fluperamide

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| CAS_number = 53179-10-5

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| PubChem = 131534

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| ChemSpiderID = 116243

| UNII = 6H13T09362

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| ChEMBL = 421665

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| IUPAC_name = 4-[4-[4-chloro-3-(trifluoromethyl)phenyl]-4-hydroxypiperidin-1-yl]-N,N-dimethyl-2,2-diphenylbutanamide

| C=30 | H=32 | Cl=1 | F=3 | N=2 | O=2

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| SMILES = CN(C)C(=O)C(CCN1CCC(CC1)(C2=CC(=C(C=C2)Cl)C(F)(F)F)O)(C3=CC=CC=C3)C4=CC=CC=C4

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| StdInChI = 1S/C30H32ClF3N2O2/c1-35(2)27(37)29(22-9-5-3-6-10-22,23-11-7-4-8-12-23)17-20-36-18-15-28(38,16-19-36)24-13-14-26(31)25(21-24)30(32,33)34/h3-14,21,38H,15-20H2,1-2H3

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| StdInChIKey = WPYGCZCMGMVGNO-UHFFFAOYSA-N

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Fluperamide is a synthetic opioid structurally related to loperamide, developed as a potent antidiarrheal agent.{{cite journal | vauthors = Stokbroekx RA, Vandenberk J, Van Heertum AH, Van Laar GM, Van der Aa MJ, Van Bever WF, Janssen PA | title = Synthetic antidiarrheal agents. 2,2-Diphenyl-4-(4'-aryl-4'-hydroxypiperidino)butyramides | journal = Journal of Medicinal Chemistry | volume = 16 | issue = 7 | pages = 782–6 | date = July 1973 | pmid = 4725924 | doi = 10.1021/jm00265a009 | url = }}{{cite journal | vauthors = Chen Z, Davies E, Miller WS, Shan S, Valenzano KJ, Kyle DJ | title = Design and synthesis of 4-phenyl piperidine compounds targeting the mu receptor | journal = Bioorganic & Medicinal Chemistry Letters | volume = 14 | issue = 21 | pages = 5275–9 | date = November 2004 | pmid = 15454210 | doi = 10.1016/j.bmcl.2004.08.032 | url = }} Like loperamide, it acts primarily as a peripherally selective μ-opioid receptor agonist, effectively reducing gastrointestinal motility and fluid secretion without significant central nervous system effects due to limited blood-brain barrier penetration.

Fluperamide’s pharmacological profile was designed to maximize antidiarrheal efficacy while minimizing the risk of opioid-related side effects and abuse potential, a strategy that has contributed to the development of related compounds in the phenylpiperidine class. Although fluperamide demonstrated strong antidiarrheal activity in preclinical and early clinical studies, it was ultimately not commercialized, with loperamide becoming the preferred agent in this therapeutic category due to its favorable safety and efficacy.{{cite journal | vauthors = Baker DE | title = Loperamide: a pharmacological review | journal = Reviews in Gastroenterological Disorders | volume = 7 | issue = Suppl 3 | pages = S11–S18 | date = 2007 | pmid = 18192961 | doi = | url = }}