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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
(-)-delta9-trans-TetrahydrocannabinolNot AvailableNot Available
1-trans-delta-9-TetrahydrocannabinolNot AvailableNot Available
3-Pentyl-6,6,9-trimethyl-6a,7,8,10a-tetrahydro-6H-dibenzo(b,D)pyran-1-olNot AvailableNot Available
6,6,9-Trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-olNot AvailableNot Available
delta-9-tetrahydrocannabinolNot AvailableNot Available
delta-9-THCNot AvailableNot Available
delta(1)-TetrahydrocannabinolNot AvailableNot Available
delta(9)-THCNot AvailableNot Available
delta9-TetrahydrocannabinolNot AvailableNot Available
DronabinolNot 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 KeyCYQFCXCEBYINGO-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
Not Available
8,11-Dihydroxy-delta-9-THCDetails
11-Hydroxy-delta-9-THC
Not Available
8,11-Dihydroxy-delta-9-THCDetails
11-Hydroxy-delta-9-THC
Not Available
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.

Targets

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

Enzymes

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

Transporters

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

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