asimadoline

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477350817

| IUPAC_name = N-[(1S)-2-[(3S)-3-Hydroxypyrrolidin-1-yl]-1-phenylethyl]-N-methyl-2,2-diphenylacetamide

| synonyms=EMD-61753

| image = Asimadoline Structure.svg

| image_class = skin-invert-image

| width = 240

| tradename =

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| routes_of_administration =

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| protein_bound =

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| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 153205-46-0

| ATC_prefix = none

| ATC_suffix =

| PubChem = 179340

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

| DrugBank =

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

| UNII = D0VK52NV5M

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 1190199

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 156107

| smiles = CN([C@H](CN1CC[C@@H](C1)O)C2=CC=CC=C2)C(=O)C(C3=CC=CC=C3)C4=CC=CC=C4

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C27H30N2O2/c1-28(25(21-11-5-2-6-12-21)20-29-18-17-24(30)19-29)27(31)26(22-13-7-3-8-14-22)23-15-9-4-10-16-23/h2-16,24-26,30H,17-20H2,1H3/t24-,25+/m0/s1

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = JHLHNYVMZCADTC-LOSJGSFVSA-N

| C=27 | H=30 | N=2 | O=2

}}

Asimadoline (EMD-61753) is an experimental drug which acts as a peripherally selective κ-opioid receptor (KOR) agonist.{{cite journal | vauthors =Barber A, Gottschlich R |title=Novel developments with selective, non-peptidic kappa-opioid receptor agonists |journal=Expert Opinion on Investigational Drugs |volume=6 |issue=10 |pages=1351–68 |date=October 1997 |pmid=15989506 |doi=10.1517/13543784.6.10.1351 }}{{cite journal |author=Camilleri M |title=Novel pharmacology: asimadoline, a kappa-opioid agonist, and visceral sensation |journal=Neurogastroenterology & Motility |volume=20 |issue=9 |pages=971–9 |date=September 2008 |pmid=18715494 |pmc=2698012 |doi=10.1111/j.1365-2982.2008.01183.x }} Because of its low penetration across the blood–brain barrier, asimadoline lacks the psychotomimetic effects of centrally acting KOR agonists, and consequently was thought to have potential for medical use. It has been studied as a possible treatment for irritable bowel syndrome, with reasonable efficacy seen in clinical trials,{{cite journal |vauthors=Delvaux M, Beck A, Jacob J, Bouzamondo H, Weber FT, Frexinos J |title=Effect of asimadoline, a kappa opioid agonist, on pain induced by colonic distension in patients with irritable bowel syndrome |journal=Alimentary Pharmacology & Therapeutics |volume=20 |issue=2 |pages=237–46 |date=July 2004 |pmid=15233705 |doi=10.1111/j.1365-2036.2004.01922.x |s2cid=23570291 |doi-access=free }}{{cite journal |vauthors=Szarka LA, Camilleri M, Burton D, Fox JC, McKinzie S, Stanislav T, Simonson J, Sullivan N, Zinsmeister AR |title=Efficacy of on-demand asimadoline, a peripheral kappa-opioid agonist, in females with irritable bowel syndrome |journal=Clinical Gastroenterology and Hepatology |volume=5 |issue=11 |pages=1268–75 |date=November 2007 |pmid=17900994 |pmc=2128734 |doi=10.1016/j.cgh.2007.07.011 }} but it has never been approved or marketed.