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Manifaxine (developmental code name GW-320,659) is a norepinephrine–dopamine reuptake inhibitor developed by
The Grignard reaction between 3,5-difluorobenzonitrile 4248-63-1(1) and ethylmangensium bromide gives 3,5-difluoropropiophenone 35306-45-5(2). Halogenation with molecular bromine occurs at the alpha-keto position providing 2-bromo-3',5'-difluoropropiophenone 35306-46-6(3). Intermolecular ring formation with DL-Alaninol (2-Aminopropanol) 168-72-5completed the synthesis of Manifaxine (4).
GlaxoSmithKline
GSK plc, formerly GlaxoSmithKline plc, is a British multinational pharmaceutical and biotechnology company with global headquarters in London, England. Established in 2000 by a merger of Glaxo Wellcome and SmithKline Beecham. GSK is the ten ...
through structural modification
Molecular modification is chemical alteration of a known and previously characterized lead compound for the purpose of enhancing its usefulness as a drug. This could mean enhancing its specificity for a particular body target site, increasing its ...
of radafaxine
Radafaxine (developmental code name GW-353,162), also known as (2''S'',3''S'')-hydroxybupropion or (''S'',''S'')-hydroxybupropion, is a norepinephrine–dopamine reuptake inhibitor (NDRI) which was under development by GlaxoSmithKline in the 20 ...
, an isomer
In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers.
Iso ...
of hydroxybupropion
Hydroxybupropion (code name BW 306U), or 6-hydroxybupropion, is the major active metabolite of the antidepressant and smoking cessation drug bupropion. It is formed from bupropion by the liver enzyme CYP2B6 during first-pass metabolism. With ora ...
and one of the active metabolite An active metabolite is an active form of a drug after it has been processed by the body.
Metabolites of drugs
An active metabolite results when a drug is metabolized by the body into a modified form which continues to produce effects in the body ...
s of bupropion. Manifaxine was researched for treatment of attention deficit hyperactivity disorder
Attention deficit hyperactivity disorder (ADHD) is a neurodevelopmental disorder characterised by excessive amounts of inattention, hyperactivity, and impulsivity that are pervasive, impairing in multiple contexts, and otherwise age-inap ...
(ADHD) and obesity
Obesity is a medical condition, sometimes considered a disease, in which excess body fat has accumulated to such an extent that it may negatively affect health. People are classified as obese when their body mass index (BMI)—a person's we ...
and was found to be safe, reasonably effective, and well-tolerated for both applications. However, no results were reported following these initial trials and development was discontinued.Synthesis
The Grignard reaction between 3,5-difluorobenzonitrile 4248-63-1(1) and ethylmangensium bromide gives 3,5-difluoropropiophenone 35306-45-5(2). Halogenation with molecular bromine occurs at the alpha-keto position providing 2-bromo-3',5'-difluoropropiophenone 35306-46-6(3). Intermolecular ring formation with DL-Alaninol (2-Aminopropanol) 168-72-5completed the synthesis of Manifaxine (4).See also
* 3,5-Difluoromethcathinone *3-Fluorophenmetrazine
3-Fluorophenmetrazine (also known as 3-FPM, 3-FPH and PAL-593) is a phenylmorpholine-based stimulant and fluorinated analogue of phenmetrazine that has been sold online as a designer drug.
Chemistry
3-Fluorophenmetrazine is a fluorinated anal ...
References
Fluoroarenes GSK plc brands Substituted amphetamines Phenylmorpholines Norepinephrine–dopamine reuptake inhibitors Stimulants Tertiary alcohols {{Nervous-system-drug-stub