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Chemistry

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Also known as: 51022-71-0, Cesamet, Chembl947, Lilly 109514, 2n4o9l084n, Cpd 109514
Molecular Formula
C24H36O3
Molecular Weight
372.5  g/mol
InChI Key
GECBBEABIDMGGL-RTBURBONSA-N
FDA UNII
2N4O9L084N

Nabilone
Nabilone is a synthetic cannabinoid and dibenzopyrane derivative with anti-emetic activity. Although the mechanism of action has not been fully elucidated yet, it has been suggested that nabilone is a highly selective and strong agonist for the cannabinoid receptors CB1 and CB2, both of which are coupled to Gi/o proteins. The CB1 receptors are expressed predominantly in central and peripheral neurons and receptor stimulation has been implicated in the reduction of chemotherapy-induced nausea.
Nabilone is a Cannabinoid.
1 2D Structure

Nabilone

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(6aR,10aR)-1-hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-7,8,10,10a-tetrahydro-6aH-benzo[c]chromen-9-one
2.1.2 InChI
InChI=1S/C24H36O3/c1-6-7-8-9-12-23(2,3)16-13-20(26)22-18-15-17(25)10-11-19(18)24(4,5)27-21(22)14-16/h13-14,18-19,26H,6-12,15H2,1-5H3/t18-,19-/m1/s1
2.1.3 InChI Key
GECBBEABIDMGGL-RTBURBONSA-N
2.1.4 Canonical SMILES
CCCCCCC(C)(C)C1=CC(=C2C3CC(=O)CCC3C(OC2=C1)(C)C)O
2.1.5 Isomeric SMILES
CCCCCCC(C)(C)C1=CC(=C2[C@@H]3CC(=O)CC[C@H]3C(OC2=C1)(C)C)O
2.2 Other Identifiers
2.2.1 UNII
2N4O9L084N
2.3 Synonyms
2.3.1 MeSH Synonyms

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

2.3.2 Depositor-Supplied Synonyms

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

2.4 Create Date
2005-11-20
3 Chemical and Physical Properties
Molecular Weight 372.5 g/mol
Molecular Formula C24H36O3
XLogP36.4
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count6
Exact Mass372.26644501 g/mol
Monoisotopic Mass372.26644501 g/mol
Topological Polar Surface Area46.5 Ų
Heavy Atom Count27
Formal Charge0
Complexity524
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameCesamet
PubMed HealthNabilone (By mouth)
Drug ClassesAntiemetic
Drug LabelCesamet (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 IngredientNabilone
Dosage FormCapsule
RouteOral
Strength1mg
Market StatusPrescription
CompanyMeda Pharms

2 of 2  
Drug NameCesamet
PubMed HealthNabilone (By mouth)
Drug ClassesAntiemetic
Drug LabelCesamet (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 IngredientNabilone
Dosage FormCapsule
RouteOral
Strength1mg
Market StatusPrescription
CompanyMeda Pharms

4.2 Drug Indication

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


5 Pharmacology and Biochemistry
5.1 Pharmacology

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.


5.2 MeSH Pharmacological Classification

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.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
NABILONE
5.3.2 FDA UNII
2N4O9L084N
5.3.3 Pharmacological Classes
Cannabinoids [CS]; Cannabinoid [EPC]
5.4 ATC Code

A - Alimentary tract and metabolism

A04 - Antiemetics and antinauseants

A04A - Antiemetics and antinauseants

A04AD - Other antiemetics

A04AD11 - Nabilone


5.5 Absorption, Distribution and Excretion

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.


5.6 Metabolism/Metabolites

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.


5.7 Biological Half-Life

The plasma half-life (T1/2) values for nabilone and total radioactivity of identified and unidentified metabolites are about 2 and 35 hours, respectively.


5.8 Mechanism of Action

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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