Ibodutant

Summary

Ibodutant (CHEMBL266125) is a phase-3 clinical-stage small molecule targeting TACR2; indicated across 1 condition including irritable bowel syndrome.

At a glance

• Status: Max clinical phase 3 (not approved)
• Modality: Small molecule
• Targets: 1 (TACR2)
• Indications: 1 condition
• Clinical trials: 5
• Chemistry: 644.9 Da · C37H48N4O4S

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL266125
Name	Ibodutant
Type	Small molecule
Max phase	3
FDA approved	no
PubChem CID	11527495
Molecular formula	C37H48N4O4S
Molecular weight	644.9
InChIKey	YQYSVMKCMIUCHY-WJOKGBTCSA-N

SMILES: CC1=CC2=C(C=C1)C=C(S2)C(=O)NC3(CCCC3)C(=O)N[C@H](CC4=CC=CC=C4)C(=O)NCC5CCN(CC5)CC6CCOCC6

IUPAC name: 6-methyl-N-[1-[[(2R)-1-[[1-(oxan-4-ylmethyl)piperidin-4-yl]methylamino]-1-oxo-3-phenylpropan-2-yl]carbamoyl]cyclopentyl]-1-benzothiophene-2-carboxamide

Also known as: Ibodutant, Men15596, IBODUTANT

Patent coverage: 61 distinct patent families (126 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 121 (96%) 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
TACR2	NK2 receptor	Antagonist	10.3	0.2%	P21452

Broader ChEMBL bioactivity targets: 1 (assay-derived). Sample: Substance-K receptor.

Bioactivity

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

Target	pChembl	Type	Value	Unit	Activity ID
TACR2	10.12	Ki	0.08	nM	CHEMBL_ACT_1924309

Target pathways

Aggregated over 1 target gene(s): TACR2.

Top Reactome pathways

2 total, by targets touching each:

Pathway	Targets	Genes
Tachykinin receptors bind tachykinins	1	TACR2
G alpha (q) signalling events	1	TACR2

Dominant GO biological processes

GO term	Targets
muscle contraction	1
adenylate cyclase-activating G protein-coupled receptor signaling pathway	1
phospholipase C-activating tachykinin receptor signaling pathway	1
tachykinin receptor signaling pathway	1
positive regulation of acetylcholine secretion, neurotransmission	1
intestine smooth muscle contraction	1
negative regulation of luteinizing hormone secretion	1
operant conditioning	1
positive regulation of vascular permeability	1
positive regulation of monoatomic ion transport	1
positive regulation of smooth muscle contraction	1
response to electrical stimulus	1
prolactin secretion	1
positive regulation of uterine smooth muscle contraction	1
positive regulation of flagellated sperm motility	1

Indications & clinical

Indications

1 indication (0 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).

Indication	Trial phase	MONDO	EFO
irritable bowel syndrome	3	MONDO:0005052	EFO:0000555

Clinical trials

Total trials: 5.

Phase distribution

Phase	Trials
PHASE3	3
PHASE2	2

Top trials by phase / activity

NCT	Phase	Status	Title
NCT02107196	PHASE3	COMPLETED	12-Week Efficacy and Safety Study of Ibodutant in Women With Irritable Bowel Syndrome With Diarrhea (IBS-D)
NCT02120027	PHASE3	TERMINATED	52-Week Efficacy and Safety Study of Ibodutant in Women With Irritable Bowel Syndrome With Diarrhea (IBS-D)
NCT02320318	PHASE3	WITHDRAWN	12-Week Efficacy and Safety Study of Ibodutant in Women With Irritable Bowel Syndrome With Diarrhea (IBS-D)
NCT00761007	PHASE2	COMPLETED	Ibodutant for Relief of Irritable Bowel Syndrome (IRIS)
NCT01303224	PHASE2	COMPLETED	Ibodutant for Relief of Irritable Bowel Syndrome With Diarrhoea (IBS-D)

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.

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

Molecule	Source	Status	Shared targets
AMIODARONE	ChEMBL	Phase 4 (approved)	TACR2
ASTEMIZOLE	ChEMBL	Phase 4 (approved)	TACR2
BITHIONOL	ChEMBL	Phase 4 (approved)	TACR2
CHLORPROMAZINE	ChEMBL	Phase 4 (approved)	TACR2
CLOTRIMAZOLE	ChEMBL	Phase 4 (approved)	TACR2
CYCLOSPORINE	ChEMBL	Phase 4 (approved)	TACR2
DANAZOL	ChEMBL	Phase 4 (approved)	TACR2
DIETHYLSTILBESTROL	ChEMBL	Phase 4 (approved)	TACR2
DOCETAXEL	ChEMBL	Phase 4 (approved)	TACR2
EBASTINE	ChEMBL	Phase 4 (approved)	TACR2
ECONAZOLE	ChEMBL	Phase 4 (approved)	TACR2
FLUPHENAZINE	ChEMBL	Phase 4 (approved)	TACR2
GENTIAN VIOLET	ChEMBL	Phase 4 (approved)	TACR2
GRAMICIDIN	ChEMBL	Phase 4 (approved)	TACR2
HALOPROGIN	ChEMBL	Phase 4 (approved)	TACR2
HEXACHLOROPHENE	ChEMBL	Phase 4 (approved)	TACR2
KETOCONAZOLE	ChEMBL	Phase 4 (approved)	TACR2
LOVASTATIN	ChEMBL	Phase 4 (approved)	TACR2
MICONAZOLE	ChEMBL	Phase 4 (approved)	TACR2
MONTELUKAST	ChEMBL	Phase 4 (approved)	TACR2
NELFINAVIR	ChEMBL	Phase 4 (approved)	TACR2
OXICONAZOLE	ChEMBL	Phase 4 (approved)	TACR2
PACLITAXEL	ChEMBL	Phase 4 (approved)	TACR2
PASIREOTIDE	ChEMBL	Phase 4 (approved)	TACR2
RALOXIFENE	ChEMBL	Phase 4 (approved)	TACR2
RITONAVIR	ChEMBL	Phase 4 (approved)	TACR2
SAQUINAVIR	ChEMBL	Phase 4 (approved)	TACR2
SULCONAZOLE	ChEMBL	Phase 4 (approved)	TACR2
SULOCTIDIL	ChEMBL	Phase 4 (approved)	TACR2
TAMOXIFEN	ChEMBL	Phase 4 (approved)	TACR2
TERFENADINE	ChEMBL	Phase 4 (approved)	TACR2
VINORELBINE	ChEMBL	Phase 4 (approved)	TACR2
ENCLOMIPHENE	ChEMBL	Phase 3	TACR2
INDINAVIR	ChEMBL	Phase 3	TACR2
PEXACERFONT	ChEMBL	Phase 3	TACR2
SAREDUTANT	ChEMBL	Phase 3	TACR2
SERLOPITANT	ChEMBL	Phase 3	TACR2
AZD-7624	ChEMBL	Phase 2	TACR2
BENZETHONIUM CHLORIDE	ChEMBL	Phase 2	TACR2
CIGLITAZONE	ChEMBL	Phase 2	TACR2
DARIGABAT	ChEMBL	Phase 2	TACR2
DNK333	ChEMBL	Phase 2	TACR2
METERGOLINE	ChEMBL	Phase 2	TACR2
OSANETANT	ChEMBL	Phase 2	TACR2
TALNETANT	ChEMBL	Phase 2	TACR2
Amiloride	PubChem	Approved	TACR2
Amoxapine	PubChem	Approved	TACR2
Amoxicillin	PubChem	Approved	TACR2
Baclofen	PubChem	Approved	TACR2
Bumetanide	PubChem	Approved	TACR2
Caffeine	PubChem	Approved	TACR2
Candesartan	PubChem	Approved	TACR2
Candesartan Cilexetil	PubChem	Approved	TACR2
Celecoxib	PubChem	Approved	TACR2
chlorpheniramine	PubChem	Approved	TACR2
Diclofenac	PubChem	Approved	TACR2
Diphenhydramine	PubChem	Approved	TACR2
Doxepin	PubChem	Approved	TACR2
Dyclonine	PubChem	Approved	TACR2
Fluoxetine	PubChem	Approved	TACR2