NABILONE

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 Search

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

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/018677s011lbl.pdf

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 Target	Pharmacology	Condition	Potency
Cannabinoid CB1 receptor 85 Target ID: CHEMBL218 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8981483	Partial Agonist 290		8.29 null [pKi]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Nausea and vomiting 19 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/018677s011lbl.pdf	Palliative		Approved 8429	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

Value	Dose	Co-administered	Analyte	Population
345 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/872500	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/872500	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/872500	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/872500	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

Dose	Population	Adverse 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/018677Orig1s000rev.pdf#36	unhealthy, 18-77 n = 67 Health Status: unhealthy Condition: cancer Age Group: 18-77 Sex: M+F Population Size: 67 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/018677Orig1s000rev.pdf#36	Disc. AE: Hallucinations... AEs leading to discontinuation/dose reduction: Hallucinations Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/018677Orig1s000rev.pdf#36
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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/018677Orig1s000rev.pdf#147 Page: Protocol 28	unhealthy, 20-78 n = 24 Health Status: unhealthy Condition: cancer Age Group: 20-78 Sex: M+F Population Size: 24 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/018677Orig1s000rev.pdf#147 Page: Protocol 28	Disc. AE: Intoxication, Orthostatic hypotension... AEs leading to discontinuation/dose reduction: Intoxication Orthostatic hypotension Drowsiness Dizziness Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/018677Orig1s000rev.pdf#147 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: https://pubmed.ncbi.nlm.nih.gov/23443718/	healthy, 30±10 n = 11 Health Status: healthy Age Group: 30±10 Sex: M+F Population Size: 11 Sources: https://pubmed.ncbi.nlm.nih.gov/23443718/	Sources: https://pubmed.ncbi.nlm.nih.gov/23443718/

AEs

AE	Significance	Dose	Population
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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/018677Orig1s000rev.pdf#36	unhealthy, 18-77 n = 67 Health Status: unhealthy Condition: cancer Age Group: 18-77 Sex: M+F Population Size: 67 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/018677Orig1s000rev.pdf#36
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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/018677Orig1s000rev.pdf#147 Page: Protocol 28	unhealthy, 20-78 n = 24 Health Status: unhealthy Condition: cancer Age Group: 20-78 Sex: M+F Population Size: 24 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/018677Orig1s000rev.pdf#147 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/018677Orig1s000rev.pdf#147 Page: Protocol 28	unhealthy, 20-78 n = 24 Health Status: unhealthy Condition: cancer Age Group: 20-78 Sex: M+F Population Size: 24 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/018677Orig1s000rev.pdf#147 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/018677Orig1s000rev.pdf#147 Page: Protocol 28	unhealthy, 20-78 n = 24 Health Status: unhealthy Condition: cancer Age Group: 20-78 Sex: M+F Population Size: 24 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/018677Orig1s000rev.pdf#147 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/018677Orig1s000rev.pdf#147 Page: Protocol 28	unhealthy, 20-78 n = 24 Health Status: unhealthy Condition: cancer Age Group: 20-78 Sex: M+F Population Size: 24 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/018677Orig1s000rev.pdf#147 Page: Protocol 28

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587	inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 CYP2A6 707 CYP2C19 1478 CYP2E1 882 CYP2C8 911	BCRP 561

Drug as perpetrator

Target	Modality	Activity
CYP2C8 965	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/018677s011lbl.pdf Page: 3.0	moderate [IC50 >10 uM]
CYP2C9 1819	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/018677s011lbl.pdf Page: 3.0	moderate [IC50 >10 uM]
CYP1A2 1692	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/018677s011lbl.pdf Page: 2.0	no
CYP2A6 739	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/018677s011lbl.pdf Page: 2.0	no
CYP2C19 1553	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/018677s011lbl.pdf Page: 2.0	no
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/018677s011lbl.pdf Page: 2.0	no
CYP2E1 970	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/018677s011lbl.pdf Page: 2.0	weak [IC50 >50 uM]
CYP3A4 1925	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/018677s011lbl.pdf Page: 2.0	weak [IC50 >50 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
BCRP 561	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/18339814/	yes

Sourcing

Vendor/Aggregator	ID	URL
ABI Chem	AC1NR4QM
Ambinter	Amb13889614	http://www.ambinter.com/reference/13889614
Aurora Fine Chemicals LLC	A17.902.715	http://online.aurorafinechemicals.com/info?ID=A17.902.715
BioSynth	N-0100	https://www.biosynth.com/products/biochemistry/other-biochemicals/products/N-0100.html
ChemMol	99099378	http://www.chemmol.com/chemmol/99099378.html
Chemieliva Pharmaceutical Co., Ltd	PBCM0606424
Compound Cloud	5284592
MuseChem	I008220	https://www.musechem.com/product/I008220.html
NovoSeek	5284592
OChem	18965	http://www.ocheminc.com/index.php?act=psearch&pid=022N710
Sigma Aldrich	N3785
Sigma Aldrich	N3785\|SIGMA
Sigma-Aldrich	N3785_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/n3785?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S536559	http://www.smolecule.com/products/s536559
THE BioTek	bt-275885	https://www.thebiotek.com/product/inhibitors/bt-275885
ZINC	ZINC000001542930	http://zinc15.docking.org/substances/ZINC000001542930
eMolecules	225773898

PubMed

Title	Date	PubMed
Superiority of nabilone over prochlorperazine as an antiemetic in patients receiving cancer chemotherapy.	1979 Jun 7	375088
Nabilone: an effective antiemetic in patients receiving cancer chemotherapy.	1981 Aug-Sep	6271844
Antiemetic efficacy of nabilone and dexamethasone: a randomized study of patients with lung cancer receiving chemotherapy.	1987 Aug	3039831
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	2838294
Cannabinoids in health and disease.	2007	18286801
[Cannabinoids in medicine].	2008	19165445
Cannabinoid CB1 and CB2 receptor ligand specificity and the development of CB2-selective agonists.	2008	18537620
Analgesic and antihyperalgesic effects of nabilone on experimental heat pain.	2008 Apr	18302810
Current approaches to the treatment of Parkinson's disease.	2008 Aug	19043519
A review of nabilone in the treatment of chemotherapy-induced nausea and vomiting.	2008 Feb	18728826
Cannabinoids in the management of difficult to treat pain.	2008 Feb	18728714
Chemotherapy-and cancer-related nausea and vomiting.	2008 Jan	18231647
Comparison of analgesic effects and patient tolerability of nabilone and dihydrocodeine for chronic neuropathic pain: randomised, crossover, double blind study.	2008 Jan 26	18182416
Nabilone for the treatment of paraneoplastic night sweats: a report of four cases.	2008 Jul	18715188
Are cannabinoids a new treatment option for pain in patients with fibromyalgia?	2008 Jul	18521112
[What sense in cannabinoid use as regulated by Italian DM 18/04/07? Pharmacological and legal considerations].	2008 Jun	18497729
Adjunctive nabilone in cancer pain and symptom management: a prospective observational study using propensity scoring.	2008 Mar	18402303
Chemotherapy-induced nausea and vomiting.	2008 Mar-Apr	18391612
Therapeutic use of Cannabis sativa on chemotherapy-induced nausea and vomiting among cancer patients: systematic review and meta-analysis.	2008 Sep	18625004
Tetrahydrocannabinol (Delta 9-THC) Treatment in Chronic Central Neuropathic Pain and Fibromyalgia Patients: Results of a Multicenter Survey.	2009	20798872
Identification of candidate genes affecting Delta9-tetrahydrocannabinol biosynthesis in Cannabis sativa.	2009	19581347
A treatment algorithm for neuropathic pain: an update.	2009 Dec	20156002
Analgesia in conjunction with normalisation of thermal sensation following deep brain stimulation for central post-stroke pain.	2009 Dec 15	19833434
Use of granisetron transdermal system in the prevention of chemotherapy-induced nausea and vomiting: a review.	2009 Dec 16	21188092
Whole plant cannabis extracts in the treatment of spasticity in multiple sclerosis: a systematic review.	2009 Dec 4	19961570
Management of postoperative nausea and vomiting: focus on palonosetron.	2009 Feb	19436621
Central side-effects of therapies based on CB1 cannabinoid receptor agonists and antagonists: focus on anxiety and depression.	2009 Feb	19285266
Emerging strategies for exploiting cannabinoid receptor agonists as medicines.	2009 Feb	19226257
Fungal biotransformation of cannabinoids: potential for new effective drugs.	2009 Mar	19333876
Cannabinoids, endocannabinoids, and related analogs in inflammation.	2009 Mar	19199042
A pilot study using nabilone for symptomatic treatment in Huntington's disease.	2009 Nov 15	19845035
Different forms of glycine- and GABA(A)-receptor mediated inhibitory synaptic transmission in mouse superficial and deep dorsal horn neurons.	2009 Nov 18	19919721
Regulation of synthetic cannabinoids.	2009 Nov 7	19897126
Cannabinoids as pharmacotherapies for neuropathic pain: from the bench to the bedside.	2009 Oct	19789075
The use of a synthetic cannabinoid in the management of treatment-resistant nightmares in posttraumatic stress disorder (PTSD).	2009 Winter	19228182
Receptors and channels targeted by synthetic cannabinoid receptor agonists and antagonists.	2010	20166927
Optimizing emetic control in children receiving antineoplastic therapy: beyond the guidelines.	2010	20034341
The effects of nabilone on sleep in fibromyalgia: results of a randomized controlled trial.	2010 Feb 1	20007734
Examining the roles of cannabinoids in pain and other therapeutic indications: a review.	2010 Jan	20001426
Pharmacology and toxicology of Cannabis derivatives and endocannabinoid agonists.	2010 Jan	19832688
Functional role of cannabinoid receptors in urinary bladder.	2010 Jan-Mar	20535281
Chemoenzymatic synthesis and cannabinoid activity of a new diazabicyclic amide of phenylacetylricinoleic acid.	2010 Jun 1	20457524
The abuse potential of the synthetic cannabinoid nabilone.	2010 Mar	20402993
Cannabinoid-mediated modulation of neuropathic pain and microglial accumulation in a model of murine type I diabetic peripheral neuropathic pain.	2010 Mar 17	20236533
New approaches in the management of spasticity in multiple sclerosis patients: role of cannabinoids.	2010 Mar 3	20234785
A randomized, double-blinded, crossover pilot study assessing the effect of nabilone on spasticity in persons with spinal cord injury.	2010 May	20434606
Nabilone produces marked impairments to cognitive function and changes in subjective state in healthy volunteers.	2010 Nov	19525335
Using cannabinoids in pain and palliative care.	2010 Oct	20972379
Treatment of Irritability in Huntington's Disease.	2010 Sep	20730109
Substitution profile of the cannabinoid agonist nabilone in human subjects discriminating δ9-tetrahydrocannabinol.	2010 Sep-Oct	20838217

Patents

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

Name

Type

Language

NABILONE

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