From Wikipedia, the free encyclopedia
Chemical compound
Asimadoline
Other names EMD-61753
ATC code
N -[(1S )-2-[(3S )-3-Hydroxypyrrolidin-1-yl]-1-phenylethyl]-N -methyl-2,2-diphenylacetamide
CAS Number
PubChem
CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (
EPA )
Formula C 27 H 30 N 2 O 2
Molar mass 414.549 g·mol−1 3D model (
JSmol )
CN([C@H](CN1CC[C@@H](C1)O)C2=CC=CC=C2)C(=O)C(C3=CC=CC=C3)C4=CC=CC=C4
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
N Y
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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.
See also
References
^ 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 .