Asimadoline

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 ;
PubChem CID	179340;
ChemSpider	156107 ;
UNII	D0VK52NV5M;
ChEMBL	ChEMBL1190199 ;
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 ; Key:JHLHNYVMZCADTC-LOSJGSFVSA-N ;
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Asimadoline (EMD-61753) is an experimental drug which acts as a peripherally selective κ-opioid receptor (KOR) agonist.^[1]^[2] 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,^[3]^[4] but it has never been approved or marketed.

^ 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.

[pmid15989506-1] 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.

[pmid18715494-2] 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.

[pmid15233705-3] 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.

[pmid17900994-4] 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.

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