TOLOXATONE

Details

Stereochemistry	RACEMIC
Molecular Formula	C11H13NO3
Molecular Weight	207.2258
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CC=CC(=C1)N2CC(CO)OC2=O

InChI

InChIKey=MXUNKHLAEDCYJL-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Description
Sources: https://www.drugbank.ca/drugs/DB09245 | https://www.ncbi.nlm.nih.gov/pubmed/1546124

Toloxatone is an antidepressant launched in 1984 in France for the treatment of depression. It is a selective reversible inhibitor of MAO-A (RIMA).

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Monoamine oxidase A 49 Target ID: CHEMBL1951 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28109809 \| https://www.ncbi.nlm.nih.gov/pubmed/24115740 \| https://www.ncbi.nlm.nih.gov/pubmed/24698	Inhibitor 8297		1.78 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Depression 235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1546124 https://www.ncbi.nlm.nih.gov/pubmed/3634492	Primary		Approved 8429	Humoryl Approved Use Humoryl is an antidepressant launched in 1984 in France for the treatment of depression.

PubMed

Title	Date	PubMed
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.	1990 Dec	1705137
The clinical pharmacology of depressive states.	2002 Mar	22034133
3-(1H-Pyrrol-1-yl)-2-oxazolidinones as reversible, highly potent, and selective inhibitors of monoamine oxidase type A.	2002 Mar 14	11881986
Highly efficient CuI-catalyzed coupling of aryl bromides with oxazolidinones using Buchwald's protocol: a short route to linezolid and toloxatone.	2003 Apr 3	12659549
Synthesis and biological evaluation of enantiomerically pure pyrrolyl-oxazolidinones as a new class of potent and selective monoamine oxidase type A inhibitors.	2003 Mar	12620419
A high-performance liquid chromatography method with photodiode-array UV detection for therapeutic drug monitoring of the nontricyclic antidepressant drugs.	2003 Oct	14508379
SL25.1131 [3(S),3a(S)-3-methoxymethyl-7-[4,4,4-trifluorobutoxy]-3,3a,4,5-tetrahydro-1,3-oxazolo[3,4-a]quinolin-1-one], a new, reversible, and mixed inhibitor of monoamine oxidase-A and monoamine oxidase-B: biochemical and behavioral profile.	2004 Sep	15178694
Neuroendocrine predictors of the evolution of depression.	2005	16156385
Design, synthesis, and biological activities of pyrrolylethanoneamine derivatives, a novel class of monoamine oxidases inhibitors.	2005 Jun 30	15974574
3-(1H-pyrrol-2-yl)-2-oxazolidinones as novel monoamine oxidase type A inhibitors.	2005 Mar	16787307
Quantification of tricyclic antidepressants and monoamine oxidase inhibitors by high-performance liquid chromatography-tandem mass spectrometry in whole blood.	2007 May	17555643
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.	2010 Dec	21818443
Analysis of activity and inhibition of oxygen-dependent enzymes by optical respirometry on the LightCycler system.	2010 Feb 15	19849999
Novel reversible monoamine oxidase A inhibitors: highly potent and selective 3-(1H-pyrrol-3-yl)-2-oxazolidinones.	2011 Dec 8	22017497

Patents

Sample Use Guides

In Vivo Use Guide

Adult : PO 200 mg 3 times/day.

Route of Administration: Oral

In Vitro Use Guide

The kinetics of MAO inhibition in vitro with rat brain stem (an area containing mostly type A MAO activity,) were measured with 14C-5-HT as substrate. MAO activity was non-competitively inhibited (maximal velocity was decreased by 80 %) by toloxatone (10uM), with apparent Ki value of 4.8 uM.

Name

Type

Language

TOLOXATONE

Official Name

English

TOLOXATONE [MART.]

Common Name

English

TOLOXATONE [MI]

Common Name

English

5-(HYDROXYMETHYL)-3-M-TOLYL-2-OXAZOLIDINONE

Systematic Name

English

HUMORYL

Brand Name

English

Toloxatone [WHO-DD]

Common Name

English

toloxatone [INN]

Common Name

English

(±)-5-(HYDROXYMETHYL)-3-M-TOLYL-2-OXAZOLIDINONE

Systematic Name

English

Classification Tree Code System Code

WHO-ATC

N06AG03