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 ;
PubChem CID	11527495;
IUPHAR/BPS	2117;
ChemSpider	9702281 ;
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 ; Key:YQYSVMKCMIUCHY-WJOKGBTCSA-N ;
	(what is this?) (verify)

Ibodutant was a candidate drug for irritable bowel syndrome diarrhea, developed by The Menarini Group. As of March 2015^[update], 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.^[1]

References

^ "Clinical Trials Database". Menarini Group. Retrieved 11 March 2015.

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.

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[1] "Clinical Trials Database". Menarini Group. Retrieved 11 March 2015.

[1]

Ibodutant

See also

References

Further reading

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)