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Nabilone

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Also known as CesametCPD 109514CPD-109514Nabilonarel-Nabilone

Summary

Nabilone (CHEMBL2218896) is an approved small molecule (ATC A04AD11) targeting CNR1 and CNR2; indicated across 13 conditions including neoplasm and diabetic neuropathy.

At a glance

  • Status: Approved (max clinical phase 4)
  • Modality: Small molecule
  • ATC class: A04AD11
  • Targets: 2 (CNR1, CNR2)
  • Indications: 13 conditions
  • Clinical trials: 29
  • Chemistry: 372.5 Da · C24H36O3

Identifiers

Drug identity and classification

FieldValue
ChEMBL IDCHEMBL2218896
NameNabilone
TypeSmall molecule
Max phase4
FDA approvedno
PubChem CID39860
ATCA04AD11
Molecular formulaC24H36O3
Molecular weight372.5
InChIKeyGECBBEABIDMGGL-UHFFFAOYSA-N

SMILES: CCCCCCC(C)(C)C1=CC(=C2C3CC(=O)CCC3C(OC2=C1)(C)C)O

IUPAC name: 1-hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-7,8,10,10a-tetrahydro-6aH-benzo[c]chromen-9-one

Also known as: Cesamet, CPD 109514, CPD-109514, Nabilona, Nabilone, NABILONE, nabilone, rel-Nabilone

Patent coverage: 109 distinct patent families (181 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 161 (89%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

GeneTargetActionpAffinityCancer dependencyUniProt
CNR1CB1 receptorAgonist8.40%P21554
CNR2CB2 receptorAgonist8.2P34972

Broader ChEMBL bioactivity targets: 7 (assay-derived). Sample: Cannabinoid receptor 1, Sodium-dependent dopamine transporter, Cannabinoid receptor 2, Adenosine receptor A3, Nuclear receptor subfamily 1 group I member 2, Cannabinoid receptor 1, Cannabinoid receptor 2.

Bioactivity

ChEMBL activities: 17 potent at pChembl ≥ 5 of 18 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

TargetpChemblTypeValueUnitActivity ID
P479368.74Ki1.8nMCHEMBL_ACT_3508873
CNR28.73Ki1.84nMCHEMBL_ACT_14573961
CNR28.73Ki1.84nMCHEMBL_ACT_467076
CNR18.66Ki2.19nMCHEMBL_ACT_14573966
P202728.66Ki2.2nMCHEMBL_ACT_3508857
CNR18.66Ki2.19nMCHEMBL_ACT_467077
CNR18.4EC503.98nMCHEMBL_ACT_3413907
CNR18.4Ki3.98nMCHEMBL_ACT_6366815
CNR18.4EC503.98nMCHEMBL_ACT_6366851
CNR18.29Ki5.1nMCHEMBL_ACT_3413906
CNR28.2Ki6.31nMCHEMBL_ACT_6366827
CNR27.8EC5015.85nMCHEMBL_ACT_6366864
CNR27.75Ki17.6nMCHEMBL_ACT_3413908
CNR16.78AC50167.7nMCHEMBL_ACT_25231828
NR1I25.6AC502500nMCHEMBL_ACT_25188375
NR1I25.48AC503300nMCHEMBL_ACT_25224477
ADORA35.04AC509100nMCHEMBL_ACT_25134491

Target pathways

Aggregated over 2 target gene(s): CNR1, CNR2.

Top Reactome pathways

2 total, by targets touching each:

PathwayTargetsGenes
Class A/1 (Rhodopsin-like receptors)2CNR1, CNR2
G alpha (i) signalling events2CNR1, CNR2

Dominant GO biological processes

GO termTargets
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messenger2
adenylate cyclase-activating G protein-coupled receptor signaling pathway2
cannabinoid signaling pathway2
signal transduction2
G protein-coupled receptor signaling pathway2
adenylate cyclase-modulating G protein-coupled receptor signaling pathway1
axonal fasciculation1
glucose homeostasis1
retrograde trans-synaptic signaling by endocannabinoid1
regulation of presynaptic cytosolic calcium ion concentration1
response to amphetamine1
inflammatory response1
immune response1
leukocyte chemotaxis1
negative regulation of synaptic transmission, GABAergic1

Indications & clinical

Indications

13 indications (4 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

IndicationTrial phaseMONDOEFO
neoplasm4MONDO:0005070MONDO:0004992
diabetic neuropathy3MONDO:0006626EFO:1000783
Parkinson disease3MONDO:0005180MONDO:0005180
fibromyalgia2MONDO:0005546EFO:0005687
neuralgia2MONDO:0021667EFO:0005762
cannabis dependence2MONDO:0005689EFO:0007191
obesity disorder2MONDO:0011122EFO:0001073
obsessive-compulsive disorder1MONDO:0008114EFO:0004242

5 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 29.

Phase distribution

PhaseTrials
PHASE210
PHASE35
PHASE43
PHASE2/PHASE33
PHASE1/PHASE23
Not specified3
PHASE12

Top trials by phase / activity

NCTPhaseStatusTitle
NCT00418678PHASE4TERMINATEDA Phase IV Trial of Cesamet™ Given With Standard Antiemetic Therapy for Chemotherapy-induced Nausea and Vomiting
NCT00480181PHASE4COMPLETEDEfficacy and Safety Evaluation of Nabilone as Adjunctive Therapy to Gabapentin for the Management of Neuropathic Pain in Multiple Sclerosis
NCT05885685PHASE4COMPLETEDInvestigating the Effects of Nabilone on Endocannabinoid Metabolism
NCT04516057PHASE3RECRUITINGNabilone for Agitation Blinded Intervention Trial
NCT01035281PHASE3UNKNOWNEfficacy Study of Nabilone in the Treatment of Diabetic Peripheral Neuropathic Pain
NCT01347762PHASE2/PHASE3COMPLETEDNabilone for Cannabis Dependence: A Pilot Study
NCT02351882PHASE2/PHASE3COMPLETEDSafety and Efficacy of Nabilone in Alzheimer’s Disease
NCT02802540PHASE2/PHASE3UNKNOWNNabilone Effect on the Attenuation of Anorexia, Nutritional Status and Quality of Life in Lung Cancer Patients
NCT03773796PHASE3COMPLETEDNabilone for Non-motor Symptoms in Parkinson’s Disease
NCT04057456PHASE3COMPLETEDCannabinoids and an Anti-inflammatory Diet for the Treatment of Neuropathic Pain After Spinal Cord Injury
NCT05180968PHASE3COMPLETEDDIalysis Symptom COntrol-Pruritus Outcome Trial
NCT05742698PHASE2RECRUITINGNabilone for Agitation in Frontotemporal Dementia
NCT00272207PHASE2COMPLETEDA Trial Assessing the Effect of Nabilone on Pain and Quality of Life in Patients With Fibromyalgia
NCT00384410PHASE2UNKNOWNUse of the Cannabinoid Nabilone for the Promotion of Sleep in Chronic, Non-Malignant Pain Patients
NCT00699634PHASE2COMPLETEDNabilone for the Treatment of Phantom Limb Pain
NCT01222468PHASE2COMPLETEDEffect of Cannabinoids on Spasticity and Neuropathic Pain in Spinal Cord Injured Persons
NCT02115529PHASE2COMPLETEDStudy of Prevention of Postoperative Nausea and Vomiting Using Cesamet
NCT02911324PHASE1/PHASE2COMPLETEDCannabinoid Medication for Adults With OCD
NCT03251326PHASE1/PHASE2TERMINATEDNabilone in Cannabis Users With PTSD
NCT03769896PHASE2COMPLETEDNabilone for Non-motor Symptoms in Parkinson’s Disease
NCT04801641PHASE2TERMINATEDA Pilot Trial of Nabilone for the Treatment of Obesity
NCT04807829PHASE2WITHDRAWNAdjunctive CB1 Agonist Nabilone in Inpatients With Active Suicidal Ideation
NCT04880278PHASE1/PHASE2WITHDRAWNMultimodal Assessment of Cannabinoid Target Engagement in Adults With Obsessive-Compulsive Disorder
NCT05494437PHASE2COMPLETEDEffect of PP-01 on Cannabis Withdrawal Syndrome
NCT01517100PHASE1COMPLETEDThe Role of Endocannabinoids in Insulin Production and Action
NCT05273320PHASE1COMPLETEDClinical Trial of Nabilone for Aggression in Adults With Intellectual and Developmental Disabilities
NCT00381199Not specifiedCOMPLETEDNabilone Versus Amitriptyline in Improving Quality of Sleep in Patients With Fibromyalgia
NCT03210766Not specifiedCOMPLETEDNabilone and THC/CBD for the Treatment of FBSS Refractory Pain
NCT03422861Not specifiedUNKNOWNNabilone Use For Acute Pain in Inflammatory Bowel Disease Patients

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No PharmGKB pharmacogenomic data curated for this drug.

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

128 molecules share ≥1 primary target. Top 60 by shared-target count:

MoleculeSourceStatusShared targets
CANNABIDIOLChEMBLPhase 4 (approved)CNR1, CNR2
DRONABINOLChEMBLPhase 4 (approved)CNR1, CNR2
RIMONABANTChEMBLPhase 4 (approved)CNR1, CNR2
CANNABINOLChEMBLPhase 3CNR1, CNR2
DEXANABINOLChEMBLPhase 3CNR1, CNR2
EPIGALOCATECHIN GALLATEChEMBLPhase 3CNR1, CNR2
LENABASUMChEMBLPhase 3CNR1, CNR2
OTENABANTChEMBLPhase 3CNR1, CNR2
TARANABANTChEMBLPhase 3CNR1, CNR2
CANNABIDIVARINChEMBLPhase 2CNR1, CNR2
CANNABIGEROLChEMBLPhase 2CNR1, CNR2
DELTA-8-TETRAHYDROCANNABINOLChEMBLPhase 2CNR1, CNR2
IBIPINABANTChEMBLPhase 2CNR1, CNR2
PRS-211375ChEMBLPhase 2CNR1, CNR2
REDAFAMDASTATChEMBLPhase 2CNR1, CNR2
S-777469ChEMBLPhase 2CNR1, CNR2
SURINABANTChEMBLPhase 2CNR1, CNR2
TEDALINABChEMBLPhase 2CNR1, CNR2
TETRAHYDROCANNABIVARINChEMBLPhase 2CNR1, CNR2
TAFAMIDISChEMBL + PubChemPhase 4 (approved)CNR1
ACARBOSEChEMBLPhase 4 (approved)CNR1
ALCLOMETASONE DIPROPIONATEChEMBLPhase 4 (approved)CNR1
ALPRAZOLAMChEMBLPhase 4 (approved)CNR1
AMCINONIDEChEMBLPhase 4 (approved)CNR1
AMPRENAVIRChEMBLPhase 4 (approved)CNR1
ATENOLOLChEMBLPhase 4 (approved)CNR1
BECLOMETHASONE DIPROPIONATEChEMBLPhase 4 (approved)CNR1
BEPRIDILChEMBLPhase 4 (approved)CNR1
BIFONAZOLEChEMBLPhase 4 (approved)CNR1
BUCLIZINEChEMBLPhase 4 (approved)CNR1
BUSPIRONEChEMBLPhase 4 (approved)CNR1
CAFFEINEChEMBLPhase 4 (approved)CNR1
CALCITRIOLChEMBLPhase 4 (approved)CNR1
CANDESARTAN CILEXETILChEMBLPhase 4 (approved)CNR1
CARBENOXOLONEChEMBLPhase 4 (approved)CNR1
CEFDINIRChEMBLPhase 4 (approved)CNR1
CHLORHEXIDINEChEMBLPhase 4 (approved)CNR1
CICLESONIDEChEMBLPhase 4 (approved)CNR1
DEXAMETHASONEChEMBLPhase 4 (approved)CNR1
ECONAZOLEChEMBLPhase 4 (approved)CNR1
EFAVIRENZChEMBLPhase 4 (approved)CNR1
ENZALUTAMIDEChEMBLPhase 4 (approved)CNR1
ERYTHROMYCINChEMBLPhase 4 (approved)CNR1
ETHAMBUTOLChEMBLPhase 4 (approved)CNR1
FELODIPINEChEMBLPhase 4 (approved)CNR1
FENOFIBRATEChEMBLPhase 4 (approved)CNR1
FENTICONAZOLEChEMBLPhase 4 (approved)CNR1
FEXOFENADINEChEMBLPhase 4 (approved)CNR1
FLUOXETINEChEMBLPhase 4 (approved)CNR1
FLUSPIRILENEChEMBLPhase 4 (approved)CNR1
FLUTICASONE FUROATEChEMBLPhase 4 (approved)CNR1
GLIPIZIDEChEMBLPhase 4 (approved)CNR1
IMIPRAMINEChEMBLPhase 4 (approved)CNR1
INDOCYANINE GREEN ACID FORMChEMBLPhase 4 (approved)CNR1
KETOTIFENChEMBLPhase 4 (approved)CNR1
LOFEPRAMINEChEMBLPhase 4 (approved)CNR1
LORCASERINChEMBLPhase 4 (approved)CNR1
LOSARTANChEMBLPhase 4 (approved)CNR1
MASOPROCOLChEMBLPhase 4 (approved)CNR1
MECLIZINEChEMBLPhase 4 (approved)CNR1

About this page

Generated deterministically by Sugi Atlas from primary biomedical databases via BioBTree. Every record on this page traces to a primary source.

Generated
Atlas version
v1.1.2
BioBTree
v2.0.2

Sources 30

This page pulls from 30 datasets indexed by BioBTree:

chebichembl_activitychembl_moleculechembl_targetcivic_evidenceclingen_dosageclinical_trialsdepmapefoensemblentrezgogoparentgtopdbgtopdb_interactiongtopdb_ligandhgncmeshmondomsigdbpatent_compoundpharmgkbpharmgkb_guidelinepubchempubchem_activityreactomereactomeparentrefseqtranscriptuniprot