Asimadoline

Asimadoline
Systematic (IUPAC) name
	N-[(1S)-2-[(3S)-3-hydroxypyrrolidin-1-yl]-1-phenylethyl]-N-methyl-2,2-diphenylacetamide
Clinical data
Pregnancy cat.	?
Legal status	?
Identifiers
CAS number	153205-46-0
ATC code	?
PubChem	CID 179340
ChemSpider	156107
UNII	D0VK52NV5M
ChEMBL	CHEMBL1190199
Chemical data
Formula	C27H30N2O2
Mol. mass	414.539 g/mol
	SMILES CN([C@H](CN1CC[C@@H](C1)O)C2=CC=CC=C2)C(=O)C(C3=CC=CC=C3)C4=CC=CC=C4;
	InChI InChI=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 ; Key:JHLHNYVMZCADTC-LOSJGSFVSA-N ;
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Asimadoline (EMD-61753) is a drug which acts as a peripherally selective κ-opioid agonist.^[1]^[2] Because of its poor ability to cross the blood–brain barrier, asimadoline lacks the psychotomimetic effects of centrally acting kappa agonists, and consequently has more potential for medical use, and has been researched as a possible treatment for irritable bowel syndrome, with reasonable efficacy seen in clinical trials.^[3]^[4]

Synthesis [edit]

^ Barber A, Gottschlich R (October 1997). "Novel developments with selective, non-peptidic kappa-opioid receptor agonists". Expert Opinion on Investigational Drugs 6 (10): 1351–68. doi:10.1517/13543784.6.10.1351. PMID 15989506.
^ Camilleri M (September 2008). "Novel pharmacology: asimadoline, a [[kappa-opioid agonist]], and visceral sensation". Neurogastroenterology and Motility : the Official Journal of the European Gastrointestinal Motility Society 20 (9): 971–9. doi:10.1111/j.1365-2982.2008.01183.x. PMC 2698012. PMID 18715494. Wikilink embedded in URL title (help)
^ Delvaux M, Beck A, Jacob J, Bouzamondo H, Weber FT, Frexinos J (July 2004). "Effect of asimadoline, a kappa opioid agonist, on pain induced by colonic distension in patients with irritable bowel syndrome". Alimentary Pharmacology & Therapeutics 20 (2): 237–46. doi:10.1111/j.1365-2036.2004.01922.x. PMID 15233705.
^ Szarka LA, Camilleri M, Burton D, Fox JC, McKinzie S, Stanislav T, Simonson J, Sullivan N, Zinsmeister AR (November 2007). "Efficacy of on-demand asimadoline, a peripheral kappa-opioid agonist, in females with irritable bowel syndrome". Clinical Gastroenterology and Hepatology : the Official Clinical Practice Journal of the American Gastroenterological Association 5 (11): 1268–75. doi:10.1016/j.cgh.2007.07.011. PMC 2128734. PMID 17900994.