Ibodutant

Ibodutant

Clinical data
Other names	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
Routes of administration	Oral
ATC code	none
Identifiers
IUPAC name Nα-[(1-{[(6-methyl-1-benzothien-2-yl)carbonyl]amino}cyclopentyl)carbonyl]-N-{[1-(tetrahydro-2H-pyran-4-ylmethyl)piperidin-4-yl]methyl}-D-phenylalaninamide
CAS Number	522664-63-7 Y
PubChem CID	11527495
IUPHAR/BPS	2117
ChemSpider	9702281 N
UNII	1H7RSQ28BJ
CompTox Dashboard (EPA)	DTXSID20966639
Chemical and physical data
Formula	C37H48N4O4S
Molar mass	644.88 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC1=CC2=C(C=C1)C=C(S2)C(=O)NC3(CCCC3)C(=O)NC(CC4=CC=CC=C4)C(=O)NCC5CCN(CC5)CC6CCOCC6
InChI 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 N Key:YQYSVMKCMIUCHY-WJOKGBTCSA-N N
NY (what is this?)  (verify)

Ibodutant was a candidate drug for irritable bowel syndrome diarrhea, developed by The Menarini Group. As of March 2015, it underwent a multicentre double blind efficacy clinical study. Ibodutant selectively blocks the tachykinin receptor NK₂, with blockade practically complete in nanomolar concentrations. A phase 2 trial in Europe (the IRIS-2 trial) completed in May 2012 with positive results. A 52-week phase 3 study was terminated as of 2015 because of low response and negative results of study NAK-06.

See also

• GR-159,897
• Nepadutant
• Saredutant

Further reading

• Spreitzer H (May 26, 2008). "Neue Wirkstoffe - Ibodutant". Österreichische Apothekerzeitung (in German) (11/2008): 541.
• Giuliani S, Altamura M, Maggi CA. "Ibodutant. Tachykinin NK₂ receptor antagonist, Treatment of irritable bowel syndrome". Drugs of the Future. 33 (2): 111–115. doi:10.1358/dof.2008.033.02.1181381.