DRONABINOL

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

Structure Search

SMILES

[H][C@@]12CCC(C)=C[C@@]1([H])C3=C(O)C=C(CCCCC)C=C3OC2(C)C

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

HIDE SMILES / InChI

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2006/018651s025s026lbl.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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cannabinoid receptor 2 27 Target ID: P34972 Gene ID: 1269.0 Gene Symbol: CNR2 Target Organism: Homo sapiens (Human) Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2006/018651s025s026lbl.pdf	Agonist 2678		3.13 nM [Ki]
Cannabinoid receptor 1 30 Target ID: P21554\|\|\|Q5UB37 Gene ID: 1268.0 Gene Symbol: CNR1 Target Organism: Homo sapiens (Human) Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2006/018651s025s026lbl.pdf	Agonist 2678		5.05 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Anorexia in AIDS 2 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2006/018651s025s026lbl.pdf	Primary	Approved 8429	MARINOL Approved Use MARINOL 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 Date 1985
Vomiting in cancer chemotherapy 2 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2006/018651s025s026lbl.pdf	Secondary	Approved 8429	MARINOL Approved Use MARINOL 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 Date 1985
Nausea in cancer chemotherapy 2 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2006/018651s025s026lbl.pdf	Secondary	Approved 8429	MARINOL Approved Use MARINOL 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 Date 1985

C_max

Value	Dose	Analyte	Population
7.88 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/018651s029lbl.pdf	10 mg 2 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered:	DRONABINOL unknown	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
1.32 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/018651s029lbl.pdf	2.5 mg 2 times / day multiple, oral dose: 2.5 mg route of administration: Oral experiment type: MULTIPLE co-administered:	DRONABINOL unknown	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
2.96 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/018651s029lbl.pdf	5 mg 2 times / day multiple, oral dose: 5 mg route of administration: Oral experiment type: MULTIPLE co-administered:	DRONABINOL unknown	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

AUC

Value	Dose	Analyte	Population
15.2 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/018651s029lbl.pdf	10 mg 2 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered:	DRONABINOL unknown	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
2.88 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/018651s029lbl.pdf	2.5 mg 2 times / day multiple, oral dose: 2.5 mg route of administration: Oral experiment type: MULTIPLE co-administered:	DRONABINOL unknown	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
6.16 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/018651s029lbl.pdf	5 mg 2 times / day multiple, oral dose: 5 mg route of administration: Oral experiment type: MULTIPLE co-administered:	DRONABINOL unknown	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

F_unbound

Value	Dose	Analyte	Population
3% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/018651s029lbl.pdf	10 mg 2 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered:	DRONABINOL unknown	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
3% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/018651s029lbl.pdf	2.5 mg 2 times / day multiple, oral dose: 2.5 mg route of administration: Oral experiment type: MULTIPLE co-administered:	DRONABINOL unknown	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
3% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/018651s029lbl.pdf	5 mg 2 times / day multiple, oral dose: 5 mg route of administration: Oral experiment type: MULTIPLE co-administered:	DRONABINOL unknown	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

Doses

Dose	Population	Adverse events
30 mg 1 times / day single, oral Highest studied dose Dose: 30 mg, 1 times / day Route: oral Route: single Dose: 30 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/205525Orig1s000MedR.pdf Page: nda/2016/205525Orig1s000MedR.pdf - p.40	unhealthy, mean age 36 years n = 40 Health Status: unhealthy Condition: cannabinoid abuse Age Group: mean age 36 years Sex: M+F Population Size: 40 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/205525Orig1s000MedR.pdf Page: nda/2016/205525Orig1s000MedR.pdf - p.40	Other AEs: Palpitations, Tachycardia... Other AEs: Palpitations (2.5%) Tachycardia (2.5%) Photophobia (2.5%) Vision blurred (2.5%) Eye irritation (2.5%) Dry mouth (40%) Fatigue (30%) Feeling of relaxation (5%) Hunger (10%) Feeling hot (5%) Thirst (5%) Chills (2.5%) Upper respiratory tract infection (2.5%) Hordeolum (2.5%) Increased appetite (7.5%) Polydipsia (2.5%) Sensation of heaviness (2.5%) Muscle spasms (2.5%) Somnolence (37.5%) Headache (10%) Dizziness (5%) Paraesthesia (2.5%) Dysgeusia (5%) Hypoaesthesia (2.5%) Hypotonia (2.5%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/205525Orig1s000MedR.pdf Page: nda/2016/205525Orig1s000MedR.pdf - p.40
2.5 mg 2 times / day multiple, oral Dose: 2.5 mg, 2 times / day Route: oral Route: multiple Dose: 2.5 mg, 2 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT01253408	unhealthy n = 10 Health Status: unhealthy Condition: Irritable Bowel Syndrome Population Size: 10 Sources: https://clinicaltrials.gov/ct2/show/NCT01253408	Other AEs: Headache... Other AEs: Headache (below serious, 3 patients) Sources: https://clinicaltrials.gov/ct2/show/NCT01253408
20 mg 2 times / day multiple, oral Dose: 20 mg, 2 times / day Route: oral Route: multiple Dose: 20 mg, 2 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT00217971	unhealthy n = 79 Health Status: unhealthy Condition: Marijuana Addiction Population Size: 79 Sources: https://clinicaltrials.gov/ct2/show/NCT00217971	Other AEs: Diabetes, Concussion... Other AEs: Diabetes (serious, 1 patient) Concussion (serious, 1 patient) Nausea (below serious, 5 patients) Sources: https://clinicaltrials.gov/ct2/show/NCT00217971

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737	substrate 1037

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A1 110		CYP1A1 108

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP1A1 218	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/11245634/ Page: 5.0	likely
CYP1A1 218	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/11245634/	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 1737	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/018651s029lbl.pdf#page=13 Page: 13.0	yes
CYP2C9 1037	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/018651s029lbl.pdf#page=13 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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/018651s029lbl.pdf#page=13 Page: 13.0

Sourcing

Vendor/Aggregator	ID	URL
Alfa Chemistry	26514	https://www.alfa-chemistry.com/delta9-tetrahydrocannabinol-cas-1972-08-3-item-290835.htm
Aurora Fine Chemicals LLC	A17.878.362	http://online.aurorafinechemicals.com/info?ID=A17.878.362
Avantor Inc	76124-756	https://us.vwr.com/store/product/24885630/clinical-forensic-and-toxicology-standards-delta-9-tetrahydrocannabinol-thc-crm-restek
BOC Sciences	26514	https://www.bocsci.com/product/delta-9-tetrahydrocannabinol-cas-1972-08-3-334884.html
BenchChem	B526632	https://www.benchchem.com/product/b526632
ChemFaces	CFN91898	http://www.chemfaces.com/natural/Delta-9-Tetrahydrocannabinol-CFN91898.html
ChemMol	97900439	http://www.chemmol.com/chemmol/97900439.html
LGC Standards	DRE-A17405100ME-100	https://www.lgcstandards.com/US/en/p/DRE-A17405100ME-100
LGC Standards	DRE-A17405100ME-1000	https://www.lgcstandards.com/US/en/p/DRE-A17405100ME-1000
LGC Standards	LGCAMP1088.00-01	https://www.lgcstandards.com/US/en/p/LGCAMP1088.00-01
LGC Standards	LGCAMP1088.00-02	https://www.lgcstandards.com/US/en/p/LGCAMP1088.00-02
LGC Standards	LGCAMP1088.00-05	https://www.lgcstandards.com/US/en/p/LGCAMP1088.00-05
Sigma-Aldrich	T-005_CERILLIAN	https://www.sigmaaldrich.com/catalog/product/cerillian/t005?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	56296_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/56296?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	94785_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/94785?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	T2386_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/t2386?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	1651621_USP	https://www.sigmaaldrich.com/catalog/product/usp/1651621?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S526632	http://www.smolecule.com/products/s526632
THE BioTek	bt-266534	https://www.thebiotek.com/product/inhibitors/bt-266534

PubMed

Title	Date	PubMed
Examination of the immunosuppressive effect of delta9-tetrahydrocannabinol in streptozotocin-induced autoimmune diabetes.	2001 Apr	11357882
(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	11498713
Marijuana smoke and Delta(9)-tetrahydrocannabinol promote necrotic cell death but inhibit Fas-mediated apoptosis.	2001 Aug 1	11485387
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	11522063
Activation of the CB1 cannabinoid receptor protects cultured mouse spinal neurons against excitotoxicity.	2001 Aug 31	11514075
Cannabinoid receptors are absent in insects.	2001 Aug 6	11447587
Delta 9-tetrahydrocannabinol-induced MAPK/ERK and Elk-1 activation in vivo depends on dopaminergic transmission.	2001 Jul	11553284
High rates of midazolam self-administration in squirrel monkeys.	2001 Jul	11548111
Chronic treatment with Delta(9)-tetrahydrocannabinol enhances the locomotor response to amphetamine and heroin. Implications for vulnerability to drug addiction.	2001 Jul	11445192
The pharmacological activity of inhalation exposure to marijuana smoke in mice.	2001 Jul 1	11376914
SPME-GC analysis of THC in saliva samples collected with "EPITOPE" device.	2001 Jul 15	11390146
Hemodynamic effects of cannabinoids: coronary and cerebral vasodilation mediated by cannabinoid CB(1) receptors.	2001 Jul 6	11448486
Cannabinoids for control of chemotherapy induced nausea and vomiting: quantitative systematic review.	2001 Jul 7	11440936
Interaction between delta-9-tetrahydrocannabinol and indomethacin.	2001 Jul-Aug	11464074
Concordance between verbal report and urine screen of recent marijuana use in adolescents.	2001 Jul-Aug	11456081
Activation of type II cannabinoid receptors improves myocardial tolerance to arrhythmogenic effects of coronary occlusion and reperfusion.	2001 Jun	11586395
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	11465637
Effects of fluvoxamine on ethanol-reinforced behavior in the rat.	2001 Jun	11356922
Cannabinoid-induced alterations in brain disposition of drugs of abuse.	2001 Jun 1	11331071
Delta(9)-THC stimulates food intake in Lewis rats: effects on chow, high-fat and sweet high-fat diets.	2001 Mar	11325410
Agonist efficacy and receptor efficiency in heterozygous CB1 knockout mice: relationship of reduced CB1 receptor density to G-protein activation.	2001 May	11359870
Critical role of the endogenous cannabinoid system in mouse pup suckling and growth.	2001 May 11	11426843
Delta9-tetrahydrocannabinol enhances cortical and hippocampal acetylcholine release in vivo: a microdialysis study.	2001 May 11	11426837
Interactions between A-9THC and capsaicin on isolated lamb bladder detrusor.	2001 May-Jul	11482756
[Antiarrhythmic properties of a cannabinoid (CB) receptor agonist].	2001 May-Jun	11558437
[Passive exposure in detection of low blood and urine cannabinoid concentrations].	2001 May-Jun	11508050
Cannabinoid-induced motor incoordination through the cerebellar CB(1) receptor in mice.	2001 May-Jun	11420093
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	11420092
Precipitated cannabinoid withdrawal is reversed by Delta(9)-tetrahydrocannabinol or clonidine.	2001 May-Jun	11420084
Delta9-tetrahydrocannabivarin as a marker for the ingestion of marijuana versus Marinol: results of a clinical study.	2001 Oct	11599601
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	11599600
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	11599599
Solid-phase extraction and GC-MS analysis of THC-COOH method optimized for a high-throughput forensic drug-testing laboratory.	2001 Oct	11599598
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 Oct	11599597
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 Oct	11599596
A cannabinoid mechanism in relapse to cocaine seeking.	2001 Oct	11590440
Cannabinoid activity curtails cocaine craving.	2001 Oct	11590424
Electrophysiological evidence of serotonergic impairment in long-term MDMA ("ecstasy") users.	2001 Oct	11579003
Marijuana abstinence effects in marijuana smokers maintained in their home environment.	2001 Oct	11576029
Neuropsychological performance in long-term cannabis users.	2001 Oct	11576028
Ethanol increases plasma Delta(9)-tetrahydrocannabinol (THC) levels and subjective effects after marihuana smoking in human volunteers.	2001 Oct 1	11543984
Differential effects of delta 9-THC on spatial reference and working memory in mice.	2001 Sep	11594438
The psychoactive ingredient of marijuana induces behavioural sensitization.	2001 Sep	11576193
Identification and quantitation of 11-nor-delta9-tetrahydrocannabivarin-9-carboxylic acid, a major metabolite of delta9-tetrahydrocannabivarin.	2001 Sep	11550824
Effects of chronic Delta(9)-tetrahydrocannabinol treatment on hippocampal extracellular acetylcholine concentration and alternation performance in the T-maze.	2001 Sep	11522331
Opioid and cannabinoid modulation of precipitated withdrawal in delta(9)-tetrahydrocannabinol and morphine-dependent mice.	2001 Sep	11504797
Neuroprotection by Delta9-tetrahydrocannabinol, the main active compound in marijuana, against ouabain-induced in vivo excitotoxicity.	2001 Sep 1	11517236
Antitumor effects of ajulemic acid (CT3), a synthetic non-psychoactive cannabinoid.	2001 Sep 15	11551521
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	11516894
Hu 210: a potent tool for investigations of the cannabinoid system.	2001 Summer	11474421

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

Unknown

Name

Type

Language

DRONABINOL

Official Name

English

.DELTA.1-THC

Common Name

English

MARINOL

Brand Name

English

QCD 84924

Code

English

ABBOTT 40566

Code

English

THC

Common Name

English

SP 104

Code

English

TETRAHYDROCANNABINOLS (-)-TRANS-.DELTA.9-FORM

Common Name

English

TETRAHYDROCANNABINOL

Common Name

English

(6AR,10AR)-6,6,9-TRIMETHYL-3-PENTYL-6A,7,8,10A-TETRAHYDRO-6H-DIBENZO(B,D)PYRAN-1-OL

Common Name

English

DELTA-9-TETRAHYDROCANNABINOL

Common Name

English

DELTA-9-THC

Common Name

English

(6aR,10aR)-6a,7,8,10a-Tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-ol

Common Name

English

ABBOTT-40566

Code

English

DRONABINOL [ORANGE BOOK]

Common Name

English

J882F

Code

English

Dronabinol [WHO-DD]

Common Name

English

.DELTA.9-THC

Common Name

English

QCD-84924

Code

English

AD313 component dronabinol

Common Name

English

DRONABINOL [VANDF]

Common Name

English

dronabinol [INN]

Common Name

English

TETRAHYDROCANNABINOL, DELTA-9 TRANS

Common Name

English

SP-104

Code

English

.DELTA.-9-TETRAHYDROCANNABINOL

Common Name

English

6H-DIBENZO(B,D)PYRAN-1-OL, 6A,7,8,10A-TETRAHYDRO-6,6,9-TRIMETHYL-3-PENTYL-, (6AR,10AR)-

Common Name

English

SCI-110 component dronabinol

Code

English

DELTA-9-TETRAHYDROCANNABINOL (CANNABIS SATIVA EXTRACT)

Common Name

English

.DELTA.9-TETRAHYDROCANNABINOL

Common Name

English

DRONABINOL [USAN]

Common Name

English

(-)-.DELTA.1-3,4-TRANS-TETRAHYDROCANNABINOL

Common Name

English

AD-313 component dronabinol

Common Name

English

DRONABINOL [HSDB]

Common Name

English

DRONABINOL [MART.]

Common Name

English

DRONABINOL [USP MONOGRAPH]

Common Name

English

NSC-134454

Code

English

TETRAHYDROCANNABINOLS (-)-TRANS-.DELTA.9-FORM [MI]

Common Name

English

6H-DIBENZO(B,D)PYRAN-1-OL, 6A,7,8,10A-TETRAHYDRO-6,6,9-TRIMETHYL-3-PENTYL-, (6AR-TRANS)-

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000008010