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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 the Company : Veranova is a global leader in the development and manufacturing of specialist and complex APIs for pharma and biotech customers. We have over 50 years of experience navigating the...

    Veranova is a global leader in the development and manufacturing of specialist and complex APIs for pharma and biotech customers. We have over 50 years of experience navigating the challenges of the global healthcare industry, and nurturing long-standing, trusted customer relationships. Operating within two divisions, Generics and Originators, we deliver a differentiated service offering to pharma and biotech customers for every stage in the drug development lifecycle. Macfarlan Smith Limited is trading as Veranova in the United Kingdom.
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    Nabilone

    About the Company : Founded in 1979, Noramco specializes in the development and manufacturing of APIs for both opioid and non-opioid products. With expertise in controlled substance development and ma...

    Founded in 1979, Noramco specializes in the development and manufacturing of APIs for both opioid and non-opioid products. With expertise in controlled substance development and manufacturing, Noramco offers services like supply-chain integration for high-purity controlled substances, efficient routes to APIs, analytical data, stability studies, regulatory help, formulation-friendly particle size grades, extended technical packages, DEA-compliant security and production capacity from kilos to multi-ton supply. Noramco also offers world-class supply security for controlled substances, from Schedule I to Schedule III.
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    Apotex Pharmachem

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    Nabilone

    About the Company : Apotex Pharmachem is a global fully integrated API R&D and manufacturing organization with its headquarters located in Brantford, Ontario, Canada and is a member of the Apotex grou...

    Apotex Pharmachem is a global fully integrated API R&D and manufacturing organization with its headquarters located in Brantford, Ontario, Canada and is a member of the Apotex group of companies. Currently employing more than 1600 highly-skilled and motivated professionals globally, Apotex Pharmachem has multiple facilities around the world located in Canada, India, Mexico, and China.
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    About the Company : CPL Sachse is a contract development and manufacturing organization specializing in the production of organic pharmaceutical active ingredients for both human and veterinary medica...

    CPL Sachse is a contract development and manufacturing organization specializing in the production of organic pharmaceutical active ingredients for both human and veterinary medical applications. Our manufacturing processes adhere to current Good Manufacturing Practices (cGMP) as outlined in the EU GMP Guide Part II (ICH Q7). We undergo regular monitoring by the relevant local authority, which issues us GMP certificates specifically for our active ingredients.
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    Nabilone

    About the Company : Optimus is one of the fastest-growing pharmaceutical companies with 16 years of experience in providing the best quality of API, Intermediates & Finished formulations in Global mar...

    Optimus is one of the fastest-growing pharmaceutical companies with 16 years of experience in providing the best quality of API, Intermediates & Finished formulations in Global markets. Our aim from day one has been to provide and ensure better healthcare across the globe through our research, Innovations, affordable products & manufacturing excellence. Optimus was established to provide quality & affordable pharmaceutical products in the global markets.
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    ABOUT THIS PAGE

    Cesamet Manufacturers

    A Cesamet manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Cesamet, including repackagers and relabelers. The FDA regulates Cesamet manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Cesamet 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 Cesamet manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

    Cesamet Suppliers

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

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

    Cesamet USDMF

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

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

    click here to find a list of Cesamet suppliers with USDMF on PharmaCompass.

    Cesamet 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 Cesamet as an active pharmaceutical ingredient (API).

    Finished drug products

    The FDA updates the NDC directory daily. The NDC numbers for Cesamet 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 Cesamet 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 Cesamet and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a Cesamet NDC to their finished compounded human drug products, they may choose to do so.

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

    Cesamet GMP

    Cesamet 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 Cesamet 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 Cesamet GMP manufacturer or Cesamet GMP API supplier for your needs.

    Cesamet CoA

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

    Cesamet CoA mostly includes findings from lab analyses of a specific batch. For each Cesamet 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.

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