Dronabinol

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

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Dronabinol (DB00470)

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Weight

Average: 314.4617
Monoisotopic: 314.224580204

Chemical Formula

C₂₁H₃₀O₂

Synonyms

• .DELTA.1-THC
• (-)-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

• Anorexia
• Chemotherapy-Induced Nausea and Vomiting

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.

Target	Actions	Organism
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 C_max and AUC_inf 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 (C_max and AUC_inf) 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.

Hover over products below to view reaction partners

• Dronabinol
  • 11-Hydroxy-delta-9-THC
    • 11-Hydroxy-delta-9-THC-glucuronide
    • 11-Nor-9-carboxy-delta-9-THC
      • 11-nor-9-carboxy-delta-9-THC-glucuronide
    • 8,11-Dihydroxy-delta-9-THC
  • 7-beta-Hydroxy-delta-9-THC
  • 7-alpha-Hydroxy-delta-9-THC
  • 8-Hydroxy-delta-9-THC
    • 8,11-Dihydroxy-delta-9-THC
  • 8-beta-Hydroxy-delta-9-THC
  • 9-alpha,10-alpha-epoxyhexahydrocannabinol
  • 11-OH-delata-Tetrahydrocannabinol
  • 7-OH-delta-9-Tetrahydrocannabinol
  • 7alpha-OH-delta-9-Tetrahydrocannabinol
  • 8-OH-delta-9-Tetrahydrocannabinol
  • 8alpha-OH-delta-9-Tetrahydrocannabinol

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/Enzyme	Allele name	Genotype(s)	Defining Change(s)	Type(s)	Description	Details
Cytochrome P450 2C9	CYP2C9*2	Not Available	430C>T	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2C9	CYP2C9*3	Not Available	1075A>C	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2C9	CYP2C9*4	Not Available	1076T>C	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2C9	CYP2C9*5	Not Available	1080C>G	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2C9	CYP2C9*8	Not Available	449G>A	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2C9	CYP2C9*11	Not Available	1003C>T	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2C9	CYP2C9*12	Not Available	1465C>T	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2C9	CYP2C9*13	Not Available	269T>C	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2C9	CYP2C9*14	Not Available	374G>A	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2C9	CYP2C9*16	Not Available	895A>G	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2C9	CYP2C9*18	Not Available	1075A>C / 1190A>C  … show all	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2C9	CYP2C9*26	Not Available	389C>G	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2C9	CYP2C9*28	Not Available	641A>T	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2C9	CYP2C9*30	Not Available	1429G>A	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2C9	CYP2C9*33	Not Available	395G>A	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2C9	CYP2C9*6	Not Available	818delA	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2C9	CYP2C9*15	Not Available	485C>A	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2C9	CYP2C9*25	Not Available	353_362delAGAAATGGAA	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2C9	CYP2C9*35	Not Available	374G>T / 430C>T	Effect Inferred	Poor 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.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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1,2-Benzodiazepine	Dronabinol may increase the central nervous system depressant (CNS depressant) activities of 1,2-Benzodiazepine.
Abametapir	The serum concentration of Dronabinol can be increased when it is combined with Abametapir.
Abatacept	The metabolism of Dronabinol can be increased when combined with Abatacept.
Abrocitinib	The metabolism of Abrocitinib can be decreased when combined with Dronabinol.
Acalabrutinib	The serum concentration of Dronabinol can be increased when it is combined with Acalabrutinib.
Acebutolol	The metabolism of Acebutolol can be decreased when combined with Dronabinol.
Acenocoumarol	The metabolism of Acenocoumarol can be decreased when combined with Dronabinol.
Acetaminophen	The serum concentration of Dronabinol can be increased when it is combined with Acetaminophen.
Acetazolamide	The serum concentration of Dronabinol can be increased when it is combined with Acetazolamide.
Acetohexamide	The metabolism of Acetohexamide can be decreased when combined with Dronabinol.

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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

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Dronabinol	Capsule	5 mg/1	Oral	Ascend Laboratories, LLC	2017-05-10	2021-04-30
Dronabinol	Capsule	2.5 mg/1	Oral	Major Pharmaceuticals	2017-05-10	Not applicable
Dronabinol	Capsule	5 mg/1	Oral	Actavis Pharma, Inc.	2005-06-07	2019-05-31
Dronabinol	Capsule	2.5 mg/1	Oral	Ascend Laboratories, LLC	2017-05-10	2021-09-30
Dronabinol	Capsule	2.5 mg/1	Oral	bryant ranch prepack	2021-03-03	Not applicable
Dronabinol	Capsule	5 mg/1	Oral	Major Pharmaceuticals	2021-03-03	Not applicable
Dronabinol	Capsule	5 mg/1	Oral	bryant ranch prepack	2021-03-03	Not applicable
Dronabinol	Capsule	10 mg/1	Oral	Actavis Pharma, Inc.	1994-08-11	2019-09-30
Dronabinol	Capsule	10 mg/1	Oral	Ascend Laboratories, LLC	2017-05-10	2021-09-30
Dronabinol	Capsule	2.5 mg/1	Oral	Major Pharmaceuticals	2021-03-03	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Dronabinol	Capsule	10 mg/1	Oral	Lannett Company, Inc.	2018-05-18	Not applicable
Dronabinol	Capsule	2.5 mg/1	Oral	AvKARE	2020-03-16	Not applicable
Dronabinol	Capsule, liquid filled	10 mg/1	Oral	Mylan Pharmaceuticals	2011-11-01	2016-05-31
Dronabinol	Capsule	5 mg/1	Oral	Rhodes Pharmaceuticals L.P.	2018-06-26	Not applicable
Dronabinol	Capsule	10 mg/1	Oral	Ascend Laboratories, LLC	2021-03-03	Not applicable
Dronabinol	Capsule	5 mg/1	Oral	American Health Packaging	2018-08-09	Not applicable
Dronabinol	Capsule	2.5 mg/1	Oral	Camber Pharmaceuticals Inc	2020-02-10	Not applicable
Dronabinol	Capsule	5 mg/1	Oral	Physicians Total Care, Inc.	2008-08-19	Not applicable
Dronabinol	Capsule	5 mg/1	Oral	Akorn	2014-06-20	Not applicable
Dronabinol	Capsule	10 mg/1	Oral	AvKARE	2020-03-16	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Sativex	Dronabinol (2.7 mg / act) + Cannabidiol (2.5 mg / act)	Spray	Buccal	Gw Pharma Limited	2005-06-22	Not applicable

Categories

ATC Codes

A04AD10 — Dronabinol

• A04AD — Other antiemetics
• A04A — ANTIEMETICS AND ANTINAUSEANTS
• A04 — ANTIEMETICS AND ANTINAUSEANTS
• A — ALIMENTARY TRACT AND METABOLISM

Drug Categories

• Agents producing tachycardia
• Alimentary Tract and Metabolism
• Analgesics
• Analgesics, Non-Narcotic
• Antiemetics and Antinauseants
• BCRP/ABCG2 Inhibitors
• Cannabinoid Receptor Agonists
• Cannabinoids and similars
• Central Nervous System Agents
• Central Nervous System Depressants
• Cytochrome P-450 CYP1A2 Inhibitors
• Cytochrome P-450 CYP1A2 Inhibitors (strength unknown)
• Cytochrome P-450 CYP2A6 Inhibitors
• Cytochrome P-450 CYP2A6 Inhibitors (strength unknown)
• Cytochrome P-450 CYP2B6 Inhibitors
• Cytochrome P-450 CYP2B6 Inhibitors (strength unknown)
• Cytochrome P-450 CYP2C19 Inhibitors
• Cytochrome P-450 CYP2C19 inhibitors (strength unknown)
• Cytochrome P-450 CYP2C19 Substrates
• Cytochrome P-450 CYP2C9 Inducers
• Cytochrome P-450 CYP2C9 Inducers (strength unknown)
• Cytochrome P-450 CYP2C9 Inhibitors
• Cytochrome P-450 CYP2C9 Inhibitors (strength unknown)
• Cytochrome P-450 CYP2C9 Substrates
• Cytochrome P-450 CYP2D6 Inhibitors
• Cytochrome P-450 CYP2D6 Inhibitors (strength unknown)
• Cytochrome P-450 CYP3A Inhibitors
• Cytochrome P-450 CYP3A Substrates
• Cytochrome P-450 CYP3A4 Inhibitors
• Cytochrome P-450 CYP3A4 Inhibitors (strength unknown)
• Cytochrome P-450 CYP3A4 Substrates
• Cytochrome P-450 CYP3A5 Inhibitors
• Cytochrome P-450 CYP3A5 Inhibitors (weak)
• Cytochrome P-450 CYP3A7 Inhibitors
• Cytochrome P-450 CYP3A7 Inhibitors (weak)
• Cytochrome P-450 Enzyme Inducers
• Cytochrome P-450 Enzyme Inhibitors
• Cytochrome P-450 Substrates
• Hallucinogens
• Hormones, Hormone Substitutes, and Hormone Antagonists
• Miscellaneous Antiemetics
• Neurotransmitter Agents
• P-glycoprotein inhibitors
• Peripheral Nervous System Agents
• Psychotropic Drugs
• Sensory System Agents
• Terpenes
• UGT1A1 Substrates
• UGT1A3 substrates
• UGT1A9 Substrates

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]

External Links

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 / 7p4j

FDA label

Download (414 KB)

MSDS

Download (51.4 KB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
4	Active Not Recruiting	Other	Cannabis Use / Pregnancy Related	1
4	Completed	Basic Science	Healthy Subjects (HS)	1
4	Completed	Basic Science	Post Traumatic Stress Disorder (PTSD)	1
4	Completed	Treatment	Chest Pain	1
4	Completed	Treatment	Medical Abortion / Pain	1
4	Completed	Treatment	Multiple Sclerosis / Spasticity	1
4	Enrolling by Invitation	Treatment	Postoperative pain	1
4	Not Yet Recruiting	Treatment	Trauma Injury	1
4	Recruiting	Treatment	Chronic Migraine / Medication Overuse Headache	1
4	Recruiting	Treatment	Opioids Use / Total Knee Arthroplasty (TKA)	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

Form	Route	Strength
Capsule	Oral	10 mg/1
Capsule	Oral	5 mg/1
Capsule, liquid filled	Oral	10 mg/1
Capsule, liquid filled	Oral	2.5 mg/1
Capsule, liquid filled	Oral	5 mg/1
Capsule	Oral	2.5 mg/1
Capsule	Oral	2.5 mg
Capsule	Oral	5 mg
Capsule	Oral	10 mg
Solution	Buccal; Oral
Solution	Buccal; Oral	25 mg
Spray	Buccal
Spray, metered	Transmucosal
Solution	Oral	5 mg/1mL

Prices

Unit description	Cost	Unit
Marinol 10 mg capsule	29.86USD	capsule
Dronabinol 10 mg capsule	19.26USD	capsule
Marinol 5 mg capsule	16.0USD	capsule
Dronabinol 5 mg capsule	11.8USD	capsule
Marinol 2.5 mg capsule	8.02USD	capsule
Dronabinol 2.5 mg capsule	5.11USD	capsule

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
US6703418	No	2004-03-09	2011-02-26
US8222292	No	2012-07-17	2028-08-06
US9345771	No	2016-05-24	2028-08-06
US10265293	No	2019-04-23	2028-08-06
US11253472	No	2008-08-06	2028-08-06

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	200 °C at 2.00E-02 mm Hg	Not Available
water solubility	2.8 mg/L (at 23 °C)	WHO Expert Committee on Drug Dependence Pre-Review: delta-9-tetrahydrocannibinol
logP	5.648	Not Available
pKa	10.6	PHYSICIAN'S DESK REFERENCE (1998)

Predicted Properties

Property	Value	Source
Water Solubility	0.00263 mg/mL	ALOGPS
logP	7.29	ALOGPS
logP	5.94	Chemaxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	9.34	Chemaxon
pKa (Strongest Basic)	-4.9	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	2	Chemaxon
Hydrogen Donor Count	1	Chemaxon
Polar Surface Area	29.46 Å2	Chemaxon
Rotatable Bond Count	4	Chemaxon
Refractivity	96.73 m3·mol-1	Chemaxon
Polarizability	38.96 Å3	Chemaxon
Number of Rings	3	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	No	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	Yes	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.9949
Blood Brain Barrier	+	0.9685
Caco-2 permeable	+	0.7607
P-glycoprotein substrate	Substrate	0.8458
P-glycoprotein inhibitor I	Non-inhibitor	0.5548
P-glycoprotein inhibitor II	Inhibitor	0.7191
Renal organic cation transporter	Non-inhibitor	0.8169
CYP450 2C9 substrate	Non-substrate	0.7522
CYP450 2D6 substrate	Non-substrate	0.9116
CYP450 3A4 substrate	Substrate	0.7199
CYP450 1A2 substrate	Inhibitor	0.6567
CYP450 2C9 inhibitor	Inhibitor	0.5352
CYP450 2D6 inhibitor	Non-inhibitor	0.7307
CYP450 2C19 inhibitor	Inhibitor	0.7683
CYP450 3A4 inhibitor	Non-inhibitor	0.6771
CYP450 inhibitory promiscuity	High CYP Inhibitory Promiscuity	0.8349
Ames test	Non AMES toxic	0.9132
Carcinogenicity	Non-carcinogens	0.8947
Biodegradation	Not ready biodegradable	0.9725
Rat acute toxicity	2.5940 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.7714
hERG inhibition (predictor II)	Non-inhibitor	0.8136

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Mass Spectrum (Electron Ionization)	MS	splash10-01pp-4792000000-06532e533cb7794b7c37
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available

Targets

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Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	17	N/A	N/A	A28293
IC 50 (nM)	2.8	N/A	N/A	A28292
Ki (nM)	10	N/A	N/A	A28293
Ki (nM)	17	N/A	N/A	A28289
Ki (nM)	2.9	N/A	N/A	A28290
Ki (nM)	28.5	N/A	N/A	A28288
Ki (nM)	40	N/A	N/A	A28291
Ki (nM)	41	N/A	N/A	A28285 / A28286 / A28287 / A28294

Details

Binding Properties1. 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]

Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	1.5	N/A	N/A	A28290
IC 50 (nM)	9.5	N/A	N/A	A28292
Ki (nM)	24	N/A	N/A	A28293
Ki (nM)	25	N/A	N/A	A28288
Ki (nM)	3.3	N/A	N/A	A28289
Ki (nM)	36	N/A	N/A	A28285 / A28287 / A28295 / A28296 / A28291 / A28297 / A28298 / A28294
Ki (nM)	41	N/A	N/A	A28290

Details

Binding Properties2. 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]

×

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Drug created at June 13, 2005 13:24 / Updated at September 30, 2023 15:27