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

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

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 2637		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 2637		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 8307	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 4.86345605E11
Vomiting in cancer chemotherapy 2 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2006/018651s025s026lbl.pdf	Secondary	Approved 8307	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 4.86345605E11
Nausea in cancer chemotherapy 2 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2006/018651s025s026lbl.pdf	Secondary	Approved 8307	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 4.86345605E11

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 1670	substrate 985

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A1 104		CYP1A1 103

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP1A1 206	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/11245634/ Page: 5.0	likely
CYP1A1 206	inducer 1515 Sources: https://pubmed.ncbi.nlm.nih.gov/11245634/	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 1670	substrate 3264 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/018651s029lbl.pdf#page=13 Page: 13.0	yes
CYP2C9 985	substrate 3264 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
Time-dependent differences of repeated administration with Delta9-tetrahydrocannabinol in proenkephalin and cannabinoid receptor gene expression and G-protein activation by mu-opioid and CB1-cannabinoid receptors in the caudate-putamen.	1999 Apr 6	10101241
Acute injection of drugs with low addictive potential (delta(9)-tetrahydrocannabinol, 3,4-methylenedioxymethamphetamine, lysergic acid diamide) causes a much higher c-fos expression in limbic brain areas than highly addicting drugs (cocaine and morphine).	1999 Aug 25	10521585
Repeated administration of delta9-tetrahydrocannabinol produces a differential time related responsiveness on proenkephalin, proopiomelanocortin and corticotropin releasing factor gene expression in the hypothalamus and pituitary gland of the rat.	1999 Mar	10219981
Increased mortality, hypoactivity, and hypoalgesia in cannabinoid CB1 receptor knockout mice.	1999 May 11	10318961
Sex steroid influence on cannabinoid CB(1) receptor mRNA and endocannabinoid levels in the anterior pituitary gland.	2000 Apr 2	10733937
Levels, metabolism, and pharmacological activity of anandamide in CB(1) cannabinoid receptor knockout mice: evidence for non-CB(1), non-CB(2) receptor-mediated actions of anandamide in mouse brain.	2000 Dec	11080195
Cannabinoid CB(1) receptors colocalize with tyrosine hydroxylase in cultured fetal mesencephalic neurons and their activation increases the levels of this enzyme.	2000 Feb 28	10700552
Anti-tumoral action of cannabinoids: involvement of sustained ceramide accumulation and extracellular signal-regulated kinase activation.	2000 Mar	10700234
Prenatal Delta(9)-tetrahydrocannabinol exposure modifies proenkephalin gene expression in the fetal rat brain: sex-dependent differences.	2000 Mar 15	10727732
Studies on [3H]CP-55940 binding in the human central nervous system: regional specific changes in density of cannabinoid-1 receptors associated with schizophrenia and cannabis use.	2001	11311783
An ab initio theoretical study of the stereoisomers of tetrahydrocannabinols.	2001 Apr	11349815
Receptor-independent effects of natural cannabinoids in rat peritoneal mast cells in vitro.	2001 Apr 23	11336796
(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
CB1 cannabinoid receptor-mediated neurite remodeling in mouse neuroblastoma N1E-115 cells.	2001 Aug 15	11494371
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
Endogenous cannabinoid, 2-arachidonoylglycerol, attenuates naloxone-precipitated withdrawal signs in morphine-dependent mice.	2001 Aug 3	11478928
Activation of the CB1 cannabinoid receptor protects cultured mouse spinal neurons against excitotoxicity.	2001 Aug 31	11514075
Differential role of the nitric oxide pathway on delta(9)-THC-induced central nervous system effects in the mouse.	2001 Feb	11168564
In vitro and in vivo pharmacological characterization of JTE-907, a novel selective ligand for cannabinoid CB2 receptor.	2001 Feb	11160626
The relative contributions of ecstasy and cannabis to cognitive impairment.	2001 Jan	11271410
[Characteristics of abnormal behavior induced by delta 9-tetrahydrocannabinol in rats].	2001 Jan	11233294
Separation of cannabinoid receptor affinity and efficacy in delta-8-tetrahydrocannabinol side-chain analogues.	2001 Jan	11159703
CB1 cannabinoid receptor inhibits synaptic release of glutamate in rat dorsolateral striatum.	2001 Jan	11152748
Dragon's Blood incense: misbranded as a drug of abuse?	2001 Jan 1	11056265
High rates of midazolam self-administration in squirrel monkeys.	2001 Jul	11548111
The pharmacological activity of inhalation exposure to marijuana smoke in mice.	2001 Jul 1	11376914
Involvement of somatodendritic 5-HT(1A) receptors in Delta(9)-tetrahydrocannabinol-induced hypothermia in the rat.	2001 Jul-Aug	11509221
Interaction between delta-9-tetrahydrocannabinol and indomethacin.	2001 Jul-Aug	11464074
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
Comparison of ELISAs for opiates, methamphetamine, cocaine metabolite, benzodiazepines, phencyclidine, and cannabinoids in whole blood and urine.	2001 Mar	11238309
The role of central and peripheral Cannabinoid1 receptors in the antihyperalgesic activity of cannabinoids in a model of neuropathic pain.	2001 May	11323130
Critical role of the endogenous cannabinoid system in mouse pup suckling and growth.	2001 May 11	11426843
Long term cerebroprotective effects of dexanabinol in a model of focal cerebral ischemia.	2001 May 18	11368967
[Passive exposure in detection of low blood and urine cannabinoid concentrations].	2001 May-Jun	11508050
Delta9-tetrahydrocannabivarin as a marker for the ingestion of marijuana versus Marinol: results of a clinical study.	2001 Oct	11599601
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
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
Marijuana abstinence effects in marijuana smokers maintained in their home environment.	2001 Oct	11576029
Ethanol increases plasma Delta(9)-tetrahydrocannabinol (THC) levels and subjective effects after marihuana smoking in human volunteers.	2001 Oct 1	11543984
Neuroprotection by Delta9-tetrahydrocannabinol, the main active compound in marijuana, against ouabain-induced in vivo excitotoxicity.	2001 Sep 1	11517236
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

Substance Class	Chemical Created by `admin` on `Fri Dec 16 15:56:25 UTC 2022` Edited by `admin` on `Fri Dec 16 15:56:25 UTC 2022`
Record UNII	7J8897W37S
Record Status	`Validated (UNII)`
Record Version

Download

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

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

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