(2S)-2-[(S)-2-ethoxyphenoxy(phenyl)methyl]morpholine

• ChemBase ID: 119
• Molecular Formular: C19H23NO3
• Molecular Mass: 313.39082
• Monoisotopic Mass: 313.1677936
• SMILES: O1[C@H]([C@@H](Oc2c(OCC)cccc2)c2ccccc2)CNCC1
• Canonical SMILES: CCOc1ccccc1O[C@@H](c1ccccc1)[C@H]1OCCNC1
• InChI: InChI=1S/C19H23NO3/c1-2-21-16-10-6-7-11-17(16)23-19(15-8-4-3-5-9-15)18-14-20-12-13-22-18/h3-11,18-20H,2,12-14H2,1H3/t18-,19-/m0/s1
• InChIKey: CBQGYUDMJHNJBX-OALUTQOASA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 98769-81-4
• PubChem SID: 46504845; 160963582
• PubChem CID: 65856

CALCULATED PROPERTIES

JChem

• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 0.9233303
• LogD (pH = 7.4): 2.6492774
• Log P: 3.2758145
• Molar Refractivity: 89.4849 cm^3
• Polarizability: 35.656822 Å^3
• Polar Surface Area: 39.72 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.06
• LOG S: -4.15
• Solubility (Water): 2.23e-02 g/l

PROPERTIES

Physical Property

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

DETAILS

DrugBank - DB00234

• 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