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Nufenoxole

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Chemical compound

Pharmaceutical compound

Nufenoxole
Identifiers

IUPAC name 2-[3-(2-azabicyclo[2.2.2]octan-2-yl)-1,1-diphenylpropyl]-5-methyl-1,3,4-oxadiazole
CAS Number	57726-65-5
PubChemCID	42551
ChemSpider	38808
UNII	39ER7N857V
KEGG	D05211
ChEMBL	ChEMBL3989894
CompTox Dashboard(EPA)	DTXSID80206427
Chemical and physical data
Formula	C₂₅H₂₉N₃O
Molar mass	387.527 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC1=NN=C(O1)C(CCN2CC3CCC2CC3)(C4=CC=CC=C4)C5=CC=CC=C5
InChI InChI=1S/C25H29N3O/c1-19-26-27-24(29-19)25(21-8-4-2-5-9-21,22-10-6-3-7-11-22)16-17-28-18-20-12-14-23(28)15-13-20/h2-11,20,23H,12-18H2,1H3 Key:CVOCKGAVXLCEGM-UHFFFAOYSA-N

Nufenoxole (SC-27166) is anantidiarrhoeal drug which acts as a peripherally selectiveopioid agonist, in a similar manner toloperamide. while it is able to activateμ-opioid receptors, it fails to cross theblood–brain barrier and so has a selective action against diarrhoea without producinganalgesic effects.^[1]^[2]^[3]^[4]^[5]

^US RE29556E, Adelstein GW, "1,1-Diaryl-1-oxadiazol-alkylamines", issued 28 February 1978, assigned to G.D. Searle & Company
^Dajani EZ, Bianchi RG, East PF, Bloss JL, Adelstein GW, Yen CH (December 1977). "The pharmacology of SC-27166: a novel antidiarrheal agent".The Journal of Pharmacology and Experimental Therapeutics.203 (3):512–26.PMID 411912.
^Mackerer CR, Brougham LR, East PF, Bloss JL, Dajani EZ, Clay GA (December 1977). "Antidiarrheal and central nervous system activities of SC-27166 (2-[3 - 5 - methyl - 1, 3, 4 - oxadiazol - 2 - yl) - 3, 3 - diphenylpropyl] - 2 - azabicyclo [2.2.2]octane), a new antidiarrheal agent, resulting from binding to opiate receptor sites of brain and myenteric plexus".The Journal of Pharmacology and Experimental Therapeutics.203 (3):527–38.PMID 200732.
^Niemegeers CJ, McGuire JL, Heykants JJ, Janssen PA (September 1979). "Dissociation between opiate-like and antidiarrheal activities of antidiarrheal drugs".The Journal of Pharmacology and Experimental Therapeutics.210 (3):327–33.PMID 480185.
^Korey A, Zilm DH, Sellers EM (May 1980). "Dependence liability of two antidiarrheals, nufenoxole and loperamide".Clinical Pharmacology and Therapeutics.27 (5):659–64.doi:10.1038/clpt.1980.93.PMID 7371363.S2CID 35222789.