Reboxetine

• Catalog No.: DB00234
• CAS Number: 98769-81-4
• M. F.: C19H23NO3
• M. W.: 313.39082

SYNONYMS

• IUPAC name: (2S)-2-[(S)-2-ethoxyphenoxy(phenyl)methyl]morpholine
• IUPAC Traditional name: reboxetine
• Brand Name: Prolift; Davedax; Edronax; Vestra; Norebox; Solvex
• Synonyms: Reboxetine mesylate; reboxetine

DATABASE IDS

• PubChem SID: 46504845
• PubChem CID: 65856
• CAS Number: 98769-81-4

PROPERTIES

• Hydrophobicity(logP): 3.1
• Solubility: 8 mg/mL (Mesylate salt)

DETAILS

Description (English)

• Drug Groups: approved; investigational
• Description: Reboxetine is an antidepressant drug used in the treatment of clinical depression, panic disorder and ADD/ADHD. Its mesylate (i.e. methanesulfonate) salt is sold under tradenames including Edronax, Norebox, Prolift, Solvex, Davedax or Vestra. Reboxetine has two chiral centers, but it only exists as two enantiomers, (R,R)-(-)- and (S,S)-(+)-reboxetine.
• Indication: For the treatment of clinical depression.
• Pharmacology: Reboxetine is a selective noradrenaline reuptake inhibitor (NaRI), the first drug of new antidepressant class. Reboxetine is an a-ariloxybenzyl derivative of morpholine. Reboxetine is primarily used to treat depression but has also been found useful in the treatment of narcolepsy and panic disorders.
• Toxicity: Reports of seizures (rare) have been reported
• Affected Organisms: Humans and other mammals
• Biotransformation: Reboxetine is metabolized by dealkylation, hydroxylation and oxidation followed; by glucuronide or sulphate conjugation. It is metabolized by the cytochrome P450; CYP isoenzyme 3A4.
• Absorption: Reboxetine is rapidly and extensively absorbed following oral administration.
• Half Life: 12.5 hours
• Protein Binding: 98%
• References: Fleishaker JC: Clinical pharmacokinetics of reboxetine, a selective norepinephrine reuptake inhibitor for the treatment of patients with depression. Clin Pharmacokinet. 2000 Dec;39(6):413-27. [Pubmed] ; Edwards DM, Pellizzoni C, Breuel HP, Berardi A, Castelli MG, Frigerio E, Poggesi I, Rocchetti M, Dubini A, Strolin Benedetti M: Pharmacokinetics of reboxetine in healthy volunteers. Single oral doses, linearity and plasma protein binding. Biopharm Drug Dispos. 1995 Aug;16(6):443-60. [Pubmed] ; Wienkers LC, Allievi C, Hauer MJ, Wynalda MA: Cytochrome P-450-mediated metabolism of the individual enantiomers of the antidepressant agent reboxetine in human liver microsomes. Drug Metab Dispos. 1999 Nov;27(11):1334-40. [Pubmed] ; Kasper S, el Giamal N, Hilger E: Reboxetine: the first selective noradrenaline re-uptake inhibitor. Expert Opin Pharmacother. 2000 May;1(4):771-82. [Pubmed] ; Fleishaker JC: Clinical pharmacokinetics of reboxetine, a selective norepinephrine reuptake inhibitor for the treatment of patients with depression. Clin Pharmacokinet. 2000 Dec;39(6):413-27. [Pubmed]
• External Links: Wikipedia

REFERENCES

• Edwards DM, Pellizzoni C, Breuel HP, Berardi A, Castelli MG, Frigerio E, Poggesi I, Rocchetti M, Dubini A, Strolin Benedetti M: Pharmacokinetics of reboxetine in healthy volunteers. Single oral doses, linearity and plasma protein binding. Biopharm Drug Dispos. 1995 Aug;16(6):443-60. Pubmed
• Wienkers LC, Allievi C, Hauer MJ, Wynalda MA: Cytochrome P-450-mediated metabolism of the individual enantiomers of the antidepressant agent reboxetine in human liver microsomes. Drug Metab Dispos. 1999 Nov;27(11):1334-40. Pubmed
• Kasper S, el Giamal N, Hilger E: Reboxetine: the first selective noradrenaline re-uptake inhibitor. Expert Opin Pharmacother. 2000 May;1(4):771-82. Pubmed
• Fleishaker JC: Clinical pharmacokinetics of reboxetine, a selective norepinephrine reuptake inhibitor for the treatment of patients with depression. Clin Pharmacokinet. 2000 Dec;39(6):413-27. Pubmed
• Fleishaker JC: Clinical pharmacokinetics of reboxetine, a selective norepinephrine reuptake inhibitor for the treatment of patients with depression. Clin Pharmacokinet. 2000 Dec;39(6):413-27. Pubmed