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Asimadoline

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From Wikipedia, the free encyclopedia

Chemical compound

Pharmaceutical compound

Asimadoline
Clinical data

Other names	EMD-61753
ATC code	none
Identifiers
IUPAC name N-[(1S)-2-[(3S)-3-Hydroxypyrrolidin-1-yl]-1-phenylethyl]-N-methyl-2,2-diphenylacetamide
CAS Number	153205-46-0^N
PubChemCID	179340
ChemSpider	156107^Y
UNII	D0VK52NV5M
ChEMBL	ChEMBL1190199^N
CompTox Dashboard(EPA)	DTXSID60165285
Chemical and physical data
Formula	C₂₇H₃₀N₂O₂
Molar mass	414.549 g·mol⁻¹
3D model (JSmol)	Interactive image
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^Y Key:JHLHNYVMZCADTC-LOSJGSFVSA-N^Y
^NY (what is this?) (verify)

Asimadoline (EMD-61753) is an experimental drug which acts as a peripherally selectiveκ-opioid receptor (KOR)agonist.^[1]^[2] Because of its low penetration across theblood–brain barrier, asimadoline lacks thepsychotomimetic effects of centrally acting KOR agonists, and consequently was thought to have potential for medical use. It has been studied as a possible treatment forirritable bowel syndrome, with reasonable efficacy seen inclinical trials,^[3]^[4] but it has never been approved or marketed.

References

[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 & Motility.20 (9):971–9.doi:10.1111/j.1365-2982.2008.01183.x.PMC 2698012.PMID 18715494.
^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.S2CID 23570291.
^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.5 (11):1268–75.doi:10.1016/j.cgh.2007.07.011.PMC 2128734.PMID 17900994.

Drugs forfunctional gastrointestinal disorders (A03)

Drugs for
functional
bowel
disorders

Antimuscarinics

Tertiary amino group	Camylofin Dicycloverine Difemerine Dihexyverine Mebeverine Oxyphencyclimine Piperidolate Rociverine Trimebutine
Quaternary ammonium compounds	Benzilone Bevonium Diphemanil Fenpiverinium Glycopyrronium Hexocyclium Isopropamide Mepenzolate Methantheline Otilonium Oxyphenonium Penthienate Pipenzolate Poldine Prifinium Propantheline Tiemonium Timepidium Tridihexethyl