Ibodutant

Ibodutant
Clinical data
Other names6-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
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC37H48N4O4S
Molar mass644.88 g·mol−1
3D model (JSmol)
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
 ☒NcheckY (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.[1]

See also

References

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

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.


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