Toloxatone
Antidepressant
- N06AG03 (WHO)
- In general: uncontrolled
- 5-(hydroxymethyl)-3-m-tolyloxazolidin-2-one
- 29218-27-7
Y
- 34521
- 31769
Y
- 5T206015T5
- D02559
Y
- CHEBI:134870
- ChEMBL18116
Y
- DTXSID40865478
![Edit this at Wikidata](http://upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png)
- Interactive image
- O=C2OC(CO)CN2c1cccc(c1)C
InChI
- InChI=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
Y
- Key:MXUNKHLAEDCYJL-UHFFFAOYSA-N
Y
Toloxatone (Humoryl) is an antidepressant launched in 1984 in France by Sanofi Aventis for the treatment of depression. It was discontinued in 2002.[1] It acts as a selective reversible inhibitor of MAO-A (RIMA).[2]
Synthesis
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.[3][4][5]
See also
References
- ^ "Humoryl 200mg gelule 30".
- ^ Berlin I, Zimmer R, Thiede HM, et al. (December 1990). "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". British Journal of Clinical Pharmacology. 30 (6): 805–16. doi:10.1111/j.1365-2125.1990.tb05445.x. PMC 1368300. PMID 1705137.
- ^ 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, U.S. patent 3,655,687 (1972 to Delalande Sa).
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Miscellaneous | |
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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