nepadutant

{{Short description|Chemical compound}}

{{Drugbox

| IUPAC_name = (2S)-2-[[(3S,6S,9S,12S)-12-[[(2S)-4-[[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]amino]-2-amino-4-oxobutanoyl]amino]-6-benzyl-9-(1H-indol-3-ylmethyl)-5,8,11,14-tetraoxo-1,4,7,10-tetrazacyclotetradecane-3-carbonyl]amino]-4-methylpentanoic acid

| image = Nepadutant.svg

| width = 250

| CAS_number = 183747-35-5

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = XW59TYL1XH

| ATC_prefix = None

| ATC_suffix =

| PubChem = 3086682

| DrugBank =

| IUPHAR_ligand = 2123

| ChemSpiderID = 2343247

| C=45 | H=60 | N=10 | O=14

| SMILES = CC(C)C[C@@H](C(=O)O)NC(=O)[C@@H]1CNC(=O)C[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)Cc2ccccc2)Cc3c[nH]c4c3cccc4)NC(=O)[C@H](CC(=O)N[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)NC(=O)C)N

| StdInChI = 1S/C45H60N10O14/c1-21(2)13-31(45(67)68)53-43(66)32-19-48-34(58)17-30(50-39(62)26(46)16-35(59)55-44-36(49-22(3)57)38(61)37(60)33(20-56)69-44)42(65)52-29(15-24-18-47-27-12-8-7-11-25(24)27)41(64)51-28(40(63)54-32)14-23-9-5-4-6-10-23/h4-12,18,21,26,28-33,36-38,44,47,56,60-61H,13-17,19-20,46H2,1-3H3,(H,48,58)(H,49,57)(H,50,62)(H,51,64)(H,52,65)(H,53,66)(H,54,63)(H,55,59)(H,67,68)/t26-,28-,29-,30-,31-,32-,33+,36+,37+,38+,44+/m0/s1

| StdInChIKey = NPSVXOVMLVOMDD-SXRVEDALSA-N

| bioavailability = <3% (oral){{cite book|title=Annual Reports in Medicinal Chemistry|url=https://books.google.com/books?id=pJ1TIGO9VVYC&pg=PA56|date=8 September 1999|publisher=Academic Press|isbn=978-0-08-058378-5|pages=56–}}

| protein_bound =

| metabolism =

| elimination_half-life = 44 minutes (IV)

| excretion =

| pregnancy_AU =

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| routes_of_administration = Injection{{cite book| vauthors = Holzer P |title=Tachykinins|url=https://books.google.com/books?id=Fo4bKOwXbgsC&pg=PA224|date=17 June 2004|publisher=Springer|isbn=978-3-540-20690-3|pages=224–226}}

}}

Nepadutant (INN) (code name MEN-11420) is a glycosylated bicyclic cyclohexapeptide drug which acts as a highly selective NK₂ receptor antagonist.{{cite book| vauthors = Regitz-Zagrosek V |title=Sex and Gender Differences in Pharmacology|url=https://books.google.com/books?id=-r02bdyoSEgC&pg=PA489|date=2 October 2012|publisher=Springer Science & Business Media|isbn=978-3-642-30726-3|pages=489–}}{{cite book|author=Royal Society of Chemistry (Great Britain)|title=Amino Acids, Peptides and Proteins|url=https://books.google.com/books?id=WcMdAQAAMAAJ|date=January 2003|publisher=Royal Society of Chemistry|isbn=978-0-85404-242-5}} It was developed by the Menarini Group and investigated for the treatment of functional gastrointestinal disorders and asthma but was never marketed.{{cite book| vauthors = Frank B |title=Women's Issues in Gastroenterology, An Issue of Gastroenterology Clinics|url=https://books.google.com/books?id=1naXWRfNZIMC&pg=PT54|date=29 June 2011|publisher=Elsevier Health Sciences|isbn=978-1-4557-1220-5|pages=54–55}}{{cite book| vauthors = Jancso G |title=Neurogenic Inflammation in Health and Disease|url=https://books.google.com/books?id=yvsEGxG5gNcC&pg=PA297|date=27 November 2008|publisher=Elsevier|isbn=978-0-444-53229-9|pages=297–}}