Nufenoxole

Nufenoxole (SC-27166) is an antidiarrhoeal drug which acts as a peripherally selective opioid agonist, in a similar manner to loperamide and diphenoxylate. While it is able to activate μ-opioid receptors, it fails to cross the blood-brain barrier and so has a selective action against diarrhoea without producing analgesic effects.[1][2][3][4][5]

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
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC25H29N3O
Molar mass387.527 g·mol−1
3D model (JSmol)
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

See also

References
  1. US RE29556E, Adelstein GW, "1,1-Diaryl-1-oxadiazol-alkylamines", issued 28 February 1978, assigned to G.D. Searle & Company
  2. 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.
  3. 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.
  4. 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.
  5. 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.


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