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Fezolamine

Last updated: 2025-07-25 14:56:21

Fezolamine
Fezolamine
Clinical data
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • In general: uncontrolled
Identifiers
  • 3-(3,4-Diphenyl- 1H-pyrazol- 1-yl)- N,N-dimethylpropan- 1-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H23N3
Molar mass305.425 g·mol−1
3D model (JSmol)
  • n1c(c(cn1CCCN(C)C)c2ccccc2)c3ccccc3

Fezolamine (Win-41,528-2) is a drug which was investigated by Sterling Drug as an antidepressant in the 1980s.[1][2] The isomeric N,N-dimethyl-4,5-diphenyl-1H-pyrazole-1-propanamine was completely inactive in the primary antidepressant screens.

It acts as a serotonin, norepinephrine, and dopamine reuptake inhibitor, with 3- to 4-fold preference for the former neurotransmitter.[3] It was found to be effective and well tolerated in clinical trials but was never marketed.[4]

Changing the sidechain leads to an agent called ipazilide.

See also

References

  1. ↑ U.S. patent 4,182,895
  2. ↑ Bailey DM, Hansen PE, Hlavac AG, Baizman ER, Pearl J, DeFelice AF, Feigenson ME (February 1985). "3,4-Diphenyl-1H-pyrazole-1-propanamine antidepressants". Journal of Medicinal Chemistry. 28 (2): 256–60. doi:10.1021/jm00380a020. PMID 3968690.
  3. ↑ Baizman ER, Ezrin AM, Ferrari RA, Luttinger D (October 1987). "Pharmacologic profile of fezolamine fumarate: a nontricyclic antidepressant in animal models". The Journal of Pharmacology and Experimental Therapeutics. 243 (1): 40–54. PMID 3668867.
  4. ↑ Zisook S, Mendels J, Janowsky D, Feighner J, Lee JC, Fritz A (1987). "Efficacy and safety of fezolamine in depressed patients". Neuropsychobiology. 17 (3): 133–8. doi:10.1159/000118353. PMID 3683802.

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