fezolamine

{{Short description|Chemical compound}}

{{Drugbox

| IUPAC_name = 3-(3,4-Diphenyl- 1H-pyrazol- 1-yl)- N,N-dimethylpropan- 1-amine

| image = Fezolamine Structure.svg

| image_class = skin-invert-image

| tradename =

| pregnancy_category =

| legal_status = Uncontrolled

| routes_of_administration = Oral

| bioavailability =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number = 80410-36-2

| ATC_prefix = none

| ATC_suffix =

| PubChem = 54567

| ChemSpiderID = 49284

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 1133E05F6C

| C=20 | H=23 | N=3

| smiles = 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.{{US Patent|4182895}}{{cite journal | vauthors = Bailey DM, Hansen PE, Hlavac AG, Baizman ER, Pearl J, DeFelice AF, Feigenson ME | title = 3,4-Diphenyl-1H-pyrazole-1-propanamine antidepressants | journal = Journal of Medicinal Chemistry | volume = 28 | issue = 2 | pages = 256–60 | date = February 1985 | pmid = 3968690 | doi = 10.1021/jm00380a020 }} 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.{{cite journal | vauthors = Baizman ER, Ezrin AM, Ferrari RA, Luttinger D | title = Pharmacologic profile of fezolamine fumarate: a nontricyclic antidepressant in animal models | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 243 | issue = 1 | pages = 40–54 | date = October 1987 | pmid = 3668867 }} It was found to be effective and well tolerated in clinical trials but was never marketed.{{cite journal | vauthors = Zisook S, Mendels J, Janowsky D, Feighner J, Lee JC, Fritz A | title = Efficacy and safety of fezolamine in depressed patients | journal = Neuropsychobiology | volume = 17 | issue = 3 | pages = 133–8 | year = 1987 | pmid = 3683802 | doi = 10.1159/000118353 }}

Changing the sidechain leads to an agent called [https://pubchem.ncbi.nlm.nih.gov/compound/60650 ipazilide].