Asimadoline

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Asimadoline
Asimadoline structure.png
Systematic (IUPAC) name
N-[(1S)-2-[(3S)-3-hydroxypyrrolidin-1-yl]-1-phenylethyl]-N-methyl-2,2-diphenylacetamide
Clinical data
Legal status
?
Identifiers
CAS number 153205-46-0 N
ATC code None
PubChem CID 179340
ChemSpider 156107 YesY
UNII D0VK52NV5M YesY
ChEMBL CHEMBL1190199 N
Chemical data
Formula C27H30N2O2 
Molecular mass 414.539 g/mol
 N (what is this?)  (verify)

Asimadoline (EMD-61753) is a drug which acts as a peripherally selective κ-opioid receptor (KOR) agonist.[1][2] Because of its poor ability to cross the blood–brain barrier, asimadoline lacks the psychotomimetic effects of centrally acting KOR 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]

Asimadoline.png

See also[edit]

References[edit]

  1. ^ Barber A, Gottschlich R; Gottschlich (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. 
  2. ^ 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. 
  3. ^ Delvaux M, Beck A, Jacob J, Bouzamondo H, Weber FT, Frexinos J; Beck; Jacob; Bouzamondo; Weber; Frexinos (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. 
  4. ^ Szarka LA, Camilleri M, Burton D, Fox JC, McKinzie S, Stanislav T, Simonson J, Sullivan N, Zinsmeister AR; Camilleri; Burton; Fox; McKinzie; Stanislav; Simonson; Sullivan; Zinsmeister (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.