Taranabant

Summary

Taranabant (CHEMBL220360) is a phase-3 clinical-stage small molecule targeting CNR1 and CNR2; indicated across 4 conditions including obesity disorder and type 2 diabetes mellitus.

At a glance

• Status: Max clinical phase 3 (not approved)
• Modality: Small molecule
• Targets: 2 (CNR1, CNR2)
• Indications: 4 conditions
• Clinical trials: 9
• Chemistry: 516 Da · C27H25ClF3N3O2

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL220360
Name	Taranabant
Type	Small molecule
Max phase	3
FDA approved	no
PubChem CID	11226090
Molecular formula	C27H25ClF3N3O2
Molecular weight	516
InChIKey	QLYKJCMUNUWAGO-GAJHUEQPSA-N

SMILES: C[C@@H]([C@@H](CC1=CC=C(C=C1)Cl)C2=CC=CC(=C2)C#N)NC(=O)C(C)(C)OC3=NC=C(C=C3)C(F)(F)F

IUPAC name: N-[(2S,3S)-4-(4-chlorophenyl)-3-(3-cyanophenyl)butan-2-yl]-2-methyl-2-[[5-(trifluoromethyl)-2-pyridinyl]oxy]propanamide

Also known as: L-796568, Mk-0364, MK-0634, Mk0364, MK0634, Taranabant, taranabant, Taranbant, TARANABANT

Patent coverage: 249 distinct patent families (612 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 611 (100%) 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).

Gene	Target	Action	pAffinity	Cancer dependency	UniProt
CNR1	CB1 receptor	Inverse agonist	9.52	0%	P21554
CNR2	CB2 receptor		6.54		P34972

Broader ChEMBL bioactivity targets: 6 (assay-derived). Sample: Cannabinoid receptor 1, Voltage-gated inwardly rectifying potassium channel KCNH2, Cannabinoid receptor 2, Cytochrome P450 2D6, Cytochrome P450 2C9, Cannabinoid receptor 1.

Bioactivity

ChEMBL activities: 31 potent at pChembl ≥ 5 of 32 total. Top 100 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
CNR1	10.03	IC50	0.09	nM	CHEMBL_ACT_2155836
CNR1	9.54	IC50	0.29	nM	CHEMBL_ACT_2556681
CNR1	9.52	IC50	0.3	nM	CHEMBL_ACT_13970344
CNR1	9.52	IC50	0.3	nM	CHEMBL_ACT_1796864
CNR1	9.52	IC50	0.3	nM	CHEMBL_ACT_1912119
CNR1	9.52	IC50	0.3	nM	CHEMBL_ACT_20654732
CNR1	9.52	IC50	0.3	nM	CHEMBL_ACT_2156451
CNR1	9.52	IC50	0.3	nM	CHEMBL_ACT_2518740
CNR1	9.52	Ki	0.3	nM	CHEMBL_ACT_2690991
CNR1	9.52	IC50	0.3	nM	CHEMBL_ACT_3006988
CNR1	9.52	IC50	0.3	nM	CHEMBL_ACT_3242854
CNR1	9.52	IC50	0.3	nM	CHEMBL_ACT_3295821
CNR1	9.52	IC50	0.3	nM	CHEMBL_ACT_3314844
P20272	9.52	IC50	0.3	nM	CHEMBL_ACT_6307669
CYP2D6	9.23	IC50	0.59	nM	CHEMBL_ACT_3426713
CNR1	9.13	IC50	0.74	nM	CHEMBL_ACT_2155809
CNR1	9.13	IC50	0.74	nM	CHEMBL_ACT_3383552
P20272	9.07	IC50	0.86	nM	CHEMBL_ACT_2398698
CYP2C9	9.03	IC50	0.93	nM	CHEMBL_ACT_3426714
CNR1	8.92	IC50	1.2	nM	CHEMBL_ACT_2155812
CNR1	8.62	EC50	2.4	nM	CHEMBL_ACT_1796918
CNR1	8.62	EC50	2.4	nM	CHEMBL_ACT_3007048
CNR1	8.31	IC50	4.9	nM	CHEMBL_ACT_2155811
CNR1	8.3	IC50	5	nM	CHEMBL_ACT_2155810
CNR1	7.72	IC50	19	nM	CHEMBL_ACT_2155813
CNR1	7.66	IC50	22	nM	CHEMBL_ACT_2155814
CNR2	6.54	IC50	290	nM	CHEMBL_ACT_1796889
CNR2	6.54	Ki	290	nM	CHEMBL_ACT_2690992
CNR2	6.54	IC50	285	nM	CHEMBL_ACT_3006989
CNR2	6.54	IC50	290	nM	CHEMBL_ACT_3295822
CNR2	5.93	IC50	1170	nM	CHEMBL_ACT_2398661

Target pathways

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

Top Reactome pathways

2 total, by targets touching each:

Pathway	Targets	Genes
Class A/1 (Rhodopsin-like receptors)	2	CNR1, CNR2
G alpha (i) signalling events	2	CNR1, CNR2

Dominant GO biological processes

GO term	Targets
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messenger	2
adenylate cyclase-activating G protein-coupled receptor signaling pathway	2
cannabinoid signaling pathway	2
signal transduction	2
G protein-coupled receptor signaling pathway	2
adenylate cyclase-modulating G protein-coupled receptor signaling pathway	1
axonal fasciculation	1
glucose homeostasis	1
retrograde trans-synaptic signaling by endocannabinoid	1
regulation of presynaptic cytosolic calcium ion concentration	1
response to amphetamine	1
inflammatory response	1
immune response	1
leukocyte chemotaxis	1
negative regulation of synaptic transmission, GABAergic	1

Indications & clinical

Indications

3 diseases in clinical trials (phase 1–3, investigational — not approved indications). Highest ChEMBL trial phase per disease; a non-cancer approved use is occasionally logged at phase 3 here.

Disease (in trials)	Phase	MONDO	EFO
obesity disorder	3	MONDO:0011122	EFO:0001073
type 2 diabetes mellitus	3	MONDO:0005148	MONDO:0005148
nicotine dependence	2	MONDO:0008575	EFO:0003768

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

Clinical trials

Total trials: 9.

Phase distribution

Phase	Trials
PHASE3	5
PHASE2	3
PHASE2/PHASE3	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT00131391	PHASE3	TERMINATED	A Study of MK0364 in Obese Patients (0364-014)
NCT00131404	PHASE3	TERMINATED	A Two Year Safety and Efficacy Study in Obese Patients (0364-015)(TERMINATED)
NCT00131430	PHASE2/PHASE3	COMPLETED	An Eighteen Month Efficacy and Safety Study in Obese Patients (0364-020)(COMPLETED)
NCT00384605	PHASE3	TERMINATED	An Investigational Drug Study to Assess Weight Loss in Obese and Overweight Patients (0364-037)(TERMINATED)
NCT00420589	PHASE3	TERMINATED	A Weight Maintenance Study in Obese Patients (0364-012)(TERMINATED)
NCT00430742	PHASE3	TERMINATED	An Investigational Drug Study to Assess Weight Loss in Patients With Type 2 Diabetes Mellitus (0364-011)(TERMINATED)
NCT00109135	PHASE2	COMPLETED	A Study to Investigate a Research Drug as an Aid for Smoking Cessation in Chronic Cigarette Smokers (0364-007)
NCT00109148	PHASE2	COMPLETED	An Investigational Drug Study in Obese (Considerably Overweight) Patients (0364-006)
NCT00231790	PHASE2	COMPLETED	A Placebo-Controlled Study of MK0634 in Patients With Overactive Bladder (0634-007)

Clinical evidence (CIViC)

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

Pharmacology

Pharmacogenomics

No PharmGKB pharmacogenomic data curated for this drug.

Related molecules

Related molecules

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 100 by shared-target count:

Molecule	Source	Status	Shared targets
CANNABIDIOL	ChEMBL	Phase 4 (approved)	CNR1, CNR2
DRONABINOL	ChEMBL	Phase 4 (approved)	CNR1, CNR2
NABILONE	ChEMBL	Phase 4 (approved)	CNR1, CNR2
RIMONABANT	ChEMBL	Phase 4 (approved)	CNR1, CNR2
CANNABINOL	ChEMBL	Phase 3	CNR1, CNR2
DEXANABINOL	ChEMBL	Phase 3	CNR1, CNR2
EPIGALOCATECHIN GALLATE	ChEMBL	Phase 3	CNR1, CNR2
LENABASUM	ChEMBL	Phase 3	CNR1, CNR2
OTENABANT	ChEMBL	Phase 3	CNR1, CNR2
CANNABIDIVARIN	ChEMBL	Phase 2	CNR1, CNR2
CANNABIGEROL	ChEMBL	Phase 2	CNR1, CNR2
DELTA-8-TETRAHYDROCANNABINOL	ChEMBL	Phase 2	CNR1, CNR2
IBIPINABANT	ChEMBL	Phase 2	CNR1, CNR2
PRS-211375	ChEMBL	Phase 2	CNR1, CNR2
REDAFAMDASTAT	ChEMBL	Phase 2	CNR1, CNR2
S-777469	ChEMBL	Phase 2	CNR1, CNR2
SURINABANT	ChEMBL	Phase 2	CNR1, CNR2
TEDALINAB	ChEMBL	Phase 2	CNR1, CNR2
TETRAHYDROCANNABIVARIN	ChEMBL	Phase 2	CNR1, CNR2
TAFAMIDIS	ChEMBL + PubChem	Phase 4 (approved)	CNR1
ACARBOSE	ChEMBL	Phase 4 (approved)	CNR1
ALCLOMETASONE DIPROPIONATE	ChEMBL	Phase 4 (approved)	CNR1
ALPRAZOLAM	ChEMBL	Phase 4 (approved)	CNR1
AMCINONIDE	ChEMBL	Phase 4 (approved)	CNR1
AMPRENAVIR	ChEMBL	Phase 4 (approved)	CNR1
ATENOLOL	ChEMBL	Phase 4 (approved)	CNR1
BECLOMETHASONE DIPROPIONATE	ChEMBL	Phase 4 (approved)	CNR1
BEPRIDIL	ChEMBL	Phase 4 (approved)	CNR1
BIFONAZOLE	ChEMBL	Phase 4 (approved)	CNR1
BUCLIZINE	ChEMBL	Phase 4 (approved)	CNR1
BUSPIRONE	ChEMBL	Phase 4 (approved)	CNR1
CAFFEINE	ChEMBL	Phase 4 (approved)	CNR1
CALCITRIOL	ChEMBL	Phase 4 (approved)	CNR1
CANDESARTAN CILEXETIL	ChEMBL	Phase 4 (approved)	CNR1
CARBENOXOLONE	ChEMBL	Phase 4 (approved)	CNR1
CEFDINIR	ChEMBL	Phase 4 (approved)	CNR1
CHLORHEXIDINE	ChEMBL	Phase 4 (approved)	CNR1
CICLESONIDE	ChEMBL	Phase 4 (approved)	CNR1
DEXAMETHASONE	ChEMBL	Phase 4 (approved)	CNR1
ECONAZOLE	ChEMBL	Phase 4 (approved)	CNR1
EFAVIRENZ	ChEMBL	Phase 4 (approved)	CNR1
ENZALUTAMIDE	ChEMBL	Phase 4 (approved)	CNR1
ERYTHROMYCIN	ChEMBL	Phase 4 (approved)	CNR1
ETHAMBUTOL	ChEMBL	Phase 4 (approved)	CNR1
FELODIPINE	ChEMBL	Phase 4 (approved)	CNR1
FENOFIBRATE	ChEMBL	Phase 4 (approved)	CNR1
FENTICONAZOLE	ChEMBL	Phase 4 (approved)	CNR1
FEXOFENADINE	ChEMBL	Phase 4 (approved)	CNR1
FLUOXETINE	ChEMBL	Phase 4 (approved)	CNR1
FLUSPIRILENE	ChEMBL	Phase 4 (approved)	CNR1
FLUTICASONE FUROATE	ChEMBL	Phase 4 (approved)	CNR1
GLIPIZIDE	ChEMBL	Phase 4 (approved)	CNR1
IMIPRAMINE	ChEMBL	Phase 4 (approved)	CNR1
INDOCYANINE GREEN ACID FORM	ChEMBL	Phase 4 (approved)	CNR1
KETOTIFEN	ChEMBL	Phase 4 (approved)	CNR1
LOFEPRAMINE	ChEMBL	Phase 4 (approved)	CNR1
LORCASERIN	ChEMBL	Phase 4 (approved)	CNR1
LOSARTAN	ChEMBL	Phase 4 (approved)	CNR1
MASOPROCOL	ChEMBL	Phase 4 (approved)	CNR1
MECLIZINE	ChEMBL	Phase 4 (approved)	CNR1
MEFLOQUINE	ChEMBL	Phase 4 (approved)	CNR1
MESTRANOL	ChEMBL	Phase 4 (approved)	CNR1
MIANSERIN	ChEMBL	Phase 4 (approved)	CNR1
MICONAZOLE	ChEMBL	Phase 4 (approved)	CNR1
MINAPRINE	ChEMBL	Phase 4 (approved)	CNR1
MITOTANE	ChEMBL	Phase 4 (approved)	CNR1
NAFTIFINE	ChEMBL	Phase 4 (approved)	CNR1
NEBIVOLOL	ChEMBL	Phase 4 (approved)	CNR1
NIMODIPINE	ChEMBL	Phase 4 (approved)	CNR1
NISOLDIPINE	ChEMBL	Phase 4 (approved)	CNR1
ORLISTAT	ChEMBL	Phase 4 (approved)	CNR1
PAROXETINE	ChEMBL	Phase 4 (approved)	CNR1
PERMETHRIN	ChEMBL	Phase 4 (approved)	CNR1
PILOCARPINE	ChEMBL	Phase 4 (approved)	CNR1
PRENYLAMINE	ChEMBL	Phase 4 (approved)	CNR1
PROCHLORPERAZINE	ChEMBL	Phase 4 (approved)	CNR1
PYRVINIUM	ChEMBL	Phase 4 (approved)	CNR1
RACECADOTRIL	ChEMBL	Phase 4 (approved)	CNR1
RALOXIFENE	ChEMBL	Phase 4 (approved)	CNR1
RIMEXOLONE	ChEMBL	Phase 4 (approved)	CNR1
ROSIGLITAZONE	ChEMBL	Phase 4 (approved)	CNR1
ROTIGOTINE	ChEMBL	Phase 4 (approved)	CNR1
SELEXIPAG	ChEMBL	Phase 4 (approved)	CNR1
SERTINDOLE	ChEMBL	Phase 4 (approved)	CNR1
TAMOXIFEN	ChEMBL	Phase 4 (approved)	CNR1
TEGASEROD	ChEMBL	Phase 4 (approved)	CNR1
TETRACAINE	ChEMBL	Phase 4 (approved)	CNR1
VENLAFAXINE	ChEMBL	Phase 4 (approved)	CNR1
ZAFIRLUKAST	ChEMBL	Phase 4 (approved)	CNR1
AMBROXOL	ChEMBL	Phase 3	CNR1
BENIDIPINE	ChEMBL	Phase 3	CNR1
CAMOSTAT	ChEMBL	Phase 3	CNR1
LERCANIDIPINE	ChEMBL	Phase 3	CNR1
MANIDIPINE 6300	ChEMBL	Phase 3	CNR1
NITRENDIPINE	ChEMBL	Phase 3	CNR1
OTILONIUM BROMIDE	ChEMBL	Phase 3	CNR1
BENZETHONIUM	ChEMBL	Phase 2	CNR1
CROCONAZOLE	ChEMBL	Phase 2	CNR1
DOMIPHEN	ChEMBL	Phase 2	CNR1
FLUNARIZINE	ChEMBL	Phase 2	CNR1