Fezolamine

Fezolamine
Clinical data
Routes of
administration		Oral
Drug classSerotonin-norepinephrine-dopamine reuptake inhibitor; Antidepressant
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. 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. It was found to be effective and well tolerated in clinical trials but was never marketed.

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.