Ibodutant: Difference between revisions

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 444434892

| IUPAC_name = ''N''α-[(1-<nowiki/>{[(6-methyl-1-benzothien-2-yl)carbonyl]amino}cyclopentyl)carbonyl]-''N''-<nowiki/>{[1-(tetrahydro-2''H''-pyran-4-ylmethyl)piperidin-4-yl]methyl}-<small>D</small>-phenylalaninamide

| image = Ibodutant_structure.svg

| width = 150px

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| routes_of_administration = Oral

<!--Pharmacokinetic data-->

| bioavailability =

| protein_bound =

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<!--Identifiers-->

| IUPHAR_ligand = 2117

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 522664-63-7

| ATC_prefix = none

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| ATC_supplemental =

| PubChem = 11527495

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 9702281

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = YQYSVMKCMIUCHY-WJOKGBTCSA-N

<!--Chemical data-->

| chemical_formula =

| C=37 | H=48 | N=4 | O=4 | S=1

| 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

| synonyms = 6-methyl-''N''-[1-[{{bracket|(2''R'')-1-[{{bracket|1-(oxan-4-ylmethyl)piperidin-4- yl}}methylamino]-1-oxo-3-phenylpropan-2-yl}}carbamoyl]cyclopentyl]-1-benzothiophene-2-carboxamide

'''Ibodutant''' was a candidate drug for [[irritable bowel syndrome]] diarrhea, developed by The [[Menarini]] Group. {{As of|2015|March}}, it underwent a multicentre double blind efficacy clinical [[Clinical trial|study]]. Ibodutant selectively blocks the [[tachykinin receptor]] [[NK2 receptor|NK₂]], with blockade practically complete in nano[[molar concentration|molar]] 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.<ref>{{Cite web|url = http://www.menarini.com/Home/Innovation-Research/Clinical-studies/Clinical-Trials-Database|title = Clinical Trials Database|access-date = 11 March 2015|publisher = Menarini Group}}</ref>

==See also==

* [[GR-159,897]]

* [[Nepadutant]]

* [[Saredutant]]

==References==

{{Reflist}}

== Further reading ==

{{refbegin}}

* {{cite journal | vauthors = Spreitzer H | date = May 26, 2008 | title = Neue Wirkstoffe - Ibodutant | journal = Österreichische Apothekerzeitung | issue = 11/2008 | pages = 541 | language = de}}

* {{cite journal | vauthors = Giuliani S, Altamura M, Maggi CA | title = Ibodutant. Tachykinin NK₂ receptor antagonist, Treatment of irritable bowel syndrome. | journal = Drugs of the Future | volume = 33 | issue = 2 | pages = 111–115| doi = 10.1358/dof.2008.033.02.1181381 }}

{{refend}}

{{Neurokinin receptor modulators}}

[[Category:Carboxamides]]

[[Category:Tetrahydropyrans]]

[[Category:Cyclopentanes]]

{{nervous-system-drug-stub}}