IBODUTANT

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C37H48N4O4S
Molecular Weight	644.866
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CC=C2C=C(SC2=C1)C(=O)NC3(CCCC3)C(=O)N[C@H](CC4=CC=CC=C4)C(=O)NCC5CCN(CC6CCOCC6)CC5

InChI

InChIKey=YQYSVMKCMIUCHY-WJOKGBTCSA-N

InChI=1S/C37H48N4O4S/c1-26-9-10-30-23-33(46-32(30)21-26)35(43)40-37(15-5-6-16-37)36(44)39-31(22-27-7-3-2-4-8-27)34(42)38-24-28-11-17-41(18-12-28)25-29-13-19-45-20-14-29/h2-4,7-10,21,23,28-29,31H,5-6,11-20,22,24-25H2,1H3,(H,38,42)(H,39,44)(H,40,43)/t31-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C37H48N4O4S
Molecular Weight	644.866
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://clinicaltrials.gov/ct2/show/NCT02120027 | https://www.ncbi.nlm.nih.gov/pubmed/19218528

Menarini was developing ibodutant (also known as MEN15596) as a selective neurokinin (NK) 2 and tachykinin receptor antagonist. It is known that tachykinins have been implicated in the pathophysiology of irritable bowel syndrome (IBS) with diarrhoea. Ibodutant was studied as a treatment for gastrointestinal disorders. A phase 2 trial completed in May 2012 with positive results. Ibodutant participated in a 52-week phase 3 in women with IBS with diarrhea, however, the study was terminated because of the negative results of the sister study NAK-06 and the low overall response rate at week 24.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Substance-K receptor 1 Target ID: P21452 Gene ID: 6865.0 Gene Symbol: TACR2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/19218528	Antagonist 2778

PubMed

Title	Date	PubMed
MEN15596, a novel nonpeptide tachykinin NK2 receptor antagonist.	2006 Nov 7	16979621
Multifaceted approach to determine the antagonist molecular mechanism and interaction of ibodutant ([1-(2-phenyl-1R-[[1-(tetrahydropyran-4-ylmethyl)-piperidin-4-ylmethyl]-carbamoyl]-ethylcarbamoyl)-cyclopentyl]-amide) at the human tachykinin NK2 receptor.	2009 May	19218528
The neurokinin-2 receptor antagonist ibodutant improves overall symptoms, abdominal pain and stool pattern in female patients in a phase II study of diarrhoea-predominant IBS.	2017 Aug	27196574
The place of tachykinin NK2 receptor antagonists in the treatment diarrhea-predominant irritable bowel syndrome.	2019 Feb	31019119

Patents

Sample Use Guides

In Vivo Use Guide

Ibodutant 10 mg

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:30:04 UTC 2023` Edited by `admin` on `Fri Dec 15 18:30:04 UTC 2023`
Record UNII	1H7RSQ28BJ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

IBODUTANT

Official Name

English

Ibodutant [WHO-DD]

Common Name

English

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

Systematic Name

English

ibodutant [INN]

Common Name

English

Code System Code Type Description

CAS

522664-63-7