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Fezolamine

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
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
PubChemCID
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 adrug which was investigated bySterling Drug as anantidepressant in the 1980s.[1][2] TheisomericN,N-dimethyl-4,5-diphenyl-1H-pyrazole-1-propanamine was completely inactive in the primary antidepressant screens.

It acts as aserotonin,norepinephrine, anddopaminereuptake inhibitor, with 3- to 4-fold preference for the formerneurotransmitter.[3] It was found to be effective and well tolerated inclinical trials but was never marketed.[4]

Changing the sidechain leads to an agent calledipazilide.

See also

[edit]

References

[edit]
  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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