TOLOXATONE

Possibly Marketed Outside US

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 52 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 8504		1.78 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Depression 240 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1546124 https://www.ncbi.nlm.nih.gov/pubmed/3634492	Primary		Approved 8583	Humoryl Approved Use Humoryl is an antidepressant launched in 1984 in France for the treatment of depression.

Doses

Dose	Population	Adverse events
1 g single, intravenous Dose: 1 g Route: intravenous Route: single Dose: 1 g Sources: https://pubmed.ncbi.nlm.nih.gov/7200786/	healthy Health Status: healthy Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7200786/	Sources: https://pubmed.ncbi.nlm.nih.gov/7200786/
2 g single, oral Dose: 2 g Route: oral Route: single Dose: 2 g Sources: https://pubmed.ncbi.nlm.nih.gov/2353326/	unknown Health Status: unknown Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/2353326/	Other AEs: Drowsiness, Adrenergic syndrome... Other AEs: Drowsiness Adrenergic syndrome (mild) Sources: https://pubmed.ncbi.nlm.nih.gov/2353326/

AEs

AE	Significance	Dose	Population
Drowsiness		2 g single, oral Dose: 2 g Route: oral Route: single Dose: 2 g Sources: https://pubmed.ncbi.nlm.nih.gov/2353326/	unknown Health Status: unknown Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/2353326/
Adrenergic syndrome	mild	2 g single, oral Dose: 2 g Route: oral Route: single Dose: 2 g Sources: https://pubmed.ncbi.nlm.nih.gov/2353326/	unknown Health Status: unknown Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/2353326/

PubMed

Title	Date	PubMed
Novel reversible monoamine oxidase A inhibitors: highly potent and selective 3-(1H-pyrrol-3-yl)-2-oxazolidinones.	2011-12-08	22017497
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.	2010-12	21818443
Analysis of activity and inhibition of oxygen-dependent enzymes by optical respirometry on the LightCycler system.	2010-02-15	19849999
Quantification of tricyclic antidepressants and monoamine oxidase inhibitors by high-performance liquid chromatography-tandem mass spectrometry in whole blood.	2007-05	17555643
Design, synthesis, and biological activities of pyrrolylethanoneamine derivatives, a novel class of monoamine oxidases inhibitors.	2005-06-30	15974574
3-(1H-pyrrol-2-yl)-2-oxazolidinones as novel monoamine oxidase type A inhibitors.	2005-03	16787307
Neuroendocrine predictors of the evolution of depression.	2005	16156385
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.	2004-09	15178694
A high-performance liquid chromatography method with photodiode-array UV detection for therapeutic drug monitoring of the nontricyclic antidepressant drugs.	2003-10	14508379
Highly efficient CuI-catalyzed coupling of aryl bromides with oxazolidinones using Buchwald's protocol: a short route to linezolid and toloxatone.	2003-04-03	12659549
Synthesis and biological evaluation of enantiomerically pure pyrrolyl-oxazolidinones as a new class of potent and selective monoamine oxidase type A inhibitors.	2003-03	12620419
3-(1H-Pyrrol-1-yl)-2-oxazolidinones as reversible, highly potent, and selective inhibitors of monoamine oxidase type A.	2002-03-14	11881986
The clinical pharmacology of depressive states.	2002-03	22034133
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.	1990-12	1705137

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

HUMORYL

Preferred Name

English

TOLOXATONE [MART.]

Common Name

English

TOLOXATONE [MI]

Common Name

English

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

Systematic 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