Identification

Name
Dronabinol
Accession Number
DB00470  (APRD00571)
Type
Small Molecule
Groups
Approved, Illicit
Description

Dronabinol (marketed as Marinol) is a synthetic form of delta-9-tetrahydrocannabinol (Δ⁹-THC), the primary psychoactive component of cannabis (marijuana). THC demonstrates its effects through weak partial agonist activity at Cannabinoid-1 (CB1R) and Cannabinoid-2 (CB2R) receptors, which results in the well-known effects of smoking cannabis such as increased appetite, reduced pain, and changes in emotional and cognitive processes. Due to its evidence as an appetite stimulant and an anti-nauseant, Dronabinol is approved for use in anorexia associated with weight loss in patients with AIDS and for the treatment of nausea and vomiting associated with cancer chemotherapy in patients who have failed to respond adequately to conventional antiemetic treatments [Label].

Tetrahydrocannabinol (THC) and cannabidiol (CBD) are the two most abundant cannabinoids found naturally in the resin of the marijuana plant, both of which are pharmacologically active due to their interaction with cannabinoid receptors that are found throughout the body [4]. While both CBD and THC are used for medicinal purposes, they have different receptor activity, function, and physiological effects. If not provided in their activated form (such as through synthetic forms like Dronabinol or Nabilone), THC and CBD are obtained through conversion from their precursors, tetrahydrocannabinolic acid-A (THCA-A) and cannabidiolic acid (CBDA), through decarboxylation reactions. This can be achieved through heating, smoking, vaporization, or baking of dried unfertilized female cannabis flowers.

From a pharmacological perspective, Cannabis' diverse receptor profile explains its potential application for such a wide variety of medical conditions. Cannabis contains more than 400 different chemical compounds, of which 61 are considered cannabinoids, a class of compounds that act upon endogenous cannabinoid receptors of the body [1]. 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 [2]. 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 [3].

Structure
Thumb
Synonyms
  • (-)-delta9-trans-Tetrahydrocannabinol
  • 1-trans-delta-9-Tetrahydrocannabinol
  • 3-Pentyl-6,6,9-trimethyl-6a,7,8,10a-tetrahydro-6H-dibenzo(b,D)pyran-1-ol
  • 6,6,9-Trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol
  • delta-9-tetrahydrocannabinol
  • delta-9-THC
  • delta(1)-Tetrahydrocannabinol
  • delta(9)-THC
  • delta9-Tetrahydrocannabinol
  • Dronabinol
  • Dronabinolum
  • Tetrahydrocannabinol
  • Δ9-tetrahydrocannabinol
External IDs
Abbott 40566 / ABBOTT-40566 / Dea No. 7369 / Dea No. 7370 / J882F / NSC-134454 / QCD 84924 / QCD-84924 / SP 104 / SP-104
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
DronabinolCapsule2.5 mg/1OralAscend Laboratories, LLC2017-05-10Not applicableUs
DronabinolCapsule5 mg/1OralActavis Pharma, Inc.2005-06-072019-05-31Us
DronabinolCapsule10 mg/1OralAscend Laboratories, LLC2017-05-10Not applicableUs
DronabinolCapsule10 mg/1OralActavis Pharma, Inc.1994-08-112019-09-30Us
DronabinolCapsule5 mg/1OralAscend Laboratories, LLC2017-05-10Not applicableUs
DronabinolCapsule2.5 mg/1OralActavis Pharma, Inc.1994-08-112019-05-31Us
MarinolCapsule5 mgOralAbbott1994-12-312012-02-24Canada
MarinolCapsule2.5 mgOralAbbott1994-12-312012-02-24Canada
MarinolCapsule2.5 mg/1OralPhysicians Total Care, Inc.1994-08-112014-03-31Us
MarinolCapsule5 mg/1OralAbbVie Inc.2010-07-13Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
DronabinolCapsule5 mg/1OralPhysicians Total Care, Inc.2008-08-19Not applicableUs
DronabinolCapsule10 mg/1OralAkorn2014-06-20Not applicableUs
DronabinolCapsule2.5 mg/1OralLannett Company, Inc.2018-05-18Not applicableUs
DronabinolCapsule5 mg/1OralRhodes Pharmaceuticals L.P.2018-06-26Not applicableUs
DronabinolCapsule5 mg/1OralPar Pharmaceutical2008-06-27Not applicableUs
DronabinolCapsule10 mg/1OralLannett Company, Inc.2018-05-18Not applicableUs
DronabinolCapsule2.5 mg/1OralAmerican Health Packaging2018-07-16Not applicableUs
DronabinolCapsule, liquid filled5 mg/1OralMylan Pharmaceuticals2011-11-012016-06-30Us
DronabinolCapsule2.5 mg/1OralMajor Pharmaceuticals2018-06-26Not applicableUs
DronabinolCapsule2.5 mg/1OralAkorn2014-06-20Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
SativexDronabinol (27 mg) + Cannabidiol (25 mg)SprayBuccalGw Pharma Limited2005-06-22Not applicableCanada
Categories
UNII
7J8897W37S
CAS number
1972-08-3
Weight
Average: 314.4617
Monoisotopic: 314.224580204
Chemical Formula
C21H30O2
InChI Key
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

Pharmacology

Indication

For 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

Associated Conditions
Pharmacodynamics

Marinol 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 action

Dronabinol is a synthetic form of delta-9-tetrahydrocannabinol (Δ⁹-THC), the primary psychoactive component of cannabis (marijuana). THC demonstrates its effects through weak partial agonist activity at Cannabinoid-1 (CB1R) and Cannabinoid-2 (CB2R) receptors, which results in the well-known effects of smoking cannabis such as increased appetite, reduced pain, and changes in emotional and cognitive processes.

TargetActionsOrganism
ACannabinoid receptor 1
agonist
Human
UCannabinoid receptor 2
agonist
Human
Absorption

Dronabinol capsules are almost completely absorbed (90 to 95%) after single oral doses. Due to the combined effects of first pass hepatic metabolism and high lipid solubility, only 10 to 20% of the administered dose reaches the systemic circulation. After oral administration, dronabinol has an onset of action of approximately 0.5 to 1 hours and peak effect at 2 to 4 hours. Following BID dosing of 2.5mg of dronabinol, Cmax was found to be 1.32ng/mL with a median Tmax of 1.00 hr.

Volume of distribution

Dronabinol has a large apparent volume of distribution, approximately 10 L/kg, because of its lipid solubility.

Protein binding

The plasma protein binding of dronabinol and its metabolites is approximately 97%.

Metabolism

THC is primarily metabolized in the liver by microsomal hydroxylation and oxidation reactions catalyzed by Cytochrome P450 enzymes. 11-hydroxy-▵9-tetrahydrocannabinol (11-OH-THC) is the primary active metabolite, capable of producing psychological and behavioural effects, which is then metabolized into 11-nor-9-carboxy-▵ 9-tetrahydrocannabinol (THC-COOH), THC's primary inactive metabolite [1]. Dronabinol and its principal active metabolite, 11-OH-delta-9-THC, are present in approximately equal concentrations in plasma. Concentrations of both parent drug and metabolite peak at approximately 0.5 to 4 hours after oral dosing and decline over several days [Label].

Route of elimination

Dronabinol and its biotransformation products are excreted in both feces and urine. Because of its large volume of distribution, dronabinol and its metabolites may be excreted at low levels for prolonged periods of time. Following single dose administration, low levels of dronabinol metabolites have been detected for more than 5 weeks in the urine and feces.

Half life

The elimination phase of dronabinol can be described using a two compartment model with an initial (alpha) half-life of about 4 hours and a terminal (beta) half-life of 25 to 36 hours.

Clearance

Values for clearance average about 0.2 L/kg-hr, but are highly variable due to the complexity of cannabinoid distribution.

Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Cytochrome P450 2C9CYP2C9*2Not Available430C>TEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C9CYP2C9*3Not Available1075A>CEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C9CYP2C9*4Not Available1076T>CEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C9CYP2C9*5Not Available1080C>GEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C9CYP2C9*8Not Available449G>AEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C9CYP2C9*11Not Available1003C>TEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C9CYP2C9*12Not Available1465C>TEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C9CYP2C9*13Not Available269T>CEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C9CYP2C9*14Not Available374G>AEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C9CYP2C9*16Not Available895A>GEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C9CYP2C9*18Not Available1075A>C / 1190A>C  … show all Effect InferredPoor drug metabolizer.Details
Cytochrome P450 2C9CYP2C9*26Not Available389C>GEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C9CYP2C9*28Not Available641A>TEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C9CYP2C9*30Not Available1429G>AEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C9CYP2C9*33Not Available395G>AEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C9CYP2C9*6Not Available818delAEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C9CYP2C9*15Not Available485C>AEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C9CYP2C9*25Not Available353_362delAGAAATGGAAEffect InferredPoor drug metabolizer.Details
Cytochrome P450 2C9CYP2C9*35Not Available374G>T / 430C>TEffect InferredPoor drug metabolizer.Details

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Dronabinol.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Dronabinol.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of Tachycardia can be increased when Dronabinol is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineDronabinol may increase the central nervous system depressant (CNS depressant) activities of 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineDronabinol may increase the central nervous system depressant (CNS depressant) activities of 3,4-Methylenedioxyamphetamine.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Dronabinol.
4-Bromo-2,5-dimethoxyamphetamineDronabinol may increase the central nervous system depressant (CNS depressant) activities of 4-Bromo-2,5-dimethoxyamphetamine.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Dronabinol.
4-MethoxyamphetamineDronabinol may increase the central nervous system depressant (CNS depressant) activities of 4-Methoxyamphetamine.
5-androstenedioneThe metabolism of 5-androstenedione can be decreased when combined with Dronabinol.
Food Interactions
  • Avoid alcohol.
  • Take without regard to meals.

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 References
  1. Sharma P, Murthy P, Bharath MM: Chemistry, metabolism, and toxicology of cannabis: clinical implications. Iran J Psychiatry. 2012 Fall;7(4):149-56. [PubMed:23408483]
  2. Baron EP: Comprehensive Review of Medicinal Marijuana, Cannabinoids, and Therapeutic Implications in Medicine and Headache: What a Long Strange Trip It's Been .... Headache. 2015 Jun;55(6):885-916. doi: 10.1111/head.12570. Epub 2015 May 25. [PubMed:26015168]
  3. Kaur R, Ambwani SR, Singh S: Endocannabinoid System: A Multi-Facet Therapeutic Target. Curr Clin Pharmacol. 2016;11(2):110-7. [PubMed:27086601]
  4. Elsohly MA, Slade D: Chemical constituents of marijuana: the complex mixture of natural cannabinoids. Life Sci. 2005 Dec 22;78(5):539-48. doi: 10.1016/j.lfs.2005.09.011. Epub 2005 Sep 30. [PubMed:16199061]
External Links
Human Metabolome Database
HMDB0014613
KEGG Drug
D00306
KEGG Compound
C06972
PubChem Compound
16078
PubChem Substance
46508472
ChemSpider
15266
BindingDB
60994
ChEBI
66964
ChEMBL
CHEMBL465
Therapeutic Targets Database
DAP000207
PharmGKB
PA449421
IUPHAR
2424
Guide to Pharmacology
GtP Drug Page
HET
TCI
RxList
RxList Drug Page
Wikipedia
Dronabinol
ATC Codes
A04AD10 — Dronabinol
AHFS Codes
  • 56:22.92 — Miscellaneous Antiemetics
PDB Entries
3ls4
FDA label
Download (414 KB)
MSDS
Download (51.4 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedBasic ScienceHealthy Volunteers1
0CompletedTreatmentCannabis / Marijuana Abuse1
0Not Yet RecruitingBasic ScienceCannabis / Marijuana / Sleep / THC1
0Not Yet RecruitingTreatmentBone Metastases / Cancer, Breast / Pain NOS1
0RecruitingTreatmentChronic Pain, Widespread1
1Active Not RecruitingBasic ScienceBipolar Disorder (BD) / Delta-9-Tetrahydroncannabinol / Healthy Controls1
1Active Not RecruitingBasic ScienceHealthy Volunteers3
1CompletedNot AvailableBioavailability1
1CompletedNot AvailableDrug Abuse, Medication1
1CompletedNot AvailableMarijuana Abuse1
1CompletedNot AvailableMarijuana Dependence1
1CompletedNot AvailableTo Determine Bioequivalence Under Fasting Conditions1
1CompletedBasic ScienceCannabis Use Disorders / Dual Diagnosis / Psychotic Disorder NOS / Schizoaffective Disorders / Schizophrenic Disorders1
1CompletedBasic ScienceEffects of Sativex on ECG1
1CompletedBasic ScienceEndocannabinoids / Magnetic Resonance Imaging (MRI) / Memory / Reward / Tetrahydrocannabinol1
1CompletedBasic ScienceEvaluation of Abuse Potential of Sativex1
1CompletedBasic ScienceEvaluation of Pharmacokinetics of Sativex in the Absence and Presence of a CYP2C19 Inhibitor / Evaluation of Pharmacokinetics of Sativex in the Absence and Presence of a Known Inducer of CYP3A4 / Evaluation of Pharmacokinetics of Sativex in the Absence and Presence of a Potent Inhibitor of CYP3A41
1CompletedBasic ScienceFood Effect1
1CompletedBasic ScienceHealthy Volunteers1
1CompletedBasic ScienceHealthy Volunteers / Modeling Psychosis1
1CompletedBasic SciencePain NOS1
1CompletedOtherCannabis / Cannabis Abuse / Dependence / FMRI / Pharmacokinetics1
1CompletedOtherHealthy Volunteers1
1CompletedTreatmentCachexia / HIV Wasting Syndrome / Human Immunodeficiency Virus (HIV) Infections1
1CompletedTreatmentDrug Safety1
1CompletedTreatmentHepatic Impairment1
1CompletedTreatmentNausea / Neoplasms, Brain / Vomiting1
1Not Yet RecruitingBasic ScienceHealthy Volunteers / Modeling Psychosis1
1RecruitingBasic ScienceCannabis2
1RecruitingBasic ScienceCannabis Use Disorders / Dual Diagnosis / Psychotic Disorder NOS / Schizophrenic Disorders1
1TerminatedBasic ScienceTo Provide Further Information About the Potential Need for Sativex Dose Adjustments in Patient Populations1
1TerminatedTreatmentHead and Neck Squamous Cell Carcinoma (HNSCC)1
1TerminatedTreatmentMarijuana Dependence1
1WithdrawnBasic ScienceImpaired Renal Function / Kidney Diseases1
1WithdrawnTreatmentCancer, Advanced1
1, 2CompletedBasic ScienceMarijuana Abuse1
1, 2CompletedBasic ScienceSmoking, Marijuana1
1, 2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
1, 2CompletedTreatmentMalignancies2
1, 2TerminatedNot AvailableSchizophrenic Disorders1
1, 2TerminatedTreatmentDisseminated Sclerosis1
2CompletedNot AvailableIrritable Bowel Syndrome (IBS)2
2CompletedBasic ScienceMarijuana Dependence1
2CompletedOtherMood / Pain NOS / Pain Threshold1
2CompletedSupportive CareMalignancies / Pain NOS / Palliative Care1
2CompletedTreatmentAbdominal Pain (AP) / Cannabinoid / Pancreatitis, Chronic / Tetrahydrocannabinol1
2CompletedTreatmentAbdominal Pain (AP) / Pain, Chronic / Pancreatitis, Chronic1
2CompletedTreatmentAbdominal Pain (AP) / Pain, Chronic / Postsurgical Pain1
2CompletedTreatmentAlzheimer Dementia (AD) / Behavioural Disturbances / Dementia, Vascular / Dementias / Pain NOS1
2CompletedTreatmentAnorexic / Malignancies / Olfactory Disorders / Taste Disorders1
2CompletedTreatmentCannabis Dependence1
2CompletedTreatmentHighly Active Antiretroviral Therapy (HAART)-Related Nausea and Vomiting / Human Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentHuntington's Disease (HD)1
2CompletedTreatmentMarijuana Abuse1
2CompletedTreatmentMarijuana Dependence1
2CompletedTreatmentObsessive Compulsive Disorder (OCD) / Trichotillomania1
2CompletedTreatmentSleep Apnea, Obstructive1
2Not Yet RecruitingTreatmentGilles de la Tourette's Syndrome1
2RecruitingTreatmentAlzheimer's Disease (AD)1
2RecruitingTreatmentBack Pain Lower Back / Cannabis / Pain, Neuropathic1
2RecruitingTreatmentFamilial Dysautonomia / Nausea / Vomiting1
2RecruitingTreatmentPain, Chronic1
2RecruitingTreatmentPosttraumatic Stress Disorders1
2Unknown StatusPreventionComplex Regional Pain Syndromes (CRPS) / CRP1
2Unknown StatusTreatmentCervical Dystonia1
2Unknown StatusTreatmentDisseminated Sclerosis1
2Unknown StatusTreatmentPain NOS1
2, 3CompletedSupportive CareAmyotrophic Lateral Sclerosis (ALS) / Motor Neurone Disease1
2, 3CompletedTreatmentCannabis Dependence / Marijuana Dependence1
2, 3CompletedTreatmentOpioid Dependence1
2, 3CompletedTreatmentPain, Chronic1
2, 3RecruitingTreatmentFeeling Anxious / Post-Operative Nausea and Vomiting (PONV) / Postoperative pain1
2, 3RecruitingTreatmentTrichotillomania1
2, 3TerminatedTreatmentCannabis Dependence / Marijuana Dependence1
2, 3WithdrawnBasic ScienceDisseminated Sclerosis1
3CompletedPreventionChemotherapy-Induced Nausea and Vomiting (CINV)1
3CompletedSupportive CareChemotherapy-Induced Nausea and Vomiting (CINV) / Unspecified Adult Solid Tumor, Protocol Specific1
3CompletedSupportive CareDetrusor Overactivity / Disseminated Sclerosis1
3CompletedSupportive CareDiabetic Neuropathies / Pain NOS1
3CompletedSupportive CareDisseminated Sclerosis / Spasticity3
3CompletedSupportive CareMalignancies / Pain NOS1
3CompletedSupportive CareMalignancies / Pain NOS / Palliative Care1
3CompletedSupportive CarePain NOS / Peripheral Neuropathy4
3CompletedTreatmentAnorexia Nervosa (AN)1
3CompletedTreatmentCancer, Advanced / Pain NOS4
3CompletedTreatmentCentral Neuropathic Pain in Multiple Sclerosis1
3CompletedTreatmentCerebral Palsy (CP)1
3CompletedTreatmentDisseminated Sclerosis5
3CompletedTreatmentDisseminated Sclerosis / Pain NOS1
3CompletedTreatmentDisseminated Sclerosis / Pain NOS / Spasticity1
3CompletedTreatmentDisseminated Sclerosis / Pain, Neuropathic1
3CompletedTreatmentDisseminated Sclerosis / Spasticity1
3CompletedTreatmentPain NOS2
3CompletedTreatmentPain, Neuropathic1
3RecruitingTreatmentGilles de la Tourette's Syndrome1
3WithdrawnSupportive CareDisseminated Sclerosis / Spasticity1
4CompletedBasic ScienceHealthy Participants1
4CompletedTreatmentDisseminated Sclerosis / Spasticity1
4CompletedTreatmentThoracic Pain1
4Not Yet RecruitingBasic ScienceAccident, Traffic / Alcohol Drinking / Cannabis1
4RecruitingBasic SciencePosttraumatic Stress Disorders1
4RecruitingDiagnosticIntoxication Alcohol / Intoxication Combined Alcohol THC / Intoxication THC1
4RecruitingTreatmentMedical Abortion / Pain NOS1
4SuspendedTreatmentEsophageal Diseases1
4Unknown StatusTreatmentPosttraumatic Stress Disorders1
Not AvailableActive Not RecruitingBasic ScienceAppetite Regulation1
Not AvailableCompletedNot AvailableDiabetes Mellitus (DM) / Disseminated Sclerosis / Malignancies / Pain, Neuropathic1
Not AvailableCompletedBasic ScienceHealthy Humans1
Not AvailableCompletedBasic ScienceHealthy Volunteers3
Not AvailableCompletedBasic SciencePsychomotor Impairment1
Not AvailableCompletedBasic ScienceSensory Science1
Not AvailableCompletedTreatmentAmyotrophic Lateral Sclerosis (ALS) / Muscle Cramps1
Not AvailableCompletedTreatmentCannabis Dependence1
Not AvailableCompletedTreatmentPost-Operative Nausea and Vomiting (PONV)1
Not AvailableRecruitingBasic SciencePost Traumatic Stress Disorder (PTSD)1
Not AvailableRecruitingTreatmentRehabilitation1
Not AvailableUnknown StatusBasic ScienceAttention Deficit Disorder With Hyperactivity (ADHD)1
Not AvailableUnknown StatusTreatmentFibromyalgia1

Pharmacoeconomics

Manufacturers
  • Svc pharma lp
  • Abbott products inc
  • Roxane Laboratories,Inc.
Packagers
  • Banner Pharmacaps Inc.
  • GW Pharma Ltd.
  • Par Pharmaceuticals
  • Pharmaceutics International Inc.
  • Physicians Total Care Inc.
  • Southwood Pharmaceuticals
  • UNIMED
  • Unimed Pharmaceuticals Inc.
  • Watson Pharmaceuticals
Dosage forms
FormRouteStrength
CapsuleOral10 mg/1
CapsuleOral5 mg/1
Capsule, liquid filledOral10 mg/1
Capsule, liquid filledOral2.5 mg/1
Capsule, liquid filledOral5 mg/1
CapsuleOral2.5 mg/1
CapsuleOral2.5 mg
CapsuleOral5 mg
CapsuleOral10 mg
SprayBuccal
SolutionOral5 mg/1mL
Prices
Unit descriptionCostUnit
Marinol 10 mg capsule29.86USD capsule
Dronabinol 10 mg capsule19.26USD capsule
Marinol 5 mg capsule16.0USD capsule
Dronabinol 5 mg capsule11.8USD capsule
Marinol 2.5 mg capsule8.02USD capsule
Dronabinol 2.5 mg capsule5.11USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6703418No2004-03-092011-02-26Us
US8222292No2012-07-172028-08-06Us
US9345771No2016-05-242028-08-06Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)200 °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 Solubility0.00263 mg/mLALOGPS
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 Area29.46 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity96.73 m3·mol-1ChemAxon
Polarizability38.96 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9949
Blood Brain Barrier+0.9685
Caco-2 permeable+0.7607
P-glycoprotein substrateSubstrate0.8458
P-glycoprotein inhibitor INon-inhibitor0.5548
P-glycoprotein inhibitor IIInhibitor0.7191
Renal organic cation transporterNon-inhibitor0.8169
CYP450 2C9 substrateNon-substrate0.7522
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.7199
CYP450 1A2 substrateInhibitor0.6567
CYP450 2C9 inhibitorInhibitor0.5352
CYP450 2D6 inhibitorNon-inhibitor0.7307
CYP450 2C19 inhibitorInhibitor0.7683
CYP450 3A4 inhibitorNon-inhibitor0.6771
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8349
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.8947
BiodegradationNot ready biodegradable0.9725
Rat acute toxicity2.5940 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7714
hERG inhibition (predictor II)Non-inhibitor0.8136
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-01pp-4792000000-06532e533cb7794b7c37
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzopyrans
Sub Class
1-benzopyrans
Direct Parent
2,2-dimethyl-1-benzopyrans
Alternative Parents
Alkyl aryl ethers / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Oxacyclic compounds / Hydrocarbon derivatives
Substituents
2,2-dimethyl-1-benzopyran / 1-hydroxy-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid / Alkyl aryl ether / Benzenoid / Oxacycle / Ether / Organic oxygen compound / Hydrocarbon derivative / Organooxygen compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
polyketide, diterpenoid, phytocannabinoid, benzochromene (CHEBI:66964) / Cannabinoids (C06972)

Targets

Details
1. Cannabinoid receptor 1
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Drug binding
Specific Function
Involved in cannabinoid-induced CNS effects. Acts by inhibiting adenylate cyclase. Could be a receptor for anandamide. Inhibits L-type Ca(2+) channel current. Isoform 2 and isoform 3 have altered l...
Gene Name
CNR1
Uniprot ID
P21554
Uniprot Name
Cannabinoid receptor 1
Molecular Weight
52857.365 Da
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:17139284]
  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:17016423]
  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:12686391]
  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:11204352]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Details
2. Cannabinoid receptor 2
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Agonist
General Function
Cannabinoid receptor activity
Specific Function
Heterotrimeric G protein-coupled receptor for endocannabinoid 2-arachidonoylglycerol mediating inhibition of adenylate cyclase. May function in inflammatory response, nociceptive transmission and b...
Gene Name
CNR2
Uniprot ID
P34972
Uniprot Name
Cannabinoid receptor 2
Molecular Weight
39680.275 Da
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:17139494]
  2. Pertwee RG: Emerging strategies for exploiting cannabinoid receptor agonists as medicines. Br J Pharmacol. 2009 Feb;156(3):397-411. doi: 10.1111/j.1476-5381.2008.00048.x. [PubMed:19226257]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
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:19515014]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
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:19515014]
  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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
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:19515014]
  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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...
Gene Name
PTGS1
Uniprot ID
P23219
Uniprot Name
Prostaglandin G/H synthase 1
Molecular Weight
68685.82 Da
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:19515014]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d 24-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
Molecular Weight
58164.815 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Const...
Gene Name
CYP2A6
Uniprot ID
P11509
Uniprot Name
Cytochrome P450 2A6
Molecular Weight
56501.005 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Bionorica Ethics Dronabinol Profile [File]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
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. doi: 10.1017/S1461145709990848. Epub 2009 Nov 4. [PubMed:19887017]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da
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. doi: 10.1017/S1461145709990848. Epub 2009 Nov 4. [PubMed:19887017]

Drug created on June 13, 2005 07:24 / Updated on December 12, 2018 07:05