U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
8.29 null [pKi]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
CESAMET

Approved Use

Cesamet capsules are indicated for the treatment of the nausea and vomiting associated with cancer chemotherapy in patients who have failed to respond adequately to conventional antiemetic treatments. This restriction is required because a substantial proportion of any group of patients treated with Cesamet can be expected to experience disturbing psychotomimetic reactions not observed with other antiemetic agents. Because of its potential to alter the mental state, Cesamet is intended for use under circumstances that permit close supervision of the patient by a responsible individual particularly during initial use of Cesamet and during dose adjustments. Cesamet contains nabilone, which is controlled in Schedule II of the Controlled Substances Act. Schedule II substances have a high potential for abuse. Prescriptions for Cesamet should be limited to the amount necessary for a single cycle of chemotherapy (i.e., a few days). Cesamet capsules are not intended to be used on as needed basis or as a first antiemetic product prescribed for a patient. As with all controlled drugs, prescribers should monitor patients receiving nabilone for signs of excessive use, abuse and misuse. Patients who may be at increased risk for substance abuse include those with a personal or family history of substance abuse (including drug or alcohol abuse) or mental illness.

Launch Date

1985
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
345 ng × h/mL
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
NABILONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
90 ng × h/mL
0.5 mg single, intravenous
dose: 0.5 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
NABILONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2 h
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
NABILONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
1.7 h
0.5 mg single, intravenous
dose: 0.5 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
NABILONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
2 mg 1 times / day single, oral
Recommended
Dose: 2 mg, 1 times / day
Route: oral
Route: single
Dose: 2 mg, 1 times / day
Sources:
unhealthy, 18-77
n = 67
Health Status: unhealthy
Condition: cancer
Age Group: 18-77
Sex: M+F
Population Size: 67
Sources:
Disc. AE: Hallucinations...
AEs leading to
discontinuation/dose reduction:
Hallucinations
Sources:
2 mg 2 times / day multiple, oral
Recommended
Dose: 2 mg, 2 times / day
Route: oral
Route: multiple
Dose: 2 mg, 2 times / day
Sources: Page: Protocol 28
unhealthy, 20-78
n = 24
Health Status: unhealthy
Condition: cancer
Age Group: 20-78
Sex: M+F
Population Size: 24
Sources: Page: Protocol 28
Disc. AE: Intoxication, Orthostatic hypotension...
AEs leading to
discontinuation/dose reduction:
Intoxication
Orthostatic hypotension
Drowsiness
Dizziness
Sources: Page: Protocol 28
8 mg 1 times / day multiple, oral
Highest studied dose
Dose: 8 mg, 1 times / day
Route: oral
Route: multiple
Dose: 8 mg, 1 times / day
Sources:
healthy, 30±10
n = 11
Health Status: healthy
Age Group: 30±10
Sex: M+F
Population Size: 11
Sources:
AEs

AEs

AESignificanceDosePopulation
Hallucinations Disc. AE
2 mg 1 times / day single, oral
Recommended
Dose: 2 mg, 1 times / day
Route: oral
Route: single
Dose: 2 mg, 1 times / day
Sources:
unhealthy, 18-77
n = 67
Health Status: unhealthy
Condition: cancer
Age Group: 18-77
Sex: M+F
Population Size: 67
Sources:
Dizziness Disc. AE
2 mg 2 times / day multiple, oral
Recommended
Dose: 2 mg, 2 times / day
Route: oral
Route: multiple
Dose: 2 mg, 2 times / day
Sources: Page: Protocol 28
unhealthy, 20-78
n = 24
Health Status: unhealthy
Condition: cancer
Age Group: 20-78
Sex: M+F
Population Size: 24
Sources: Page: Protocol 28
Drowsiness Disc. AE
2 mg 2 times / day multiple, oral
Recommended
Dose: 2 mg, 2 times / day
Route: oral
Route: multiple
Dose: 2 mg, 2 times / day
Sources: Page: Protocol 28
unhealthy, 20-78
n = 24
Health Status: unhealthy
Condition: cancer
Age Group: 20-78
Sex: M+F
Population Size: 24
Sources: Page: Protocol 28
Intoxication Disc. AE
2 mg 2 times / day multiple, oral
Recommended
Dose: 2 mg, 2 times / day
Route: oral
Route: multiple
Dose: 2 mg, 2 times / day
Sources: Page: Protocol 28
unhealthy, 20-78
n = 24
Health Status: unhealthy
Condition: cancer
Age Group: 20-78
Sex: M+F
Population Size: 24
Sources: Page: Protocol 28
Orthostatic hypotension Disc. AE
2 mg 2 times / day multiple, oral
Recommended
Dose: 2 mg, 2 times / day
Route: oral
Route: multiple
Dose: 2 mg, 2 times / day
Sources: Page: Protocol 28
unhealthy, 20-78
n = 24
Health Status: unhealthy
Condition: cancer
Age Group: 20-78
Sex: M+F
Population Size: 24
Sources: Page: Protocol 28
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer






Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
PubMed

PubMed

TitleDatePubMed
Superiority of nabilone over prochlorperazine as an antiemetic in patients receiving cancer chemotherapy.
1979 Jun 7
Nabilone: an effective antiemetic in patients receiving cancer chemotherapy.
1981 Aug-Sep
Antiemetic efficacy of nabilone and dexamethasone: a randomized study of patients with lung cancer receiving chemotherapy.
1987 Aug
A randomized trial of oral nabilone and prochlorperazine compared to intravenous metoclopramide and dexamethasone in the treatment of nausea and vomiting induced by chemotherapy regimens containing cisplatin or cisplatin analogues.
1988 Apr
The cannabinoid CB1 receptor antagonist SR 141716A reverses the antiemetic and motor depressant actions of WIN 55, 212-2.
2001 Oct 26
Antiinflammatory action of endocannabinoid palmitoylethanolamide and the synthetic cannabinoid nabilone in a model of acute inflammation in the rat.
2002 Jan
Options for the prevention and management of acute chemotherapy-induced nausea and vomiting in children.
2003
Medical marijuana initiatives : are they justified? How successful are they likely to be?
2003
Therapeutic potential of cannabinoids in CNS disease.
2003
Cannabinoids for gastrointestinal diseases: potential therapeutic applications.
2003 Jan
Two cases of "cannabis acute psychosis" following the administration of oral cannabis.
2005 Apr 1
Pharmacokinetics of cannabinoids.
2005 Autumn
The effect of nabilone on neuropsychological functions related to driving ability: an extended case series.
2005 Jun
Cannabinoids in bipolar affective disorder: a review and discussion of their therapeutic potential.
2005 May
Cannabinoids in medicine: A review of their therapeutic potential.
2006 Apr 21
Effects of nabilone, a synthetic cannabinoid, on postoperative pain.
2006 Aug
The legal status of medical marijuana.
2006 Dec
Nabilone (Cesamet) for chemotherapy-induced nausea and vomiting.
2006 Dec 4
A pilot clinical study of Delta9-tetrahydrocannabinol in patients with recurrent glioblastoma multiforme.
2006 Jul 17
[Benefits of an add-on treatment with the synthetic cannabinomimetic nabilone on patients with chronic pain--a randomized controlled trial].
2006 Jun
Low dose treatment with the synthetic cannabinoid Nabilone significantly reduces spasticity-related pain : a double-blind placebo-controlled cross-over trial.
2006 Oct
Translation of nondopaminergic treatments for levodopa-induced dyskinesia from MPTP-lesioned nonhuman primates to phase IIa clinical studies: keys to success and roads to failure.
2006 Oct
Endocannabinoid system and synaptic plasticity: implications for emotional responses.
2007
Cannabinoids for postoperative analgesia?
2007 Feb
The boy who refused an IV: a case report of subcutaneous clodronate for bone pain in a child with Ewing Sarcoma.
2007 Mar 21
Cannabinoids in the treatment of chemotherapy-induced nausea and vomiting: beyond prevention of acute emesis.
2007 May
Symptomatic treatment of multiple sclerosis using cannabinoids: recent advances.
2007 Sep
Cannabinoid CB1 and CB2 receptor ligand specificity and the development of CB2-selective agonists.
2008
Analgesic and antihyperalgesic effects of nabilone on experimental heat pain.
2008 Apr
Current approaches to the treatment of Parkinson's disease.
2008 Aug
A review of nabilone in the treatment of chemotherapy-induced nausea and vomiting.
2008 Feb
Cannabinoids in the management of difficult to treat pain.
2008 Feb
Chemotherapy-and cancer-related nausea and vomiting.
2008 Jan
The cannabinoid receptor agonist nabilone for the treatment of dementia-related agitation.
2008 Jan
Comparison of analgesic effects and patient tolerability of nabilone and dihydrocodeine for chronic neuropathic pain: randomised, crossover, double blind study.
2008 Jan 26
Are cannabinoids a new treatment option for pain in patients with fibromyalgia?
2008 Jul
[What sense in cannabinoid use as regulated by Italian DM 18/04/07? Pharmacological and legal considerations].
2008 Jun
Adjunctive nabilone in cancer pain and symptom management: a prospective observational study using propensity scoring.
2008 Mar
Therapeutic use of Cannabis sativa on chemotherapy-induced nausea and vomiting among cancer patients: systematic review and meta-analysis.
2008 Sep
Analgesia in conjunction with normalisation of thermal sensation following deep brain stimulation for central post-stroke pain.
2009 Dec 15
Use of granisetron transdermal system in the prevention of chemotherapy-induced nausea and vomiting: a review.
2009 Dec 16
Whole plant cannabis extracts in the treatment of spasticity in multiple sclerosis: a systematic review.
2009 Dec 4
Management of postoperative nausea and vomiting: focus on palonosetron.
2009 Feb
Fungal biotransformation of cannabinoids: potential for new effective drugs.
2009 Mar
Cannabinoids, endocannabinoids, and related analogs in inflammation.
2009 Mar
A pilot study using nabilone for symptomatic treatment in Huntington's disease.
2009 Nov 15
Different forms of glycine- and GABA(A)-receptor mediated inhibitory synaptic transmission in mouse superficial and deep dorsal horn neurons.
2009 Nov 18
Regulation of synthetic cannabinoids.
2009 Nov 7
Examining the roles of cannabinoids in pain and other therapeutic indications: a review.
2010 Jan
Patents

Sample Use Guides

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
Created
by admin
on Fri Dec 15 16:25:48 GMT 2023
Edited
by admin
on Fri Dec 15 16:25:48 GMT 2023
Record UNII
2N4O9L084N
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NABILONE
INN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
NABILONE [MI]
Common Name English
NABILONE [VANDF]
Common Name English
nabilone [INN]
Common Name English
Nabilone [WHO-DD]
Common Name English
(±)-3-(1,1-DIMETHYLHEPTYL-6,6A.BETA.,7,8,10,10A.ALPHA.-HEXAHYDRO-1-HYDROXY-6,6-DIMETHYL-9H-DIBENZO(B,D)PYRAN-9-ONE
Common Name English
9H-DIBENZO(B,D)PYRAN-9-ONE, 3-(1,1-DIMETHYLHEPTYL)-6,6A,7,8,10,10A-HEXAHYDRO-1-HYDROXY-6,6-DIMETHYL-, TRANS-, (±)-
Common Name English
CESAMET
Brand Name English
NABILONE [ORANGE BOOK]
Common Name English
CPD-109514
Code English
NABILONE [USAN]
Common Name English
NABILONE [MART.]
Common Name English
CPD 109514
Code English
Classification Tree Code System Code
NCI_THESAURUS C267
Created by admin on Fri Dec 15 16:25:48 GMT 2023 , Edited by admin on Fri Dec 15 16:25:48 GMT 2023
LIVERTOX NBK547865
Created by admin on Fri Dec 15 16:25:48 GMT 2023 , Edited by admin on Fri Dec 15 16:25:48 GMT 2023
NDF-RT N0000008010
Created by admin on Fri Dec 15 16:25:48 GMT 2023 , Edited by admin on Fri Dec 15 16:25:48 GMT 2023
DEA NO. 7379
Created by admin on Fri Dec 15 16:25:48 GMT 2023 , Edited by admin on Fri Dec 15 16:25:48 GMT 2023
NDF-RT N0000175782
Created by admin on Fri Dec 15 16:25:48 GMT 2023 , Edited by admin on Fri Dec 15 16:25:48 GMT 2023
WHO-VATC QA04AD11
Created by admin on Fri Dec 15 16:25:48 GMT 2023 , Edited by admin on Fri Dec 15 16:25:48 GMT 2023
EU-Orphan Drug Nabilone
Created by admin on Fri Dec 15 16:25:48 GMT 2023 , Edited by admin on Fri Dec 15 16:25:48 GMT 2023
WHO-ATC A04AD11
Created by admin on Fri Dec 15 16:25:48 GMT 2023 , Edited by admin on Fri Dec 15 16:25:48 GMT 2023
Code System Code Type Description
PUBCHEM
5284592
Created by admin on Fri Dec 15 16:25:48 GMT 2023 , Edited by admin on Fri Dec 15 16:25:48 GMT 2023
PRIMARY
CAS
51022-71-0
Created by admin on Fri Dec 15 16:25:48 GMT 2023 , Edited by admin on Fri Dec 15 16:25:48 GMT 2023
PRIMARY
MERCK INDEX
m7697
Created by admin on Fri Dec 15 16:25:48 GMT 2023 , Edited by admin on Fri Dec 15 16:25:48 GMT 2023
PRIMARY Merck Index
ChEMBL
CHEMBL2218896
Created by admin on Fri Dec 15 16:25:48 GMT 2023 , Edited by admin on Fri Dec 15 16:25:48 GMT 2023
PRIMARY
SMS_ID
100000084425
Created by admin on Fri Dec 15 16:25:48 GMT 2023 , Edited by admin on Fri Dec 15 16:25:48 GMT 2023
PRIMARY
EVMPD
SUB09104MIG
Created by admin on Fri Dec 15 16:25:48 GMT 2023 , Edited by admin on Fri Dec 15 16:25:48 GMT 2023
PRIMARY
MESH
C011941
Created by admin on Fri Dec 15 16:25:48 GMT 2023 , Edited by admin on Fri Dec 15 16:25:48 GMT 2023
PRIMARY
FDA UNII
2N4O9L084N
Created by admin on Fri Dec 15 16:25:48 GMT 2023 , Edited by admin on Fri Dec 15 16:25:48 GMT 2023
PRIMARY
EPA CompTox
DTXSID8023341
Created by admin on Fri Dec 15 16:25:48 GMT 2023 , Edited by admin on Fri Dec 15 16:25:48 GMT 2023
PRIMARY
RXCUI
31447
Created by admin on Fri Dec 15 16:25:48 GMT 2023 , Edited by admin on Fri Dec 15 16:25:48 GMT 2023
PRIMARY RxNorm
DRUG BANK
DB00486
Created by admin on Fri Dec 15 16:25:48 GMT 2023 , Edited by admin on Fri Dec 15 16:25:48 GMT 2023
PRIMARY
INN
3930
Created by admin on Fri Dec 15 16:25:48 GMT 2023 , Edited by admin on Fri Dec 15 16:25:48 GMT 2023
PRIMARY
DAILYMED
2N4O9L084N
Created by admin on Fri Dec 15 16:25:48 GMT 2023 , Edited by admin on Fri Dec 15 16:25:48 GMT 2023
PRIMARY
NCI_THESAURUS
C1171
Created by admin on Fri Dec 15 16:25:48 GMT 2023 , Edited by admin on Fri Dec 15 16:25:48 GMT 2023
PRIMARY
DRUG CENTRAL
1862
Created by admin on Fri Dec 15 16:25:48 GMT 2023 , Edited by admin on Fri Dec 15 16:25:48 GMT 2023
PRIMARY
WIKIPEDIA
NABILONE
Created by admin on Fri Dec 15 16:25:48 GMT 2023 , Edited by admin on Fri Dec 15 16:25:48 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> AGONIST
Ki
TARGET -> AGONIST
Related Record Type Details
METABOLITE -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC