study's population, and the study was not designed to identify subgroups.[8] Nabilone was tested as a adjunct for diabetic neuropathic pain and considered well tolerated.[9]
A clinical trial performed in Canada reviewed the use of nabilone to treat nightmares in individuals suffering from post-traumatic stress syndrome.[10] 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.[10] This study is limited to by lack of placebo control, but warrants future investigation into the use of cannabinoids for 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.
A subsequent double-blind study found that nabilone was effective for PTSD nightmares.[11]
Nabilone can increase, rather than decrease, post-operative pain; in the treatment of fibromyalgia, adverse effects limits the useful dose.[3] 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.[12]