Identification

Summary

Dronabinol is a synthetic delta-9-THC used in the treatment of anorexia and weight loss in HIV patients as well as nausea and vomiting in cancer chemotherapy.

Brand Names
Marinol, Sativex, Syndros
Generic Name
Dronabinol
DrugBank Accession Number
DB00470
Background

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.

Type
Small Molecule
Groups
Approved, Illicit
Structure
Weight
Average: 314.4617
Monoisotopic: 314.224580204
Chemical Formula
C21H30O2
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
  • THC
  • 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

Pharmacology

Indication

Dronabinol is indicated 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.8

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Associated Conditions
Contraindications & Blackbox Warnings
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Pharmacodynamics

Dronabinol-induced sympathomimetic activity may result in tachycardia and/or conjunctival injection. Its effects on blood pressure are inconsistent, but subjects have experienced orthostatic hypotension and/or syncope upon abrupt standing.8

Dronabinol also demonstrates reversible effects on appetite, mood, cognition, memory, and perception. These phenomena appear to be dose-related, increasing in frequency with higher dosages, and subject to great inter-patient variability. After oral administration, dronabinol capsules have an onset of action of approximately 0.5 to 1 hour and a peak effect at 2 to 4 hours. Duration of action for psychoactive effects is 4 to 6 hours, but the appetite stimulant effect of dronabinol may continue for 24 hours or longer after administration.8

Tachyphylaxis and tolerance develop to some of the cardiovascular and CNS pharmacologic effects of dronabinol with chronic use, suggesting an indirect effect on sympathetic neurons. In a study of the pharmacodynamics of chronic dronabinol exposure, healthy male subjects (N = 12) received 12 times the maximum dose for anorexia associated with weight loss in patients with AIDS of dronabinol capsules in divided doses for 16 days. An initial tachycardia induced by dronabinol was replaced successively by normal sinus rhythm and then bradycardia. A decrease in supine blood pressure, made worse by standing, was also observed initially. These subjects developed tolerance to the cardiovascular and subjective adverse CNS effects of dronabinol within 12 days of treatment initiation.8

Tachyphylaxis and tolerance do not appear to develop to the appetite stimulant effect of dronabinol. In clinical studies of dronabinol capsules in AIDS patients, at the recommended dosage, the appetite stimulant effect was sustained for up to five months.8

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
Humans
ACannabinoid receptor 2
agonist
Humans
Absorption

Dronabinol is almost completely absorbed (90 to 95%) after a single oral dose. Due to the combined effects of first-pass hepatic metabolism and high lipid solubility, only 10 to 20% of the administered dose reaches systemic circulation. Relative bioavailability data from healthy male and female subjects suggest that a dose of 4.2 mg of SYNDROS provides comparable systemic exposure (Cmax and AUC) to a 5 mg dronabinol capsule, under fasted conditions, with the Cmax and AUCinf of 1.9 ± 1.3 ng/mL and 3.8 ± 1.8 ng.h/mL respectively. The concentrations of both dronabinol and its major active metabolite (11-hydroxy-delta-9-THC) peak at approximately 0.5 to 4 hours after oral dosing with SYNDROS and decline over several days. The mean inter- and intra-subject variability in dronabinol pharmacokinetics (Cmax and AUCinf) was approximately 66% and 47% and 67% and 14%, respectively, following the administration of SYNDROS to healthy subjects.8

Volume of distribution

Dronabinol has a large apparent volume of distribution, approximately 10 L/kg, because of its lipid solubility.8

Protein binding

The plasma protein binding of dronabinol and its metabolites is approximately 97%.8

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.

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Route of elimination

Dronabinol and its biotransformation products are excreted in both feces and urine. Biliary excretion is the major route of excretion with about half of a radio-labeled oral dose being recovered from the feces within 72 hours as contrasted with 10 to 15% recovered from urine. Less than 5% of an oral dose is recovered unchanged in the feces.8

Due to its re-distribution, dronabinol and its metabolites may be excreted for prolonged periods of time. Following single-dose administration, dronabinol metabolites have been detected for more than 5 weeks in the urine and feces.8

In a study of dronabinol capsules involving AIDS patients, urinary cannabinoid/creatinine concentration ratios were studied bi-weekly over a six-week period. The urinary cannabinoid/creatinine ratio was closely correlated with the dose. No increase in the cannabinoid/creatinine ratio was observed after the first two weeks of treatment, indicating that steady-state cannabinoid levels had been reached. This conclusion is consistent with predictions based on the observed terminal half-life of dronabinol.8

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.8

Clearance

The value for clearance average is about 0.2 L/kg-hr but is highly variable due to the complexity of cannabinoid distribution.8

Adverse Effects
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Toxicity

SYNDROS, a synthetic cannabinoid containing alcohol, may cause fetal harm. Avoid the use of SYNDROS in pregnant women. Although there is little published data on the use of synthetic cannabinoids during pregnancy, the use of cannabis (e.g., marijuana) and the use of alcohol during pregnancy have been associated with adverse fetal/neonatal outcomes (see Clinical Considerations). Cannabinoids have been found in the umbilical cord blood of pregnant women who smoke cannabis. In animal reproduction studies, no teratogenicity was reported in mice administered dronabinol (delta-9-THC) at up to 30 times the MRHD (maximum recommended human doses) and up to 5 times the MRHD for patients with AIDS and cancer, respectively. Similar findings were reported in pregnant rats administered dronabinol at up to 5 to 20 times the MRHD and 3 times the MRHD for patients with AIDS and cancer, respectively. Decreased maternal weight gain and the number of viable pups and increased fetal mortality and early resorptions were observed in both species at doses that induced maternal toxicity. In rats, maternal administration of dronabinol from pregnancy (implantation) through weaning was associated with maternal toxicity, including mortality of pups, and adverse developmental and 10 neurodevelopmental effects on the pups at 2 to 20 times the MRHD for patients with AIDS and less than and up to 3.3 times the MRHD for patients with cancer.8

The estimated background risk of major birth defects and miscarriage for the indicated populations is unknown. All pregnancies have a background risk of birth defect, loss, or other adverse outcomes. In the U.S. general population, the estimated background risk of major birth defects and miscarriage in clinically recognized pregnancies is 2 to 4% and 15 to 20%, respectively.8

For mothers infected with the Human Immunodeficiency Virus (HIV), the Centers for Disease Control and Prevention recommend that HIV-infected mothers not breastfeed their infants to avoid risking postnatal transmission of HIV. Because of the potential for HIV transmission (in 12 HIV-negative infants) and serious adverse reactions in a breastfed infant, instruct mothers not to breastfeed if they are receiving SYNDROS. For mothers with nausea and vomiting associated with cancer chemotherapy, there are limited data on the presence of dronabinol in human milk, the effects on the breastfed infant, or the effects on milk production. The reported effects of inhaled cannabis transferred to the breastfeeding infant have been inconsistent and insufficient to establish causality. The developmental and health benefits of breastfeeding should be considered along with the mother’s clinical need for SYNDROS and any potential adverse effects on the breastfed infant from SYNDROS or from the underlying maternal condition.8

The safety and effectiveness of SYNDROS have not been established in pediatric patients. Pediatric patients may be more sensitive to the neurological and psychoactive effects of SYNDROS. SYNDROS contains the excipients 50% (w/w) dehydrated alcohol and 5.5% (w/w) propylene glycol. Ethanol competitively inhibits the metabolism of propylene glycol, which may lead to elevated concentrations of propylene glycol. Preterm neonates may be at increased risk of propylene glycol-associated adverse events due to diminished ability to metabolize propylene glycol, thereby, leading to accumulation.8

Clinical studies of dronabinol capsules in AIDS and cancer patients did not include sufficient numbers of subjects aged 65 and over to determine whether they respond differently from younger subjects. Elderly patients may be more sensitive to the neuropsychiatric and postural hypotensive effects of SYNDROS. Elderly patients with dementia are at increased risk for falls as a result of their underlying disease state, which may be exacerbated by the CNS effects of somnolence and dizziness associated with SYNDROS. These patients should be monitored closely and placed on fall precautions prior to initiating SYNDROS therapy. In antiemetic studies, no difference in efficacy was apparent in patients greater than 55 years of age compared to younger patients. In general, dose selection for an elderly patient should be cautious, usually starting at the low end of the dosing range, reflecting the greater frequency of falls decreased hepatic, renal, or cardiac function, increased sensitivity to psychoactive effects, and concomitant disease or other drugs therapy.8

SYNDROS contains dronabinol, the main psychoactive component in marijuana. Ingestion of high doses of dronabinol increases the risk of psychiatric adverse reactions if abused or misused, while continued administration can lead to addiction. Psychiatric adverse reactions may include psychosis, hallucinations, depersonalization, mood alteration, and paranoia. In vitro studies demonstrate that SYNDROS can be easily and effectively abused without manipulation. SYNDROS contains 50% (w/w) dehydrated alcohol. In a randomized, single-dose, double-blind, placebo- and active-controlled crossover pharmacodynamic study of 43 experienced marijuana smokers, “drug liking” responses and safety of SYNDROS were compared with placebo and dronabinol in sesame oil oral capsules. Treatment arms were 10 mg and 30 mg dronabinol capsules, 10 mg and 30 mg dronabinol from= SYNDROS, and placebo oral solution and capsules. Greater “drug liking” scores were reported with the 30 mg dose, compared with the 10 mg dose, for both SYNDROS and dronabinol-containing capsules. Overall, the pharmacodynamic results from this study demonstrated no statistically significant differences in various measures of drug liking for the doses taken, though the SYNDROS results were consistently greater than those of dronabinol capsules. Similarly, observed adverse reactions were greater for SYNDROS. The pharmacodynamic and safety effects of SYNDROS following multiple doses have not been evaluated. Patients should be instructed to keep SYNDROS in a secure place out of reach of others for whom the medication has not been prescribed.8

Physical dependence is a state that develops as a result of physiological adaptation in response to repeated drug use. Physical dependence manifests by drug class-specific withdrawal symptoms after abrupt discontinuation or a significant dose reduction of a drug. The appearance of a withdrawal syndrome when the administration of the drug is terminated is the only actual evidence of physical dependence. Physical dependence can develop during chronic therapy with SYNDROS and develops after chronic abuse of marijuana. A withdrawal syndrome was reported after the abrupt discontinuation of dronabinol capsules in subjects receiving dosages of 210 mg per day for 12 to 16 consecutive days. Within 12 hours after discontinuation, subjects manifested symptoms such as irritability, insomnia, and restlessness. By approximately 24 hours post-dronabinol discontinuation, withdrawal symptoms intensified to include “hot flashes”, sweating, rhinorrhea, loose stools, hiccoughs, and anorexia. These withdrawal symptoms gradually dissipated over the next 48 hours. Electroencephalographic changes consistent with the effects of drug withdrawal (hyperexcitation) were recorded in patients after abrupt dechallenge. Patients also complained of disturbed sleep for several weeks after discontinuing therapy with high dosages of dronabinol.8

Signs and symptoms of dronabinol overdose include drowsiness, euphoria, heightened sensory awareness, altered time perception, reddened conjunctiva, dry mouth, tachycardia, memory impairment, depersonalization, mood alteration, urinary retention, reduced bowel motility, decreased motor coordination, lethargy, slurred speech, and postural hypotension. Patients may also experience panic reactions if they have a prior history of nervousness or anxiety and seizures may occur in patients with existing seizure disorders. It is not known if dronabinol can be removed by dialysis in cases of overdose.8

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
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineDronabinol may increase the central nervous system depressant (CNS depressant) activities of 1,2-Benzodiazepine.
AbametapirThe serum concentration of Dronabinol can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Dronabinol can be increased when combined with Abatacept.
AbirateroneThe serum concentration of Dronabinol can be increased when it is combined with Abiraterone.
AbrocitinibThe metabolism of Abrocitinib can be decreased when combined with Dronabinol.
AcalabrutinibThe serum concentration of Dronabinol can be increased when it is combined with Acalabrutinib.
AcebutololThe metabolism of Acebutolol can be decreased when combined with Dronabinol.
AcenocoumarolThe metabolism of Acenocoumarol can be decreased when combined with Dronabinol.
AcetaminophenThe serum concentration of Dronabinol can be increased when it is combined with Acetaminophen.
AcetazolamideThe serum concentration of Dronabinol can be increased when it is combined with Acetazolamide.
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Food Interactions
  • Avoid alcohol. Patients with a history of substance abuse or dependence, including marijuana or alcohol, may be more likely to abuse SYNDROS as well.
  • Take before a meal. Because food delays the absorption of SYNDROS, administer the first dose on an empty stomach at least 30 minutes before eating.

Products

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Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
DronabinolCapsule5 mg/1OralActavis Pharma, Inc.2005-06-072019-05-31US flag
DronabinolCapsule2.5 mg/1OralAscend Laboratories, LLC2017-05-102021-09-30US flag
DronabinolCapsule2.5 mg/1OralMajor Pharmaceuticals2017-05-10Not applicableUS flag
DronabinolCapsule10 mg/1OralActavis Pharma, Inc.1994-08-112019-09-30US flag
DronabinolCapsule5 mg/1OralMajor Pharmaceuticals2021-03-03Not applicableUS flag
DronabinolCapsule10 mg/1OralAscend Laboratories, LLC2017-05-102021-09-30US flag
DronabinolCapsule2.5 mg/1Oralbryant ranch prepack2021-03-03Not applicableUS flag
DronabinolCapsule5 mg/1Oralbryant ranch prepack2021-03-03Not applicableUS flag
DronabinolCapsule2.5 mg/1OralActavis Pharma, Inc.1994-08-112019-05-31US flag
DronabinolCapsule5 mg/1OralAscend Laboratories, LLC2017-05-102021-04-30US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
DronabinolCapsule5 mg/1OralAkorn2014-06-20Not applicableUS flag
DronabinolCapsule, liquid filled5 mg/1OralMylan Pharmaceuticals2011-11-012016-06-30US flag
DronabinolCapsule5 mg/1OralAmerican Health Packaging2018-08-09Not applicableUS flag
DronabinolCapsule2.5 mg/1OralAvKARE2020-03-16Not applicableUS flag
DronabinolCapsule5 mg/1OralAscend Laboratories, LLC2021-03-03Not applicableUS flag
DronabinolCapsule5 mg/1OralPar Pharmaceutical, Inc.2008-06-27Not applicableUS flag
DronabinolCapsule2.5 mg/1OralAmerican Health Packaging2010-06-022020-01-31US flag
DronabinolCapsule2.5 mg/1OralCamber Pharmaceuticals Inc2020-02-10Not applicableUS flag
DronabinolCapsule2.5 mg/1OralRhodes Pharmaceuticals L.P.2018-06-26Not applicableUS flag
DronabinolCapsule5 mg/1OralMajor Pharmaceuticals2018-06-262023-01-31US flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
SativexDronabinol (2.7 mg / act) + Cannabidiol (2.5 mg / act)SprayBuccalGw Pharma Limited2005-06-22Not applicableCanada flag

Categories

ATC Codes
A04AD10 — Dronabinol
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / 2,2-dimethyl-1-benzopyran / Alkyl aryl ether / Aromatic heteropolycyclic compound / Benzenoid / Ether / Hydrocarbon derivative / Organic oxygen compound / Organooxygen compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
polyketide, diterpenoid, phytocannabinoid, benzochromene (CHEBI:66964) / Cannabinoids (C06972)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
7J8897W37S
CAS number
1972-08-3
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

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. [Article]
  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. [Article]
  3. Kaur R, Ambwani SR, Singh S: Endocannabinoid System: A Multi-Facet Therapeutic Target. Curr Clin Pharmacol. 2016;11(2):110-7. [Article]
  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. [Article]
  5. Alsherbiny MA, Li CG: Medicinal Cannabis-Potential Drug Interactions. Medicines (Basel). 2018 Dec 23;6(1). pii: medicines6010003. doi: 10.3390/medicines6010003. [Article]
  6. FDA Approved Drug Products: Syndros (Dronabinol) Oral Solution [Link]
  7. WHO Expert Committee on Drug Dependence Pre-Review: delta-9-tetrahydrocannibinol [Link]
  8. FDA Approved Drug Products: Syndros (Dronabinol) Oral Solution 2022 [Link]
  9. Health Canada Approved Drug Proucts: Marinol (Dronabinol) Oral Solution [Link]
Human Metabolome Database
HMDB0014613
KEGG Drug
D00306
KEGG Compound
C06972
PubChem Compound
16078
PubChem Substance
46508472
ChemSpider
15266
BindingDB
60994
RxNav
10402
ChEBI
66964
ChEMBL
CHEMBL465
ZINC
ZINC000001530625
Therapeutic Targets Database
DAP000207
PharmGKB
PA449421
Guide to Pharmacology
GtP Drug Page
PDBe Ligand
TCI
RxList
RxList Drug Page
Wikipedia
Dronabinol
PDB Entries
3ls4 / 6mp4 / 7m6m / 7m6o / 7m6q
FDA label
Download (414 KB)
MSDS
Download (51.4 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingOtherCannabis Use / Pregnancy Related1
4CompletedBasic ScienceHealthy Subjects (HS)1
4CompletedBasic SciencePost Traumatic Stress Disorder (PTSD)1
4CompletedTreatmentChest Pain1
4CompletedTreatmentMedical Abortion / Pain1
4CompletedTreatmentMultiple Sclerosis / Spasticity1
4Enrolling by InvitationTreatmentPostoperative pain1
4RecruitingTreatmentChronic Migraine / Medication Overuse Headache1
4RecruitingTreatmentOpioids Use / Total Knee Arthroplasty (TKA)1
4TerminatedSupportive CareHead And Neck Cancer / Lung Cancers / Oncologic Complications / Pancreatic Cancer / Poor Nutrition / Quality of Life (QOL)1

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
SolutionBuccal; Oral
SolutionBuccal; Oral25 mg
SprayBuccal
Spray, meteredTransmucosal
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)Region
US6703418No2004-03-092011-02-26US flag
US8222292No2012-07-172028-08-06US flag
US9345771No2016-05-242028-08-06US flag
US10265293No2019-04-232028-08-06US flag
US11253472No2008-08-062028-08-06US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)200 °C at 2.00E-02 mm HgNot Available
water solubility2.8 mg/L (at 23 °C)WHO Expert Committee on Drug Dependence Pre-Review: delta-9-tetrahydrocannibinol
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

Targets

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Details
1. Cannabinoid receptor 1
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Details
2. Cannabinoid receptor 2
Kind
Protein
Organism
Humans
Pharmacological action
Yes
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. [Article]
  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. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Inhibitor
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. [Article]
  2. Alsherbiny MA, Li CG: Medicinal Cannabis-Potential Drug Interactions. Medicines (Basel). 2018 Dec 23;6(1). pii: medicines6010003. doi: 10.3390/medicines6010003. [Article]
  3. Stout SM, Cimino NM: Exogenous cannabinoids as substrates, inhibitors, and inducers of human drug metabolizing enzymes: a systematic review. Drug Metab Rev. 2014 Feb;46(1):86-95. doi: 10.3109/03602532.2013.849268. Epub 2013 Oct 25. [Article]
  4. Kocis PT, Vrana KE: Delta-9-Tetrahydrocannabinol and Cannabidiol Drug-Drug Interactions. Med Cannabis Cannabinoids. 2020 Jul 7;3(1):61-73. doi: 10.1159/000507998. eCollection 2020 Aug. [Article]
  5. Qian Y, Gurley BJ, Markowitz JS: The Potential for Pharmacokinetic Interactions Between Cannabis Products and Conventional Medications. J Clin Psychopharmacol. 2019 Sep/Oct;39(5):462-471. doi: 10.1097/JCP.0000000000001089. [Article]
  6. FDA Approved Drug Products: Syndros (Dronabinol) Oral Solution [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Inhibitor
Inducer
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. [Article]
  2. Bland TM, Haining RL, Tracy TS, Callery PS: CYP2C-catalyzed delta9-tetrahydrocannabinol metabolism: kinetics, pharmacogenetics and interaction with phenytoin. Biochem Pharmacol. 2005 Oct 1;70(7):1096-103. doi: 10.1016/j.bcp.2005.07.007. [Article]
  3. Sachse-Seeboth C, Pfeil J, Sehrt D, Meineke I, Tzvetkov M, Bruns E, Poser W, Vormfelde SV, Brockmoller J: Interindividual variation in the pharmacokinetics of Delta9-tetrahydrocannabinol as related to genetic polymorphisms in CYP2C9. Clin Pharmacol Ther. 2009 Mar;85(3):273-6. doi: 10.1038/clpt.2008.213. Epub 2008 Nov 12. [Article]
  4. Nasrin S, Watson CJW, Perez-Paramo YX, Lazarus P: Cannabinoid Metabolites as Inhibitors of Major Hepatic CYP450 Enzymes, with Implications for Cannabis-Drug Interactions. Drug Metab Dispos. 2021 Dec;49(12):1070-1080. doi: 10.1124/dmd.121.000442. Epub 2021 Sep 7. [Article]
  5. Alsherbiny MA, Li CG: Medicinal Cannabis-Potential Drug Interactions. Medicines (Basel). 2018 Dec 23;6(1). pii: medicines6010003. doi: 10.3390/medicines6010003. [Article]
  6. Stout SM, Cimino NM: Exogenous cannabinoids as substrates, inhibitors, and inducers of human drug metabolizing enzymes: a systematic review. Drug Metab Rev. 2014 Feb;46(1):86-95. doi: 10.3109/03602532.2013.849268. Epub 2013 Oct 25. [Article]
  7. Kocis PT, Vrana KE: Delta-9-Tetrahydrocannabinol and Cannabidiol Drug-Drug Interactions. Med Cannabis Cannabinoids. 2020 Jul 7;3(1):61-73. doi: 10.1159/000507998. eCollection 2020 Aug. [Article]
  8. Qian Y, Gurley BJ, Markowitz JS: The Potential for Pharmacokinetic Interactions Between Cannabis Products and Conventional Medications. J Clin Psychopharmacol. 2019 Sep/Oct;39(5):462-471. doi: 10.1097/JCP.0000000000001089. [Article]
  9. FDA Approved Drug Products: Syndros (Dronabinol) Oral Solution [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Inhibitor
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. Nasrin S, Watson CJW, Perez-Paramo YX, Lazarus P: Cannabinoid Metabolites as Inhibitors of Major Hepatic CYP450 Enzymes, with Implications for Cannabis-Drug Interactions. Drug Metab Dispos. 2021 Dec;49(12):1070-1080. doi: 10.1124/dmd.121.000442. Epub 2021 Sep 7. [Article]
  2. Stout SM, Cimino NM: Exogenous cannabinoids as substrates, inhibitors, and inducers of human drug metabolizing enzymes: a systematic review. Drug Metab Rev. 2014 Feb;46(1):86-95. doi: 10.3109/03602532.2013.849268. Epub 2013 Oct 25. [Article]
  3. Qian Y, Gurley BJ, Markowitz JS: The Potential for Pharmacokinetic Interactions Between Cannabis Products and Conventional Medications. J Clin Psychopharmacol. 2019 Sep/Oct;39(5):462-471. doi: 10.1097/JCP.0000000000001089. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
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
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Stout SM, Cimino NM: Exogenous cannabinoids as substrates, inhibitors, and inducers of human drug metabolizing enzymes: a systematic review. Drug Metab Rev. 2014 Feb;46(1):86-95. doi: 10.3109/03602532.2013.849268. Epub 2013 Oct 25. [Article]
  2. Nasrin S, Watson CJW, Perez-Paramo YX, Lazarus P: Cannabinoid Metabolites as Inhibitors of Major Hepatic CYP450 Enzymes, with Implications for Cannabis-Drug Interactions. Drug Metab Dispos. 2021 Dec;49(12):1070-1080. doi: 10.1124/dmd.121.000442. Epub 2021 Sep 7. [Article]
  3. Qian Y, Gurley BJ, Markowitz JS: The Potential for Pharmacokinetic Interactions Between Cannabis Products and Conventional Medications. J Clin Psychopharmacol. 2019 Sep/Oct;39(5):462-471. doi: 10.1097/JCP.0000000000001089. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
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
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. Nasrin S, Watson CJW, Perez-Paramo YX, Lazarus P: Cannabinoid Metabolites as Inhibitors of Major Hepatic CYP450 Enzymes, with Implications for Cannabis-Drug Interactions. Drug Metab Dispos. 2021 Dec;49(12):1070-1080. doi: 10.1124/dmd.121.000442. Epub 2021 Sep 7. [Article]
  2. Alsherbiny MA, Li CG: Medicinal Cannabis-Potential Drug Interactions. Medicines (Basel). 2018 Dec 23;6(1). pii: medicines6010003. doi: 10.3390/medicines6010003. [Article]
  3. Stout SM, Cimino NM: Exogenous cannabinoids as substrates, inhibitors, and inducers of human drug metabolizing enzymes: a systematic review. Drug Metab Rev. 2014 Feb;46(1):86-95. doi: 10.3109/03602532.2013.849268. Epub 2013 Oct 25. [Article]
  4. Qian Y, Gurley BJ, Markowitz JS: The Potential for Pharmacokinetic Interactions Between Cannabis Products and Conventional Medications. J Clin Psychopharmacol. 2019 Sep/Oct;39(5):462-471. doi: 10.1097/JCP.0000000000001089. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Nasrin S, Watson CJW, Perez-Paramo YX, Lazarus P: Cannabinoid Metabolites as Inhibitors of Major Hepatic CYP450 Enzymes, with Implications for Cannabis-Drug Interactions. Drug Metab Dispos. 2021 Dec;49(12):1070-1080. doi: 10.1124/dmd.121.000442. Epub 2021 Sep 7. [Article]
  2. Alsherbiny MA, Li CG: Medicinal Cannabis-Potential Drug Interactions. Medicines (Basel). 2018 Dec 23;6(1). pii: medicines6010003. doi: 10.3390/medicines6010003. [Article]
  3. Stout SM, Cimino NM: Exogenous cannabinoids as substrates, inhibitors, and inducers of human drug metabolizing enzymes: a systematic review. Drug Metab Rev. 2014 Feb;46(1):86-95. doi: 10.3109/03602532.2013.849268. Epub 2013 Oct 25. [Article]
  4. Qian Y, Gurley BJ, Markowitz JS: The Potential for Pharmacokinetic Interactions Between Cannabis Products and Conventional Medications. J Clin Psychopharmacol. 2019 Sep/Oct;39(5):462-471. doi: 10.1097/JCP.0000000000001089. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Triglyceride lipase activity
Specific Function
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acy...
Gene Name
CES1
Uniprot ID
P23141
Uniprot Name
Liver carboxylesterase 1
Molecular Weight
62520.62 Da
References
  1. Qian Y, Gurley BJ, Markowitz JS: The Potential for Pharmacokinetic Interactions Between Cannabis Products and Conventional Medications. J Clin Psychopharmacol. 2019 Sep/Oct;39(5):462-471. doi: 10.1097/JCP.0000000000001089. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
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. Ruhaak LR, Felth J, Karlsson PC, Rafter JJ, Verpoorte R, Bohlin L: Evaluation of the cyclooxygenase inhibiting effects of six major cannabinoids isolated from Cannabis sativa. Biol Pharm Bull. 2011;34(5):774-8. doi: 10.1248/bpb.34.774. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
Inducer
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. Alsherbiny MA, Li CG: Medicinal Cannabis-Potential Drug Interactions. Medicines (Basel). 2018 Dec 23;6(1). pii: medicines6010003. doi: 10.3390/medicines6010003. [Article]
  2. Stout SM, Cimino NM: Exogenous cannabinoids as substrates, inhibitors, and inducers of human drug metabolizing enzymes: a systematic review. Drug Metab Rev. 2014 Feb;46(1):86-95. doi: 10.3109/03602532.2013.849268. Epub 2013 Oct 25. [Article]
  3. Qian Y, Gurley BJ, Markowitz JS: The Potential for Pharmacokinetic Interactions Between Cannabis Products and Conventional Medications. J Clin Psychopharmacol. 2019 Sep/Oct;39(5):462-471. doi: 10.1097/JCP.0000000000001089. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
This enzyme metabolizes arachidonic acid predominantly via a NADPH-dependent olefin epoxidation to all four regioisomeric cis-epoxyeicosatrienoic acids. One of the predominant enzymes responsible f...
Gene Name
CYP2J2
Uniprot ID
P51589
Uniprot Name
Cytochrome P450 2J2
Molecular Weight
57610.165 Da
References
  1. Kocis PT, Vrana KE: Delta-9-Tetrahydrocannabinol and Cannabidiol Drug-Drug Interactions. Med Cannabis Cannabinoids. 2020 Jul 7;3(1):61-73. doi: 10.1159/000507998. eCollection 2020 Aug. [Article]
  2. Qian Y, Gurley BJ, Markowitz JS: The Potential for Pharmacokinetic Interactions Between Cannabis Products and Conventional Medications. J Clin Psychopharmacol. 2019 Sep/Oct;39(5):462-471. doi: 10.1097/JCP.0000000000001089. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Oxygen binding
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
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Stout SM, Cimino NM: Exogenous cannabinoids as substrates, inhibitors, and inducers of human drug metabolizing enzymes: a systematic review. Drug Metab Rev. 2014 Feb;46(1):86-95. doi: 10.3109/03602532.2013.849268. Epub 2013 Oct 25. [Article]
  2. Qian Y, Gurley BJ, Markowitz JS: The Potential for Pharmacokinetic Interactions Between Cannabis Products and Conventional Medications. J Clin Psychopharmacol. 2019 Sep/Oct;39(5):462-471. doi: 10.1097/JCP.0000000000001089. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Oxygen binding
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
CYP3A7
Uniprot ID
P24462
Uniprot Name
Cytochrome P450 3A7
Molecular Weight
57525.03 Da
References
  1. Stout SM, Cimino NM: Exogenous cannabinoids as substrates, inhibitors, and inducers of human drug metabolizing enzymes: a systematic review. Drug Metab Rev. 2014 Feb;46(1):86-95. doi: 10.3109/03602532.2013.849268. Epub 2013 Oct 25. [Article]
  2. Qian Y, Gurley BJ, Markowitz JS: The Potential for Pharmacokinetic Interactions Between Cannabis Products and Conventional Medications. J Clin Psychopharmacol. 2019 Sep/Oct;39(5):462-471. doi: 10.1097/JCP.0000000000001089. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Oxygen binding
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
CYP1B1
Uniprot ID
Q16678
Uniprot Name
Cytochrome P450 1B1
Molecular Weight
60845.33 Da
References
  1. Stout SM, Cimino NM: Exogenous cannabinoids as substrates, inhibitors, and inducers of human drug metabolizing enzymes: a systematic review. Drug Metab Rev. 2014 Feb;46(1):86-95. doi: 10.3109/03602532.2013.849268. Epub 2013 Oct 25. [Article]
  2. Qian Y, Gurley BJ, Markowitz JS: The Potential for Pharmacokinetic Interactions Between Cannabis Products and Conventional Medications. J Clin Psychopharmacol. 2019 Sep/Oct;39(5):462-471. doi: 10.1097/JCP.0000000000001089. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
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. Alsherbiny MA, Li CG: Medicinal Cannabis-Potential Drug Interactions. Medicines (Basel). 2018 Dec 23;6(1). pii: medicines6010003. doi: 10.3390/medicines6010003. [Article]
  2. Stout SM, Cimino NM: Exogenous cannabinoids as substrates, inhibitors, and inducers of human drug metabolizing enzymes: a systematic review. Drug Metab Rev. 2014 Feb;46(1):86-95. doi: 10.3109/03602532.2013.849268. Epub 2013 Oct 25. [Article]
  3. Qian Y, Gurley BJ, Markowitz JS: The Potential for Pharmacokinetic Interactions Between Cannabis Products and Conventional Medications. J Clin Psychopharmacol. 2019 Sep/Oct;39(5):462-471. doi: 10.1097/JCP.0000000000001089. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Steroid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
Gene Name
UGT1A1
Uniprot ID
P22309
Uniprot Name
UDP-glucuronosyltransferase 1-1
Molecular Weight
59590.91 Da
References
  1. Nasrin S, Watson CJW, Perez-Paramo YX, Lazarus P: Cannabinoid Metabolites as Inhibitors of Major Hepatic CYP450 Enzymes, with Implications for Cannabis-Drug Interactions. Drug Metab Dispos. 2021 Dec;49(12):1070-1080. doi: 10.1124/dmd.121.000442. Epub 2021 Sep 7. [Article]
  2. Mazur A, Lichti CF, Prather PL, Zielinska AK, Bratton SM, Gallus-Zawada A, Finel M, Miller GP, Radominska-Pandya A, Moran JH: Characterization of human hepatic and extrahepatic UDP-glucuronosyltransferase enzymes involved in the metabolism of classic cannabinoids. Drug Metab Dispos. 2009 Jul;37(7):1496-504. doi: 10.1124/dmd.109.026898. Epub 2009 Apr 1. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Retinoic acid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Isoform 2 lacks transferase activity but acts as a negative reg...
Gene Name
UGT1A3
Uniprot ID
P35503
Uniprot Name
UDP-glucuronosyltransferase 1-3
Molecular Weight
60337.835 Da
References
  1. Mazur A, Lichti CF, Prather PL, Zielinska AK, Bratton SM, Gallus-Zawada A, Finel M, Miller GP, Radominska-Pandya A, Moran JH: Characterization of human hepatic and extrahepatic UDP-glucuronosyltransferase enzymes involved in the metabolism of classic cannabinoids. Drug Metab Dispos. 2009 Jul;37(7):1496-504. doi: 10.1124/dmd.109.026898. Epub 2009 Apr 1. [Article]
  2. Nasrin S, Watson CJW, Perez-Paramo YX, Lazarus P: Cannabinoid Metabolites as Inhibitors of Major Hepatic CYP450 Enzymes, with Implications for Cannabis-Drug Interactions. Drug Metab Dispos. 2021 Dec;49(12):1070-1080. doi: 10.1124/dmd.121.000442. Epub 2021 Sep 7. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Retinoic acid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols. Isoform 2 lacks trans...
Gene Name
UGT1A9
Uniprot ID
O60656
Uniprot Name
UDP-glucuronosyltransferase 1-9
Molecular Weight
59940.495 Da
References
  1. Nasrin S, Watson CJW, Perez-Paramo YX, Lazarus P: Cannabinoid Metabolites as Inhibitors of Major Hepatic CYP450 Enzymes, with Implications for Cannabis-Drug Interactions. Drug Metab Dispos. 2021 Dec;49(12):1070-1080. doi: 10.1124/dmd.121.000442. Epub 2021 Sep 7. [Article]
  2. Mazur A, Lichti CF, Prather PL, Zielinska AK, Bratton SM, Gallus-Zawada A, Finel M, Miller GP, Radominska-Pandya A, Moran JH: Characterization of human hepatic and extrahepatic UDP-glucuronosyltransferase enzymes involved in the metabolism of classic cannabinoids. Drug Metab Dispos. 2009 Jul;37(7):1496-504. doi: 10.1124/dmd.109.026898. Epub 2009 Apr 1. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Protein kinase c binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Isoform 2 lacks transferase activity but acts as a negative reg...
Gene Name
UGT1A10
Uniprot ID
Q9HAW8
Uniprot Name
UDP-glucuronosyltransferase 1-10
Molecular Weight
59809.075 Da
References
  1. Mazur A, Lichti CF, Prather PL, Zielinska AK, Bratton SM, Gallus-Zawada A, Finel M, Miller GP, Radominska-Pandya A, Moran JH: Characterization of human hepatic and extrahepatic UDP-glucuronosyltransferase enzymes involved in the metabolism of classic cannabinoids. Drug Metab Dispos. 2009 Jul;37(7):1496-504. doi: 10.1124/dmd.109.026898. Epub 2009 Apr 1. [Article]
  2. Nasrin S, Watson CJW, Perez-Paramo YX, Lazarus P: Cannabinoid Metabolites as Inhibitors of Major Hepatic CYP450 Enzymes, with Implications for Cannabis-Drug Interactions. Drug Metab Dispos. 2021 Dec;49(12):1070-1080. doi: 10.1124/dmd.121.000442. Epub 2021 Sep 7. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
No
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. [Article]
  2. Stout SM, Cimino NM: Exogenous cannabinoids as substrates, inhibitors, and inducers of human drug metabolizing enzymes: a systematic review. Drug Metab Rev. 2014 Feb;46(1):86-95. doi: 10.3109/03602532.2013.849268. Epub 2013 Oct 25. [Article]
  3. Qian Y, Gurley BJ, Markowitz JS: The Potential for Pharmacokinetic Interactions Between Cannabis Products and Conventional Medications. J Clin Psychopharmacol. 2019 Sep/Oct;39(5):462-471. doi: 10.1097/JCP.0000000000001089. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Curator comments
Cannabinoids can cause dysregulation of P-glycoprotein but at higher concentrations than are normally present in cannabis smokers.
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. [Article]
  2. Alsherbiny MA, Li CG: Medicinal Cannabis-Potential Drug Interactions. Medicines (Basel). 2018 Dec 23;6(1). pii: medicines6010003. doi: 10.3390/medicines6010003. [Article]
  3. Stout SM, Cimino NM: Exogenous cannabinoids as substrates, inhibitors, and inducers of human drug metabolizing enzymes: a systematic review. Drug Metab Rev. 2014 Feb;46(1):86-95. doi: 10.3109/03602532.2013.849268. Epub 2013 Oct 25. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Transporter activity
Specific Function
Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotre...
Gene Name
ABCC1
Uniprot ID
P33527
Uniprot Name
Multidrug resistance-associated protein 1
Molecular Weight
171589.5 Da
References
  1. Stout SM, Cimino NM: Exogenous cannabinoids as substrates, inhibitors, and inducers of human drug metabolizing enzymes: a systematic review. Drug Metab Rev. 2014 Feb;46(1):86-95. doi: 10.3109/03602532.2013.849268. Epub 2013 Oct 25. [Article]
  2. Qian Y, Gurley BJ, Markowitz JS: The Potential for Pharmacokinetic Interactions Between Cannabis Products and Conventional Medications. J Clin Psychopharmacol. 2019 Sep/Oct;39(5):462-471. doi: 10.1097/JCP.0000000000001089. [Article]

Drug created at June 13, 2005 13:24 / Updated at January 27, 2023 00:46