Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | 2C21H30O2.C4H6O4 |
| Molecular Weight | 747.0114 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)CCC(O)=O.CCCCCC1=CC(O)=C2[C@@H]3C=C(C)CC[C@H]3C(C)(C)OC2=C1.CCCCCC4=CC(O)=C5[C@@H]6C=C(C)CC[C@H]6C(C)(C)OC5=C4
InChI
InChIKey=ZTNSQRHQTPQSCH-VKLRDTKISA-N
InChI=1S/2C21H30O2.C4H6O4/c2*1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15;5-3(6)1-2-4(7)8/h2*11-13,16-17,22H,5-10H2,1-4H3;1-2H2,(H,5,6)(H,7,8)/t2*16-,17-;/m11./s1
| Molecular Formula | C4H6O4 |
| Molecular Weight | 118.088 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C21H30O2 |
| Molecular Weight | 314.4617 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: description was created based on several sources, including http://www.who.int/medicines/areas/quality_safety/4.2DronabinolCritReview.pdf
Curator's Comment: description was created based on several sources, including http://www.who.int/medicines/areas/quality_safety/4.2DronabinolCritReview.pdf
Dronabinol also known as (−)-trans-delta9-tetrahydrocannabinol is an active ingredient of cannabis. The drug was approved by FDA for the treatment of anorexia in patients with AIDS and chemotherapy-induced nausea and vomiting. Dronabinol exerts its action by activating CB1 and CB2 recepors which makes it a CNS active medicine.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P34972 Gene ID: 1269.0 Gene Symbol: CNR2 Target Organism: Homo sapiens (Human) |
3.13 nM [Ki] | ||
Target ID: P21554|||Q5UB37 Gene ID: 1268.0 Gene Symbol: CNR1 Target Organism: Homo sapiens (Human) |
5.05 nM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | MARINOL Approved UseMARINOL Capsules 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. Launch Date1985 |
|||
| Secondary | MARINOL Approved UseMARINOL Capsules 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. Launch Date1985 |
|||
| Secondary | MARINOL Approved UseMARINOL Capsules 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. Launch Date1985 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.32 ng/mL |
2.5 mg 2 times / day multiple, oral dose: 2.5 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
DRONABINOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
2.96 ng/mL |
5 mg 2 times / day multiple, oral dose: 5 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
DRONABINOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
7.88 ng/mL |
10 mg 2 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
DRONABINOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2.88 ng × h/mL |
2.5 mg 2 times / day multiple, oral dose: 2.5 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
DRONABINOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
6.16 ng × h/mL |
5 mg 2 times / day multiple, oral dose: 5 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
DRONABINOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
15.2 ng × h/mL |
10 mg 2 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
DRONABINOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
3% |
2.5 mg 2 times / day multiple, oral dose: 2.5 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
DRONABINOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
3% |
5 mg 2 times / day multiple, oral dose: 5 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
DRONABINOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
3% |
10 mg 2 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
DRONABINOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Page: 5.0 |
likely | |||
| yes |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| yes | ||||
| yes | yes (pharmacogenomic study) Comment: Published data indicate a 2- to 3-fold higher dronabinol exposure in individuals carrying genetic variants associated with diminished CYP2C9 function Page: 13.0 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Ethanol increases plasma Delta(9)-tetrahydrocannabinol (THC) levels and subjective effects after marihuana smoking in human volunteers. | 2001-10-01 |
|
| Delta9-tetrahydrocannabivarin as a marker for the ingestion of marijuana versus Marinol: results of a clinical study. | 2001-10 |
|
| A comparison of Roche Kinetic Interaction of Microparticles in Solution (KIMS) assay for cannabinoids and GC-MS analysis for 11-nor-9-carboxy-delta9-tetrahydrocannabinol. | 2001-10 |
|
| The determination of 11-nor-delta9-tetrahydrocannabinol-9-carboxylic acid (THC-COOH) in hair using negative ion gas chromatography-mass spectrometry and high-volume injection. | 2001-10 |
|
| Solid-phase extraction and GC-MS analysis of THC-COOH method optimized for a high-throughput forensic drug-testing laboratory. | 2001-10 |
|
| Temporal indication of marijuana use can be estimated from plasma and urine concentrations of delta9-tetrahydrocannabinol, 11-hydroxy-delta9-tetrahydrocannabinol, and 11-nor-delta9-tetrahydrocannabinol-9-carboxylic acid. | 2001-10 |
|
| Simultaneous determination of delta9-tetrahydrocannabinol and 11-nor-9-carboxy-delta9-tetrahydrocannabinol in human plasma by solid-phase extraction and gas chromatography-negative ion chemical ionization-mass spectrometry. | 2001-10 |
|
| A cannabinoid mechanism in relapse to cocaine seeking. | 2001-10 |
|
| Cannabinoid activity curtails cocaine craving. | 2001-10 |
|
| Electrophysiological evidence of serotonergic impairment in long-term MDMA ("ecstasy") users. | 2001-10 |
|
| Marijuana abstinence effects in marijuana smokers maintained in their home environment. | 2001-10 |
|
| Neuropsychological performance in long-term cannabis users. | 2001-10 |
|
| [Antiarrhythmic properties of a cannabinoid (CB) receptor agonist]. | 2001-09-18 |
|
| Antitumor effects of ajulemic acid (CT3), a synthetic non-psychoactive cannabinoid. | 2001-09-15 |
|
| Fast confirmation of 11-nor-9-carboxy-Delta(9)-tetrahydrocannabinol (THC-COOH) in urine by LC/MS/MS using negative atmospheric-pressure chemical ionisation (APCI). | 2001-09-15 |
|
| R(+)-methanandamide induces cyclooxygenase-2 expression in human neuroglioma cells via a non-cannabinoid receptor-mediated mechanism. | 2001-09-07 |
|
| Neuroprotection by Delta9-tetrahydrocannabinol, the main active compound in marijuana, against ouabain-induced in vivo excitotoxicity. | 2001-09-01 |
|
| Differential effects of delta 9-THC on spatial reference and working memory in mice. | 2001-09 |
|
| The psychoactive ingredient of marijuana induces behavioural sensitization. | 2001-09 |
|
| Identification and quantitation of 11-nor-delta9-tetrahydrocannabivarin-9-carboxylic acid, a major metabolite of delta9-tetrahydrocannabivarin. | 2001-09 |
|
| Role of gonadal steroids in the corticotropin-releasing hormone and proopiomelanocortin gene expression response to Delta(9)-tetrahydrocannabinol in the hypothalamus of the rat. | 2001-09 |
|
| Effects of chronic Delta(9)-tetrahydrocannabinol treatment on hippocampal extracellular acetylcholine concentration and alternation performance in the T-maze. | 2001-09 |
|
| Opioid and cannabinoid modulation of precipitated withdrawal in delta(9)-tetrahydrocannabinol and morphine-dependent mice. | 2001-09 |
|
| Activation of the CB1 cannabinoid receptor protects cultured mouse spinal neurons against excitotoxicity. | 2001-08-31 |
|
| Screening method for 11-nor-delta9-tetrahydrocannabinol-9-carboxylic acid in urine using hollow fiber membrane solvent microextraction with in-tube derivatization. | 2001-08-25 |
|
| Involvement of somatodendritic 5-HT(1A) receptors in Delta(9)-tetrahydrocannabinol-induced hypothermia in the rat. | 2001-08-18 |
|
| [Passive exposure in detection of low blood and urine cannabinoid concentrations]. | 2001-08-18 |
|
| CB1 cannabinoid receptor-mediated neurite remodeling in mouse neuroblastoma N1E-115 cells. | 2001-08-15 |
|
| Cannabinoid receptors are absent in insects. | 2001-08-06 |
|
| Interactions between A-9THC and capsaicin on isolated lamb bladder detrusor. | 2001-08-03 |
|
| Endogenous cannabinoid, 2-arachidonoylglycerol, attenuates naloxone-precipitated withdrawal signs in morphine-dependent mice. | 2001-08-03 |
|
| Marijuana smoke and Delta(9)-tetrahydrocannabinol promote necrotic cell death but inhibit Fas-mediated apoptosis. | 2001-08-01 |
|
| (R)-methanandamide and Delta 9-THC as discriminative stimuli in rats: tests with the cannabinoid antagonist SR-141716 and the endogenous ligand anandamide. | 2001-08 |
|
| Interaction between delta-9-tetrahydrocannabinol and indomethacin. | 2001-07-21 |
|
| Concordance between verbal report and urine screen of recent marijuana use in adolescents. | 2001-07-18 |
|
| SPME-GC analysis of THC in saliva samples collected with "EPITOPE" device. | 2001-07-15 |
|
| Cannabinoids for control of chemotherapy induced nausea and vomiting: quantitative systematic review. | 2001-07-07 |
|
| Hemodynamic effects of cannabinoids: coronary and cerebral vasodilation mediated by cannabinoid CB(1) receptors. | 2001-07-06 |
|
| The pharmacological activity of inhalation exposure to marijuana smoke in mice. | 2001-07-01 |
|
| Delta 9-tetrahydrocannabinol-induced MAPK/ERK and Elk-1 activation in vivo depends on dopaminergic transmission. | 2001-07 |
|
| High rates of midazolam self-administration in squirrel monkeys. | 2001-07 |
|
| Chronic treatment with Delta(9)-tetrahydrocannabinol enhances the locomotor response to amphetamine and heroin. Implications for vulnerability to drug addiction. | 2001-07 |
|
| Cannabinoid-induced motor incoordination through the cerebellar CB(1) receptor in mice. | 2001-06-23 |
|
| Delta-9-tetrahydrocannabinol differentially suppresses cisplatin-induced emesis and indices of motor function via cannabinoid CB(1) receptors in the least shrew. | 2001-06-23 |
|
| Precipitated cannabinoid withdrawal is reversed by Delta(9)-tetrahydrocannabinol or clonidine. | 2001-06-23 |
|
| Activation of type II cannabinoid receptors improves myocardial tolerance to arrhythmogenic effects of coronary occlusion and reperfusion. | 2001-06 |
|
| Cannabinoid receptor agonist and antagonist effects on motor function in normal and 1-methyl-4-phenyl-1,2,5,6-tetrahydropyridine (MPTP)-treated non-human primates. | 2001-06 |
|
| Critical role of the endogenous cannabinoid system in mouse pup suckling and growth. | 2001-05-11 |
|
| Delta9-tetrahydrocannabinol enhances cortical and hippocampal acetylcholine release in vivo: a microdialysis study. | 2001-05-11 |
|
| Hu 210: a potent tool for investigations of the cannabinoid system. | 2001 |
Sample Use Guides
Appetite Stimulation: Initially, 2.5 mg capsules should be administered orally twice daily, before lunch and supper. For patients unable to tolerate this 5 mg/day dosage, the dosage can be reduced to 2.5 mg/day, administered as a single dose in the evening or at bedtime. Antiemetic: it is best administered at an initial dose of 5 mg/m2, given 1 to 3 hours prior to the administration of chemotherapy, then every 2 to 4 hours after chemotherapy is given, for a total of 4 to 6 doses/day. Should the 5 mg/m2 dose prove to be ineffective, and in the absence of significant side effects, the dose may be escalated by 2.5 mg/m2 increments to a maximum of 15 mg/m2 per dose.
Route of Administration:
Oral
| Substance Class |
Chemical
Created
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Edited
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| Record UNII |
M67MK6J9X0
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| Record Status |
Validated (UNII)
|
| Record Version |
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Preferred Name | English |
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Created by
admin on Mon Mar 31 18:26:27 GMT 2025 , Edited by admin on Mon Mar 31 18:26:27 GMT 2025
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M67MK6J9X0
Created by
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