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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 of DRONABINOL

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

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 TargetPharmacologyConditionPotency
3.13 nM [Ki]
5.05 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
MARINOL
Secondary
MARINOL
Secondary
MARINOL

Cmax

ValueDoseCo-administeredAnalytePopulation
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

ValueDoseCo-administeredAnalytePopulation
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

Funbound

ValueDoseCo-administeredAnalytePopulation
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

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

Drug as victim

PubMed

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