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^Y
ATC code	?
PubChem	CID 179340
ChemSpider	156107^Y
UNII	D0VK52NV5M^Y
ChEMBL	CHEMBL1190199^Y
Chemical data
Formula	C₂₇H₃₀N₂O₂
Mol. mass	414.539 g/mol
SMILES	eMolecules & PubChem
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
Y(what is this?) (verify)

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

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 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. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2698012.
^ 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. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2128734.

Drugs for functional gastrointestinal disorders (A03)

Drugs for
functional bowel disorders

Antimuscarinics

Tertiary amino group	Oxyphencyclimine • Camylofin • Mebeverine • Trimebutine • Rociverine • Dicycloverine • Dihexyverine • Difemerine • Piperidolate

Quaternary ammonium compounds	Benzilone • Mepenzolate • Pipenzolate • Glycopyrronium • Oxyphenonium • Penthienate • Methantheline • Propantheline • Otilonium bromide • Tridihexethyl • Isopropamide • Hexocyclium • Poldine • Bevonium • Diphemanil • Tiemonium iodide • Prifinium bromide • Timepidium bromide • Fenpiverinium

Phosphodiesterase inhibitors

Papaverine • Drotaverine • Moxaverine

Acting on serotonin receptors

5-HT₃ antagonists (Alosetron, Cilansetron) • 5-HT₄ agonists (Mosapride, Prucalopride, Tegaserod)

Other

Alverine • Caroverine • Chlorbenzoxamine • Diisopromine • Dimethylaminopropionylphenothiazine • Fenpiprane • Fenoverine • Idanpramine • Isometheptene • Phloroglucinol • Pinaverium • Proxazole • Silicones • Tiropramide • Trepibutone • Trimethyldiphenylpropylamine

Belladonna and derivatives
(antimuscarinics)

tertiary amines: Atropine • Hyoscyamine

quaternary ammonium compounds: Scopolamine (Butylscopolamine, Methylscopolamine) • Methylatropine • Fentonium • Cimetropium bromide

Propulsives

primarily dopamine antagonists (Metoclopramide/Bromopride, Clebopride, Domperidone, Alizapride) • 5-HT₄ agonists (Cinitapride • Cisapride)

M: DIG

anat(t, g, p)/phys/devp/enzy

noco/cong/tumr, sysi/epon

proc, drug(A2A/2B/3/4/5/6/7/14/16), blte