CAS 98769-81-4|(2S)-2-[(S)-2-ethoxyphenoxy(phenyl)methyl]morpholine|reboxetine|reboxetine|Edronax|Reboxetine mesylate|Vestra|Davedax|Prolift|Solvex|Norebox|Reboxetine

General Information

Structure

Molecular Formula

C₁₉H₂₃NO₃

Molecular Mass

313.39082

Exact Mass

313.1677936

Charge

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

Canonic Smiles

CCOc1ccccc1O[C@@H](c1ccccc1)[C@H]1OCCNC1

Isomeric Smiles

O1[C@H]([C@@H](Oc2c(OCC)cccc2)c2ccccc2)CNCC1

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

0.9233303

LogD (pH = 7.4)

2.6492774

Log P

3.2758145

Molar Refractivity

89.4849

Polarizability

35.656822

Polar Surface Area

39.72

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

3.06

LOG S

-4.15

Solubility (Water)

2.23e-02 g/l

Data Source

Academic Data

Data Source

Names and Identifiers

IUPAC name

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

Synonyms

reboxetineReboxetine mesylateReboxetine

IUPAC Traditional name

reboxetine

Brand Name

EdronaxVestraDavedaxProliftSolvexNorebox

Names and Identifiers

Registration numbers

PubChem SID

46504845160963582

PubChem CID

65856

CAS Number

98769-81-4

Registration numbers

Properties

Physical Property

Solubility

8 mg/mL (Mesylate salt)

Hydrophobicity(logP)

3.1

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule 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]

External Links

• [Wikipedia]

Molecule Details

References

PubChem Literature

From Data Sources

• 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

References

Bioactivity

PubChem BioAssay

Bioactivity

Navigation

General Information

Calculated Properties

• RDKit

• JChem

• ALOGPS 2.1

Data Source

• Academic Data

Names and Identifiers

• IUPAC name

• Synonyms

• IUPAC Traditional name

• Brand Name

Registration numbers

• PubChem SID

• PubChem CID

• CAS Number

• Physical Property

• DrugBank

• PubChem Literature

• From Data Sources

Bioactivity

• PubChem BioAssay

IUPAC name

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

Synonyms

reboxetineReboxetine mesylateReboxetine

IUPAC Traditional name

reboxetine

Brand Name

EdronaxVestraDavedaxProliftSolvexNorebox

PubChem SID

46504845160963582

CAS Number

98769-81-4

Physical Property

Solubility

8 mg/mL (Mesylate salt)

Hydrophobicity(logP)

3.1

DrugBank

DB00234

Drug Groups

approved; investigational

Description

Indication

For the treatment of clinical depression.

Pharmacology

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

• 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]

External Links

• [Wikipedia]

From Data Sources

• 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

Molecule

ID:119