Fezolamine

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.

Fezolamine

Clinical data
Routes of administration	Oral
ATC code	none
Legal status
Legal status	In general: uncontrolled
Identifiers
IUPAC name 3-(3,4-Diphenyl- 1H-pyrazol- 1-yl)- N,N-dimethylpropan- 1-amine
CAS Number	80410-36-2
PubChem CID	54567
ChemSpider	49284
UNII	1133E05F6C
CompTox Dashboard (EPA)	DTXSID00230305
Chemical and physical data
Formula	C20H23N3
Molar mass	305.425 g·mol−1
3D model (JSmol)	Interactive image
SMILES n1c(c(cn1CCCN(C)C)c2ccccc2)c3ccccc3

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]

See also

• 3,3-Diphenylcyclobutanamine

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.