toloxatone

{{Short description|Antidepressant}}

{{Drugbox

| IUPAC_name = 5-(hydroxymethyl)-3-m-tolyloxazolidin-2-one

| image = Toloxatone.svg

| tradename =

| pregnancy_category =

| legal_status = Uncontrolled

| routes_of_administration = Oral

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 29218-27-7

| ATC_prefix = N06

| ATC_suffix = AG03

| PubChem = 34521

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| ChEBI = 134870

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 31769

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

| UNII = 5T206015T5

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D02559

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 18116

| C=11 | H=13 | N=1 | O=3

| smiles = O=C2OC(CO)CN2c1cccc(c1)C

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C11H13NO3/c1-8-3-2-4-9(5-8)12-6-10(7-13)15-11(12)14/h2-5,10,13H,6-7H2,1H3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = MXUNKHLAEDCYJL-UHFFFAOYSA-N

}}

Toloxatone (Humoryl) is an antidepressant launched in 1984 in France by Sanofi Aventis for the treatment of depression. It was discontinued in 2002.{{Cite web|url=https://sante.lefigaro.fr/medicaments/3215528-humoryl-200mg-gelule-30|title=Humoryl 200mg gelule 30}} It acts as a selective reversible inhibitor of MAO-A (RIMA).{{cite journal |vauthors=Berlin I, Zimmer R, Thiede HM, etal |title=Comparison of the monoamine oxidase inhibiting properties of two reversible and selective monoamine oxidase-A inhibitors moclobemide and toloxatone, and assessment of their effect on psychometric performance in healthy subjects |journal=British Journal of Clinical Pharmacology |volume=30 |issue=6 |pages=805–16 |date=December 1990 |pmid=1705137 |pmc=1368300 |doi= 10.1111/j.1365-2125.1990.tb05445.x}}

Synthesis

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The reaction between glycidol (1) and m-toluidine (2) gives 3-m-toluidinopropane-1,2-diol (3). Treatment with diethyl carbonate (4) in the presence of sodium methoxide leads to an intermolecular cycloaddition to give tomoxatone.Sungurbey, K .; Castaer, J .; Toloxatone. Drugs Fut 1976, 1, 12, 569.Douzon, C.; Fauvan, C.; Une nouvelle serie d'antidpresseurs: les derivs de l'hydroxymthyl-5-oxazolidinone-2. Chimie Thrapeutique 1973, 3, 324-327.DE2012120 Claude P Fauran, Guy M Raynaud, Rene A Oliver, Colette A Douzon, {{US patent|3655687}} (1972 to Delalande Sa).

See also

References

{{Reflist|2}}

{{Antidepressants}}

{{Anxiolytics}}

{{Monoamine metabolism modulators}}

Category:Reversible inhibitors of MAO-A

Category:Monoamine oxidase inhibitors

Category:2-Oxazolidinones

Category:Primary alcohols

Category:3-Tolyl compounds

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