Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C21H30O2 |
Molecular Weight | 314.4617 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCC1=CC(O)=C2[C@@H]3C=C(C)CC[C@H]3C(C)(C)OC2=C1
InChI
InChIKey=CYQFCXCEBYINGO-IAGOWNOFSA-N
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
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.
CNS Activity
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 |
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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 |
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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 |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/11245634/ Page: 5.0 |
likely | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/11245634/ |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 13.0 |
yes | |||
Page: 13.0 |
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 |
---|---|---|
Examination of the immunosuppressive effect of delta9-tetrahydrocannabinol in streptozotocin-induced autoimmune diabetes. | 2001 Apr |
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An ab initio theoretical study of the stereoisomers of tetrahydrocannabinols. | 2001 Apr |
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Tetrahydrocannabinol-induced apoptosis of cultured cortical neurones is associated with cytochrome c release and caspase-3 activation. | 2001 Apr |
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Cannabinoid inhibition of capsaicin-sensitive sensory neurotransmission in the rat mesenteric arterial bed. | 2001 Apr 20 |
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Receptor-independent effects of natural cannabinoids in rat peritoneal mast cells in vitro. | 2001 Apr 23 |
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(R)-methanandamide and Delta 9-THC as discriminative stimuli in rats: tests with the cannabinoid antagonist SR-141716 and the endogenous ligand anandamide. | 2001 Aug |
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Marijuana smoke and Delta(9)-tetrahydrocannabinol promote necrotic cell death but inhibit Fas-mediated apoptosis. | 2001 Aug 1 |
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CB1 cannabinoid receptor-mediated neurite remodeling in mouse neuroblastoma N1E-115 cells. | 2001 Aug 15 |
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Screening method for 11-nor-delta9-tetrahydrocannabinol-9-carboxylic acid in urine using hollow fiber membrane solvent microextraction with in-tube derivatization. | 2001 Aug 25 |
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Endogenous cannabinoid, 2-arachidonoylglycerol, attenuates naloxone-precipitated withdrawal signs in morphine-dependent mice. | 2001 Aug 3 |
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Activation of the CB1 cannabinoid receptor protects cultured mouse spinal neurons against excitotoxicity. | 2001 Aug 31 |
|
Cannabinoid receptors are absent in insects. | 2001 Aug 6 |
|
Influence of treatment of Tourette syndrome with delta9-tetrahydrocannabinol (delta9-THC) on neuropsychological performance. | 2001 Jan |
|
Behavioral suppression induced by cannabinoids is due to activation of the arachidonic acid cascade in rats. | 2001 Jan 19 |
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High rates of midazolam self-administration in squirrel monkeys. | 2001 Jul |
|
Chronic treatment with Delta(9)-tetrahydrocannabinol enhances the locomotor response to amphetamine and heroin. Implications for vulnerability to drug addiction. | 2001 Jul |
|
The pharmacological activity of inhalation exposure to marijuana smoke in mice. | 2001 Jul 1 |
|
SPME-GC analysis of THC in saliva samples collected with "EPITOPE" device. | 2001 Jul 15 |
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Hemodynamic effects of cannabinoids: coronary and cerebral vasodilation mediated by cannabinoid CB(1) receptors. | 2001 Jul 6 |
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Cannabinoids for control of chemotherapy induced nausea and vomiting: quantitative systematic review. | 2001 Jul 7 |
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Involvement of somatodendritic 5-HT(1A) receptors in Delta(9)-tetrahydrocannabinol-induced hypothermia in the rat. | 2001 Jul-Aug |
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Interaction between delta-9-tetrahydrocannabinol and indomethacin. | 2001 Jul-Aug |
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Concordance between verbal report and urine screen of recent marijuana use in adolescents. | 2001 Jul-Aug |
|
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 Jun |
|
Effects of fluvoxamine on ethanol-reinforced behavior in the rat. | 2001 Jun |
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Cannabinoid inhibition of the capsaicin-induced calcium response in rat dorsal root ganglion neurones. | 2001 Mar |
|
Agonist efficacy and receptor efficiency in heterozygous CB1 knockout mice: relationship of reduced CB1 receptor density to G-protein activation. | 2001 May |
|
The role of central and peripheral Cannabinoid1 receptors in the antihyperalgesic activity of cannabinoids in a model of neuropathic pain. | 2001 May |
|
Critical role of the endogenous cannabinoid system in mouse pup suckling and growth. | 2001 May 11 |
|
Delta9-tetrahydrocannabinol enhances cortical and hippocampal acetylcholine release in vivo: a microdialysis study. | 2001 May 11 |
|
Interactions between A-9THC and capsaicin on isolated lamb bladder detrusor. | 2001 May-Jul |
|
[Passive exposure in detection of low blood and urine cannabinoid concentrations]. | 2001 May-Jun |
|
Cannabinoid-induced motor incoordination through the cerebellar CB(1) receptor in mice. | 2001 May-Jun |
|
Delta-9-tetrahydrocannabinol differentially suppresses cisplatin-induced emesis and indices of motor function via cannabinoid CB(1) receptors in the least shrew. | 2001 May-Jun |
|
Precipitated cannabinoid withdrawal is reversed by Delta(9)-tetrahydrocannabinol or clonidine. | 2001 May-Jun |
|
Delta9-tetrahydrocannabivarin as a marker for the ingestion of marijuana versus Marinol: results of a clinical study. | 2001 Oct |
|
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 Oct |
|
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 Oct |
|
Solid-phase extraction and GC-MS analysis of THC-COOH method optimized for a high-throughput forensic drug-testing laboratory. | 2001 Oct |
|
A cannabinoid mechanism in relapse to cocaine seeking. | 2001 Oct |
|
Ethanol increases plasma Delta(9)-tetrahydrocannabinol (THC) levels and subjective effects after marihuana smoking in human volunteers. | 2001 Oct 1 |
|
Differential effects of delta 9-THC on spatial reference and working memory in mice. | 2001 Sep |
|
Identification and quantitation of 11-nor-delta9-tetrahydrocannabivarin-9-carboxylic acid, a major metabolite of delta9-tetrahydrocannabivarin. | 2001 Sep |
|
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 Sep |
|
Effects of chronic Delta(9)-tetrahydrocannabinol treatment on hippocampal extracellular acetylcholine concentration and alternation performance in the T-maze. | 2001 Sep |
|
Opioid and cannabinoid modulation of precipitated withdrawal in delta(9)-tetrahydrocannabinol and morphine-dependent mice. | 2001 Sep |
|
Neuroprotection by Delta9-tetrahydrocannabinol, the main active compound in marijuana, against ouabain-induced in vivo excitotoxicity. | 2001 Sep 1 |
|
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 Sep 15 |
|
R(+)-methanandamide induces cyclooxygenase-2 expression in human neuroglioma cells via a non-cannabinoid receptor-mediated mechanism. | 2001 Sep 7 |
|
Hu 210: a potent tool for investigations of the cannabinoid system. | 2001 Summer |
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
by
admin
on
Edited
Mon Mar 31 17:35:29 GMT 2025
by
admin
on
Mon Mar 31 17:35:29 GMT 2025
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Record UNII |
7J8897W37S
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000008010
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FDA ORPHAN DRUG |
668918
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DEA NO. |
7369
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NCI_THESAURUS |
C267
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LIVERTOX |
NBK548830
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WHO-ATC |
A04AD10
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FDA ORPHAN DRUG |
498215
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CFR |
21 CFR 1308.35
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FDA ORPHAN DRUG |
652218
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FDA ORPHAN DRUG |
54890
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EU-Orphan Drug |
EU/3/16/1621
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WHO-ATC |
N02BG10
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NDF-RT |
N0000175782
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FDA ORPHAN DRUG |
628818
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WHO-VATC |
QA04AD10
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FDA ORPHAN DRUG |
620417
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FDA ORPHAN DRUG |
549616
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FDA ORPHAN DRUG |
734820
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Code System | Code | Type | Description | ||
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CHEMBL465
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10402
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4109
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134454
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2424
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5547
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SUB06407MIG
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DB00470
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T-59
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DTXSID6021327
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m10624
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PRIMARY | Merck Index | ||
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TETRAHYDROCANNABINOL
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66964
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Dronabinol
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7J8897W37S
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7J8897W37S
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D013759
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C867
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16078
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1972-08-3
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100000090615
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6471
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Related Record | Type | Details | ||
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METABOLIC ENZYME -> SUBSTRATE |
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METABOLIC ENZYME -> SUBSTRATE |
MINOR
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SALT/SOLVATE -> PARENT |
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TARGET -> AGONIST |
Mouse AtT-20 neuroblastoma cells stably transfected with human CB1
EC50
|
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METABOLIC ENZYME -> SUBSTRATE |
MINOR
|
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METABOLIC ENZYME -> SUBSTRATE |
MAJOR
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METABOLIC ENZYME -> INHIBITOR |
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METABOLIC ENZYME -> SUBSTRATE |
|
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PARENT -> ACTIVE CONSTITUENT ALWAYS PRESENT |
Delta-9-tetrahydrocannabinol class | Euphoriant | Analgesic | Anti-inflammatory | Antioxidant | Antiemetic
|
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TARGET -> AGONIST |
Mouse AtT-20 neuroblastoma cells stably transfected with human CB2
EC50
|
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METABOLIC ENZYME -> SUBSTRATE |
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Related Record | Type | Details | ||
---|---|---|---|---|
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PRODRUG -> METABOLITE ACTIVE |
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PRODRUG -> METABOLITE ACTIVE |
|
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PRODRUG -> METABOLITE ACTIVE |
|
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PRODRUG -> METABOLITE ACTIVE |
|
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METABOLITE ACTIVE -> PARENT |
Equpotent to DELTA.9-TETRAHYDROCANNABINOL on CB1 receptors
|
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PRODRUG -> METABOLITE ACTIVE |
|
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METABOLITE INACTIVE -> PARENT |
URINE
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METABOLITE -> PARENT |
IN VITRO
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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Related Record | Type | Details | ||
---|---|---|---|---|
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ACTIVE MOIETY |
|