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Details

Stereochemistry RACEMIC
Molecular Formula C24H36O3
Molecular Weight 372.5408
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NABILONE

SMILES

[H][C@@]12CC(=O)CC[C@@]1([H])C(C)(C)OC3=C2C(O)=CC(=C3)C(C)(C)CCCCCC

InChI

InChIKey=GECBBEABIDMGGL-RTBURBONSA-N
InChI=1S/C24H36O3/c1-6-7-8-9-12-23(2,3)16-13-20(26)22-18-15-17(25)10-11-19(18)24(4,5)27-21(22)14-16/h13-14,18-19,26H,6-12,15H2,1-5H3/t18-,19-/m1/s1

HIDE SMILES / InChI

Molecular Formula C24H36O3
Molecular Weight 372.5408
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

Nabilone is a synthetic cannabinoid approved under the brand name cesamet for treatment of severe nausea and vomiting associated with cancer chemotherapy. Nabilone is an orally active which, like other cannabinoids, has complex effects on the central nervous system (CNS). It has been suggested that the antiemetic effect of nabilone is caused by interaction with the cannabinoid receptor system, i.e. the CB (1) receptor, which has been discovered in neural tissues.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
8.29 null [pKi]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
CESAMET

AUC

ValueDoseCo-administeredAnalytePopulation
345 ng × h/mL
2 mg single, oral
NABILONE plasma
Homo sapiens
90 ng × h/mL
0.5 mg single, intravenous
NABILONE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
2 h
2 mg single, oral
NABILONE plasma
Homo sapiens
1.7 h
0.5 mg single, intravenous
NABILONE plasma
Homo sapiens

Doses

AEs

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer






Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
The usual adult dosage is 1 or 2 mg b.i.d. On the day of chemotherapy, the initial dose should be given 1 to 3 hours before the chemotherapeutic agent is administered. To minimize side effects, it is recommended that the lower starting dose be used and that the dose be increased as necessary. A dose of 1 or 2 mg the night before may be useful. The maximum recommended daily dose is 6 mg given in divided doses t.i.d. Cesamet (nabilone) may be administered 2 or 3 times daily during the entire course of each cycle of chemotherapy and, if needed, for 48 hours after the last dose of each cycle of chemotherapy.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Record UNII
2N4O9L084N
Record Status Validated (UNII)
Record Version