BEFLOXATONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C15H18F3NO5
Molecular Weight	349.3023
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC[C@H]1CN(C(=O)O1)C2=CC=C(OCC[C@@H](O)C(F)(F)F)C=C2

InChI

InChIKey=IALVDLPLCLFBCF-CHWSQXEVSA-N

InChI=1S/C15H18F3NO5/c1-22-9-12-8-19(14(21)24-12)10-2-4-11(5-3-10)23-7-6-13(20)15(16,17)18/h2-5,12-13,20H,6-9H2,1H3/t12-,13-/m1/s1

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Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16160936 | https://adisinsight.springer.com/drugs/800001426

Befloxatone (MD-370,503) is a reversible inhibitor of monoamine oxidase A that was developed by Synthelabo for the treatment of depression, social phobias, and panic disorders. This drug participated in phase III clinical trials in France for depression. In addition participated in phase II for smoking cessation, anxiety disorders. Befloxatone has a good safety profile, lacking sedative, convulsant, anticholinergic and cardiovascular effects. However, all studies were discontinued.

Originator

Approval Year

PubMed

Title	Date	PubMed
Preclinical profile of befloxatone, a new reversible MAO-A inhibitor.	1998 Dec	10333983
Inhibitors alter the spectrum and redox properties of monoamine oxidase A.	2002 Dec 16	12445480
Comparative effects of dehydropirlindole and other compounds on rat brain monoamine oxidase type A.	2002 Jan	11853123
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
Mapping the cerebral monoamine oxidase type A: positron emission tomography characterization of the reversible selective inhibitor [11C]befloxatone.	2003 May	12606609
Synthesis and in vivo imaging properties of [11C]befloxatone: a novel highly potent positron emission tomography ligand for mono-amine oxidase-A.	2003 May 19	12729662
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
Acute inhibition of cardiac monoamine oxidase A after tobacco smoke inhalation: validation study of [11C]befloxatone in rats followed by a positron emission tomography application in baboons.	2005 Jul	15833896
Genetic polymorphisms in dopamine-related genes and smoking cessation in women: a prospective cohort study.	2007 Apr 28	17466074
Calcium-sensitive regulation of monoamine oxidase-A contributes to the production of peroxyradicals in hippocampal cultures: implications for Alzheimer disease-related pathology.	2007 Sep 16	17868476
Cerebral monoamine oxidase A inhibition in tobacco smokers confirmed with PET and [11C]befloxatone.	2009 Feb	19142115
In vivo quantification of monoamine oxidase A in baboon brain: a PET study using [(11)C]befloxatone and the multi-injection approach.	2010 Apr	19920845
Electrophysiological characterization of harmane-induced activation of mesolimbic dopamine neurons.	2010 Mar 10	20026027

Patents

Sample Use Guides

In Vivo Use Guide

To assess the effects of single oral doses of befloxatone (5, 10, and 20 mg) on psychomotor performance and memory, a randomized, double-blind, five-way, crossover study with both placebo and amitriptyline (50 mg) was carried out in 15 healthy male volunteers.

Route of Administration: Oral

Name

Type

Language

BEFLOXATONE

Official Name

English

BEFLOXATONE [MI]

Common Name

English

befloxatone [INN]

Common Name

English

BEFLOXATONE [MART.]

Common Name

English

Befloxatone [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C667