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

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

HIDE SMILES / InChI

Molecular Formula	C21H30O2
Molecular Weight	314.4617
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

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 28	Agonist 2,752		3.13 nM [Ki]
Cannabinoid receptor 1 33	Agonist 2,752		5.05 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Anorexia in AIDS 3	Primary	Approved 8,583	MARINOL
Vomiting in cancer chemotherapy 3	Secondary	Approved 8,583	MARINOL
Nausea in cancer chemotherapy 3	Secondary	Approved 8,583	MARINOL

C_max

Value	Dose	Analyte	Population
1.32 ng/mL	2.5 mg 2 times / day multiple, oral	DRONABINOL plasma	Homo sapiens
2.96 ng/mL	5 mg 2 times / day multiple, oral	DRONABINOL plasma	Homo sapiens
7.88 ng/mL	10 mg 2 times / day multiple, oral	DRONABINOL plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
2.88 ng × h/mL	2.5 mg 2 times / day multiple, oral	DRONABINOL plasma	Homo sapiens
6.16 ng × h/mL	5 mg 2 times / day multiple, oral	DRONABINOL plasma	Homo sapiens
15.2 ng × h/mL	10 mg 2 times / day multiple, oral	DRONABINOL plasma	Homo sapiens

F_unbound

Value	Dose	Analyte	Population
3%	2.5 mg 2 times / day multiple, oral	DRONABINOL plasma	Homo sapiens
3%	5 mg 2 times / day multiple, oral	DRONABINOL plasma	Homo sapiens
3%	10 mg 2 times / day multiple, oral	DRONABINOL plasma	Homo sapiens

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,946	substrate 1,193

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A1 132		CYP1A1 151

Drug as perpetrator

Show entries

Target	Modality	Activity	Metabolite	Clinical evidence
CYP1A1 272	inhibitor 4,027	likely
CYP1A1 272	inducer 1,966	yes

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Drug as victim

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Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 1,946	substrate 4,014	yes
CYP2C9 1,193	substrate 4,014	yes		yes (pharmacogenomic study)

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Sourcing

Sourcing

Show entries

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
BenchChem	B526632	https://www.benchchem.com/product/b526632
BOC Sciences	26514	https://www.bocsci.com/product/delta-9-tetrahydrocannabinol-cas-1972-08-3-334884.html

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PubMed

Show entries

Title	Date	PubMed
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
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
Cerebellar CB(1) receptor mediation of Delta(9)-THC-induced motor incoordination and its potentiation by ethanol and modulation by the cerebellar adenosinergic A(1) receptor in the mouse.	2000 May 12	10802025
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

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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