1. Cesamet
2. Lilly 109514
3. Ly 109514
4. Nabilone, (6ar-trans)-isomer
5. Nabilone, (6as-trans)-isomer
6. Nabilone, (cis-(+-))-isomer
7. Nabilone, (trans-(+-))-isomer
1. 51022-71-0
2. Cesamet
3. Chembl947
4. Lilly 109514
5. 2n4o9l084n
6. Cpd 109514
7. Cpd-109514
8. (6ar,10ar)-1-hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-7,8,10,10a-tetrahydro-6ah-benzo[c]chromen-9-one
9. Nabilona
10. Nabilonum
11. Nabilonum [latin]
12. Nabilona [spanish]
13. Nabilone [usan:inn:ban]
14. Unii-2n4o9l084n
15. 9h-dibenzo(b,d)pyran-9-one, 3-(1,1-dimethylheptyl)-6,6a,7,8,10,10a-hexahydro-1-hydroxy-6,6-dimethyl-, (6ar,10ar)-rel-
16. 9h-dibenzo[b,d]pyran-9-one, 3-(1,1-dimethylheptyl)-6,6a,7,8,10,10a-hexahydro-1-hydroxy-6,6-dimethyl-, (6ar,10ar)-rel-
17. Cesamet (tn)
18. (-)-nabilone
19. (?)-nabilone
20. Nabilone [usan]
21. Nabilone (usan/inn)
22. Nabilone [inn]
23. Nabilone [mi]
24. Nabilone [vandf]
25. Nabilone [mart.]
26. Nabilone [who-dd]
27. Schembl33339
28. Nabilone [orange Book]
29. Dea No. 7379
30. Dtxsid8023341
31. Dtxsid401015800
32. Zinc1542930
33. Bdbm50287941
34. Nabilone, Solid, >=98% (hplc)
35. Db00486
36. (+-)-3-(1,1-dimethylheptyl)-6,6abeta,7,8,10,10aalpha-hexahydro-1-hydroxy-6,6-dimethyl-9h-dibenzo(b,d)pyran-9-one
37. (+-)-trans-3-(1,1-dimethylheptyl)-6a,7,8,9,10,10a-hexahydro-1-hydroxy-6,6-dimethyl-6h-dibenzo(b,d)pyran-9-on
38. (+-)-trans-3-(1,1-dimethylheptyl-7,8,10,10a-tetrahydro-1-hydroxy-6,6-dimethyl-6h-dibenzo(b,d)pyran-9(6ah)-on
39. D05099
40. N-0100
41. 022n710
42. Q419079
43. (+-)-trans-3-(1,1-dimethylheptyl)-6,6a,7,8,10,10a-hexahydro-1-hydroxy-6,6-dimethyl-9h-dibenzo(b,d)pyran-9-one
44. (+/-)-3-(1,1-dimethylheptyl-6,6a.beta.,7,8,10,10a.alpha.-hexahydro-1-hydroxy-6,6-dimethyl-9h-dibenzo(b,d)pyran-9-one
45. (-)-trans-1-hydroxy-3-(1,1-dimethylheptyl)-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9h-dibenzo[b,d]-pyran-9-one
46. (-)-trans-1-hydroxy-3-(1,1-dimethylheptyl)-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9h-dibenzo[b,d]pyran-9-one
47. (-)-trans-3-(1,1-dimethylheptyl)-6,6a,7,8,10,10a-hexahydro-1-hydroxy-6,6-dimethyl-9h-dibenzo[b,d]pyran-9-one
48. (6ar,10ar)-1-hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-6h,6ah,7h,8h,9h,10h,10ah-benzo[c]isochromen-9-one
49. (6ar,10ar)-1-hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-7,8,10,10a-tetrahydro-6h-benzo[c]chromen-9(6ah)-one
50. (6ar,10ar)-3-(1,1-dimethyl-heptyl)-1-hydroxy-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-benzo[c]chromen-9-one
51. (6ar,10ar)-3-(1,1-dimethylheptyl)-1-hydroxy-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9h-benzo[c]chromen-9-one
52. 61617-09-2
53. 9h-dibenzo(b,d)pyran-9-one, 3-(1,1-dimethylheptyl)-6,6a,7,8,10,10a-hexahydro-1-hydroxy-6,6-dimethyl-, Trans-, (+-)-
54. 9h-dibenzo(b,d)pyran-9-one, 3-(1,1-dimethylheptyl)-6,6a,7,8,10,10a-hexahydro-1-hydroxy-6,6-dimethyl-, Trans-, (+/-)-
55. Trans-1-hydroxy-3-(1,1-dimethylheptyl)-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9h-dibenzo[b,d]-pyran-9-one
56. Trans-1-hydroxy-3-(1,1-dimethylheptyl)-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9h-dibenzo[b,d]pyran-9-one
57. Trans-3-(1',1'-dimethylheptyl)-6,6a,7,8,10,10a-hexahydro-1-hydroxy-6,6-dimethyl-9h-dibenzo[b,d]pyran-9-one
| Molecular Weight | 372.5 g/mol |
|---|---|
| Molecular Formula | C24H36O3 |
| XLogP3 | 6.4 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 6 |
| Exact Mass | 372.26644501 g/mol |
| Monoisotopic Mass | 372.26644501 g/mol |
| Topological Polar Surface Area | 46.5 Ų |
| Heavy Atom Count | 27 |
| Formal Charge | 0 |
| Complexity | 524 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 2 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently Bonded Unit Count | 1 |
| 1 of 2 | |
|---|---|
| Drug Name | Cesamet |
| PubMed Health | Nabilone (By mouth) |
| Drug Classes | Antiemetic |
| Drug Label | Cesamet (nabilone) is a synthetic cannabinoid for oral administration. Nabilone as a raw material occurs as a white to off-white polymorphic crystalline powder. In aqueous media, the solubility of nabilone is less than 0.5 mg/L, with pH values rang... |
| Active Ingredient | Nabilone |
| Dosage Form | Capsule |
| Route | Oral |
| Strength | 1mg |
| Market Status | Prescription |
| Company | Meda Pharms |
| 2 of 2 | |
|---|---|
| Drug Name | Cesamet |
| PubMed Health | Nabilone (By mouth) |
| Drug Classes | Antiemetic |
| Drug Label | Cesamet (nabilone) is a synthetic cannabinoid for oral administration. Nabilone as a raw material occurs as a white to off-white polymorphic crystalline powder. In aqueous media, the solubility of nabilone is less than 0.5 mg/L, with pH values rang... |
| Active Ingredient | Nabilone |
| Dosage Form | Capsule |
| Route | Oral |
| Strength | 1mg |
| Market Status | Prescription |
| Company | Meda Pharms |
Nabilone is indicated for the treatment of the nausea and vomiting associated with cancer chemotherapy in patients who have failed to respond adequately to conventional antiemetic treatments. This restriction is required because a substantial proportion of any group of patients treated with Nabilone can be expected to experience disturbing psychotomimetic reactions not observed with other antiemetic agents.
FDA Label
Nabilone is a cannabinoid with therapeutic uses. It is an analog of dronabinol (also known as tetrahydrocannabinol or THC), the psychoactive ingredient in cannabis. Although structurally distinct from THC, nabilone mimics THC's structure and pharmacological activity through weak partial agonist activity at Cannabinoid-1 (CB1R) and Cannabinoid-2 (CB2R) receptors, however it is considered to be twice as active as -THC.
Anti-Anxiety Agents
Agents that alleviate ANXIETY, tension, and ANXIETY DISORDERS, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions. ADRENERGIC BETA-ANTAGONISTS are commonly used in the symptomatic treatment of anxiety but are not included here. (See all compounds classified as Anti-Anxiety Agents.)
Antiemetics
Drugs used to prevent NAUSEA or VOMITING. (See all compounds classified as Antiemetics.)
A - Alimentary tract and metabolism
A04 - Antiemetics and antinauseants
A04A - Antiemetics and antinauseants
A04AD - Other antiemetics
A04AD11 - Nabilone
Absorption
Nabilone appears to be completely absorbed from the human gastrointestinal tract when administered orally. Following oral administration of a 2 mg dose of radiolabeled nabilone, peak plasma concentrations of approximately 2 ng/mL nabilone and 10 ng equivalents/mL total radioactivity are achieved within 2.0 hours.
Route of Elimination
The route and rate of the elimination of nabilone and its metabolites are similar to those observed with other cannabinoids, including delta-9-THC (dronabinol). When nabilone is administered intravenously, the drug and its metabolites are eliminated mainly in the feces (approximately 67%) and to a lesser extent in the urine (approximately 22%) within 7 days. Of the 67% recovered from the feces, 5% corresponded to the parent compound and 16% to its carbinol metabolite. Following oral administration about 60% of nabilone and its metabolites were recovered in the feces and about 24% in urine. Therefore, it appears that the major excretory pathway is the biliary system.
Volume of Distribution
The apparent volume of distribution of nabilone is about 12.5 L/kg.
Hepatic. Two metabolic pathways have been suggested. The major pathway probably involves the direct oxidation of Nabilone to produce hydroxylic and carboxylic analogues. These compounds are thought to account for the remaining plasma radioactivity when carbinol metabolites have been extracted.
The plasma half-life (T1/2) values for nabilone and total radioactivity of identified and unidentified metabolites are about 2 and 35 hours, respectively.
Nabilone is an orally active synthetic cannabinoid which, like other cannabinoids, has complex effects on the central nervous system (CNS). It has been suggested that the antiemetic effect of nabilone is caused by interaction with the cannabinoid receptor system, i.e., the CB (1) receptor, which is a component of the endocannabinoid system of the body. The endocannabinoid system is widely distributed throughout the central and peripheral nervous system (via the Cannabinoid Receptors CB1 and CB2) and plays a role in many physiological processes such as inflammation, cardiovascular function, learning, pain, memory, stress and emotional regulation, and the sleep/wake cycle among many others. CB1 receptors are found in both the central and peripheral nervous system, and are most abundant in the hippocampus and amygdala, which are the areas of the brain responsible for short-term memory storage and emotional regulation. CB2 receptors are mainly located in the peripheral nervous system and can be found on lymphoid tissue where they are involved in regulation of immune function.
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