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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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ABOUT THIS PAGE

Looking for 51022-71-0 / Nabilone API manufacturers, exporters & distributors?

Nabilone manufacturers, exporters & distributors 1

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API | Excipient name

Nabilone

Synonyms

51022-71-0, Cesamet, Chembl947, Lilly 109514, 2n4o9l084n, Cpd 109514

Cas Number

51022-71-0

Unique Ingredient Identifier (UNII)

2N4O9L084N

About 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 Manufacturers

A Nabilone manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Nabilone, including repackagers and relabelers. The FDA regulates Nabilone manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Nabilone API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

click here to find a list of Nabilone manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

Nabilone Suppliers

A Nabilone supplier is an individual or a company that provides Nabilone active pharmaceutical ingredient (API) or Nabilone finished formulations upon request. The Nabilone suppliers may include Nabilone API manufacturers, exporters, distributors and traders.

click here to find a list of Nabilone suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Nabilone USDMF

A Nabilone DMF (Drug Master File) is a document detailing the whole manufacturing process of Nabilone active pharmaceutical ingredient (API) in detail. Different forms of Nabilone DMFs exist exist since differing nations have different regulations, such as Nabilone USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Nabilone DMF submitted to regulatory agencies in the US is known as a USDMF. Nabilone USDMF includes data on Nabilone's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Nabilone USDMF is kept confidential to protect the manufacturer’s intellectual property.

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Nabilone NDC

National Drug Code is a comprehensive database maintained by the FDA that contains information on all drugs marketed in the US. This directory includes information about finished drug products, unfinished drug products, and compounded drug products, including those containing Nabilone as an active pharmaceutical ingredient (API).

Finished drug products

The FDA updates the NDC directory daily. The NDC numbers for Nabilone API and other APIs are published in this directory by the FDA.

Unfinished drugs

The NDC unfinished drugs database includes product listing information submitted for all unfinished drugs, such as active pharmaceutical ingredients (APIs), drugs intended for further processing and bulk drug substances for compounding.

Pharmaceutical companies that manufacture Nabilone as an active pharmaceutical ingredient (API) must furnish the FDA with an updated record of all drugs that they produce, prepare, propagate, compound, or process for commercial distribution in the US at their facilities.

Compounded drug products

The NDC directory also contains data on finished compounded human drug products that contain Nabilone and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a Nabilone NDC to their finished compounded human drug products, they may choose to do so.

click here to find a list of Nabilone suppliers with NDC on PharmaCompass.

Nabilone GMP

Nabilone Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Nabilone GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Nabilone GMP manufacturer or Nabilone GMP API supplier for your needs.

Nabilone CoA

A Nabilone CoA (Certificate of Analysis) is a formal document that attests to Nabilone's compliance with Nabilone specifications and serves as a tool for batch-level quality control.

Nabilone CoA mostly includes findings from lab analyses of a specific batch. For each Nabilone CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Nabilone may be tested according to a variety of international standards, such as European Pharmacopoeia (Nabilone EP), Nabilone JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Nabilone USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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