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Identification
NameDronabinol
Accession NumberDB00470  (APRD00571)
Typesmall molecule
Groupsapproved, illicit
Description

A psychoactive compound extracted from the resin of Cannabis sativa (marihuana, hashish). The isomer delta-9-tetrahydrocannabinol (THC) is considered the most active form, producing characteristic mood and perceptual changes associated with this compound. Dronabinol is a synthetic form of delta-9-THC. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
1-trans-delta-9-TetrahydrocannabinolNot AvailableNot Available
delta-9-tetrahydrocannabinolNot AvailableNot Available
delta-9-THCNot AvailableNot Available
DronabinolumLatinNot Available
TetrahydrocannabinolNot AvailableNot Available
Δ9-tetrahydrocannabinolNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
MarinolNot Available
Brand mixturesNot Available
Categories
CAS number1972-08-3
WeightAverage: 314.4617
Monoisotopic: 314.224580204
Chemical FormulaC21H30O2
InChI KeyInChIKey=CYQFCXCEBYINGO-IAGOWNOFSA-N
InChI
InChI=1S/C21H30O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h11-13,16-17,22H,5-10H2,1-4H3/t16-,17-/m1/s1
IUPAC Name
(6aR,10aR)-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromen-1-ol
SMILES
[H][C@@]12C=C(C)CC[C@@]1([H])C(C)(C)OC1=C2C(O)=CC(CCCCC)=C1
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassNaphthopyrans
SubclassNot Available
Direct parentNaphthopyrans
Alternative parentsBenzopyrans; Phenols and Derivatives; Alkyl Aryl Ethers; Enols; Polyamines
Substituentschromane; benzopyran; phenol derivative; alkyl aryl ether; benzene; enol; polyamine; ether
Classification descriptionThis compound belongs to the naphthopyrans. These are compounds containing a pyran ring fused to a naphthalene moeity.
Pharmacology
IndicationFor the treatment of anorexia associated with weight loss in patients with AIDS, and nausea and vomiting associated with cancer chemotherapy in patients who have failed to respond adequately to conventional antiemetic treatments
PharmacodynamicsMarinol may has complex effects on the central nervous system (CNS), including cannabinoid receptors. Dronabinol may inhibit endorphins in the emetic center, suppress prostaglandin synthesis, and/or inhibit medullary activity through an unspecified cortical action.
Mechanism of actionThe mechanism of action of marinol is not completely understood. It is thought that cannabinoid receptors in neural tissues may mediate the effects of dronabinol and other cannabinoids. Animal studies with other cannabinoids suggest that marinol's antiemetic effects may be due to inhibition of the vomiting control mechanism in the medulla oblongata.
Absorption90 - 95%
Volume of distribution
  • 10 L/kg
Protein binding97%
Metabolism

Hepatic

SubstrateEnzymesProduct
Dronabinol
11-Hydroxy-delta-9-THCDetails
Dronabinol
7-beta-Hydroxy-delta-9-THCDetails
Dronabinol
7-alpha-Hydroxy-delta-9-THCDetails
Dronabinol
8-Hydroxy-delta-9-THCDetails
Dronabinol
8-beta-Hydroxy-delta-9-THCDetails
Dronabinol
9-alpha,10-alpha-epoxyhexahydrocannabinolDetails
8-Hydroxy-delta-9-THC
    8,11-Dihydroxy-delta-9-THCDetails
    11-Hydroxy-delta-9-THC
      8,11-Dihydroxy-delta-9-THCDetails
      11-Hydroxy-delta-9-THC
        11-Nor-9-carboxy-delta-9-THCDetails
        Route of eliminationDronabinol and its biotransformation products are excreted in both feces and urine.
        Half lifeAlpha phase: approximately 4 hours; Beta phase: 25-36 hours
        Clearance
        • 0.2 L/kg-hr
        ToxicityNot Available
        Affected organisms
        • Humans and other mammals
        PathwaysNot Available
        SNP Mediated EffectsNot Available
        SNP Mediated Adverse Drug ReactionsNot Available
        ADMET
        Predicted ADMET features
        Property Value Probability
        Human Intestinal Absorption + 0.9949
        Blood Brain Barrier + 0.9685
        Caco-2 permeable + 0.7607
        P-glycoprotein substrate Substrate 0.8458
        P-glycoprotein inhibitor I Non-inhibitor 0.5548
        P-glycoprotein inhibitor II Inhibitor 0.7191
        Renal organic cation transporter Non-inhibitor 0.8169
        CYP450 2C9 substrate Non-substrate 0.7522
        CYP450 2D6 substrate Non-substrate 0.9116
        CYP450 3A4 substrate Substrate 0.7199
        CYP450 1A2 substrate Inhibitor 0.6567
        CYP450 2C9 substrate Inhibitor 0.5352
        CYP450 2D6 substrate Non-inhibitor 0.7307
        CYP450 2C19 substrate Inhibitor 0.7683
        CYP450 3A4 substrate Non-inhibitor 0.6771
        CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.8349
        Ames test Non AMES toxic 0.9132
        Carcinogenicity Non-carcinogens 0.8947
        Biodegradation Not ready biodegradable 0.9725
        Rat acute toxicity 2.5940 LD50, mol/kg Not applicable
        hERG inhibition (predictor I) Weak inhibitor 0.7714
        hERG inhibition (predictor II) Non-inhibitor 0.8136
        Pharmacoeconomics
        Manufacturers
        • Svc pharma lp
        • Abbott products inc
        • Roxane Laboratories,Inc.
        Packagers
        Dosage forms
        FormRouteStrength
        CapsuleOral
        Prices
        Unit descriptionCostUnit
        Marinol 10 mg capsule29.86USDcapsule
        Dronabinol 10 mg capsule19.26USDcapsule
        Marinol 5 mg capsule16.0USDcapsule
        Dronabinol 5 mg capsule11.8USDcapsule
        Marinol 2.5 mg capsule8.02USDcapsule
        Dronabinol 2.5 mg capsule5.11USDcapsule
        DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
        Patents
        CountryPatent NumberApprovedExpires (estimated)
        United States67034181994-02-262011-02-26
        Properties
        Statesolid
        Experimental Properties
        PropertyValueSource
        melting point200 °C at 2.00E-02 mm HgNot Available
        water solubility2800 mg/L (at 23 °C)NIH NTP Reports web-site
        logP5.648Not Available
        pKa10.6PHYSICIAN'S DESK REFERENCE (1998)
        Predicted Properties
        PropertyValueSource
        water solubility2.63e-03 g/lALOGPS
        logP7.29ALOGPS
        logP5.94ChemAxon
        logS-5.1ALOGPS
        pKa (strongest acidic)9.34ChemAxon
        pKa (strongest basic)-4.9ChemAxon
        physiological charge0ChemAxon
        hydrogen acceptor count2ChemAxon
        hydrogen donor count1ChemAxon
        polar surface area29.46ChemAxon
        rotatable bond count4ChemAxon
        refractivity96.73ChemAxon
        polarizability38.96ChemAxon
        number of rings3ChemAxon
        bioavailability1ChemAxon
        rule of fiveNoChemAxon
        Ghose filterNoChemAxon
        Veber's ruleYesChemAxon
        MDDR-like ruleNoChemAxon
        Spectra
        SpectraNot Available
        References
        Synthesis Reference

        Fabio E.S. SOUZA, Jason E. FIELD, Ming PAN, “INTERMEDIATE COMPOUNDS IN THE SYNTHESIS OF DRONABINOL.” U.S. Patent US20080312465, issued December 18, 2008.

        US20080312465
        General ReferenceNot Available
        External Links
        ResourceLink
        KEGG DrugD00306
        KEGG CompoundC06972
        BindingDB50007391
        Therapeutic Targets DatabaseDAP000207
        PharmGKBPA449421
        IUPHAR2424
        Guide to Pharmacology2424
        Drug Product Database611204
        RxListhttp://www.rxlist.com/cgi/generic2/drona.htm
        WikipediaMarinol
        ATC CodesA04AD10
        AHFS Codes
        • 56:22.92
        PDB EntriesNot Available
        FDA labelNot Available
        MSDSshow(51.4 KB)
        Interactions
        Drug Interactions
        Drug
        TrimethobenzamideAnticholinergics, such as Trimethobenzamide, may increase the tachycardic effect of cannabinoids such as Marinol. Close monitoring of cardiovascular effects is recommended.
        TrospiumAnticholinergics, such as Trospium, may increase the tachycardic effect of cannabinoids such as Marinol. Close monitoring of cardiovascular effects is recommended.
        Food Interactions
        • Avoid alcohol.
        • Take without regard to meals.

        1. Cannabinoid receptor 1

        Kind: protein

        Organism: Human

        Pharmacological action: yes

        Actions: agonist

        Components

        Name UniProt ID Details
        Cannabinoid receptor 1 P21554 Details

        References:

        1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
        2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
        3. Pryce G, Giovannoni G, Baker D: Mifepristone or inhibition of 11beta-hydroxylase activity potentiates the sedating effects of the cannabinoid receptor-1 agonist Delta(9)-tetrahydrocannabinol in mice. Neurosci Lett. 2003 May 1;341(2):164-6. Pubmed
        4. Tsai SJ, Wang YC, Hong CJ: Association study of a cannabinoid receptor gene (CNR1) polymorphism and schizophrenia. Psychiatr Genet. 2000 Sep;10(3):149-51. Pubmed
        5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

        2. Cannabinoid receptor 2

        Kind: protein

        Organism: Human

        Pharmacological action: unknown

        Actions: agonist

        Components

        Name UniProt ID Details
        Cannabinoid receptor 2 P34972 Details

        References:

        1. Davis M, Maida V, Daeninck P, Pergolizzi J: The emerging role of cannabinoid neuromodulators in symptom management. Support Care Cancer. 2007 Jan;15(1):63-71. Epub 2006 Dec 1. Pubmed
        2. Pertwee RG: Emerging strategies for exploiting cannabinoid receptor agonists as medicines. Br J Pharmacol. 2009 Feb;156(3):397-411. Pubmed

        1. Cytochrome P450 3A4

        Kind: protein

        Organism: Human

        Pharmacological action: unknown

        Actions: substrate

        Components

        Name UniProt ID Details
        Cytochrome P450 3A4 P08684 Details

        References:

        1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. Pubmed

        2. Cytochrome P450 2C9

        Kind: protein

        Organism: Human

        Pharmacological action: unknown

        Actions: substrate

        Components

        Name UniProt ID Details
        Cytochrome P450 2C9 P11712 Details

        References:

        1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. Pubmed
        2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

        3. Cytochrome P450 2C19

        Kind: protein

        Organism: Human

        Pharmacological action: unknown

        Actions: substrate

        Components

        Name UniProt ID Details
        Cytochrome P450 2C19 P33261 Details

        References:

        1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. Pubmed
        2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

        4. Prostaglandin G/H synthase 1

        Kind: protein

        Organism: Human

        Pharmacological action: unknown

        Actions: substrate

        Components

        Name UniProt ID Details
        Prostaglandin G/H synthase 1 P23219 Details

        References:

        1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. Pubmed

        5. Cytochrome P450 1A1

        Kind: protein

        Organism: Human

        Pharmacological action: unknown

        Actions: substrate

        Components

        Name UniProt ID Details
        Cytochrome P450 1A1 P04798 Details

        References:

        1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

        6. Cytochrome P450 2A6

        Kind: protein

        Organism: Human

        Pharmacological action: unknown

        Actions: substrate

        Components

        Name UniProt ID Details
        Cytochrome P450 2A6 P11509 Details

        References:

        1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

        1. Multidrug resistance protein 1

        Kind: protein

        Organism: Human

        Pharmacological action: unknown

        Actions: inhibitor

        Components

        Name UniProt ID Details
        Multidrug resistance protein 1 P08183 Details

        References:

        1. Tournier N, Chevillard L, Megarbane B, Pirnay S, Scherrmann JM, Decleves X: Interaction of drugs of abuse and maintenance treatments with human P-glycoprotein (ABCB1) and breast cancer resistance protein (ABCG2). Int J Neuropsychopharmacol. 2010 Aug;13(7):905-15. Epub 2009 Nov 4. Pubmed

        2. ATP-binding cassette sub-family G member 2

        Kind: protein

        Organism: Human

        Pharmacological action: unknown

        Actions: inhibitor

        Components

        Name UniProt ID Details
        ATP-binding cassette sub-family G member 2 Q9UNQ0 Details

        References:

        1. Tournier N, Chevillard L, Megarbane B, Pirnay S, Scherrmann JM, Decleves X: Interaction of drugs of abuse and maintenance treatments with human P-glycoprotein (ABCB1) and breast cancer resistance protein (ABCG2). Int J Neuropsychopharmacol. 2010 Aug;13(7):905-15. Epub 2009 Nov 4. Pubmed

        Comments
        Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:10