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98769-81-4 molecular structure
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(2S)-2-[(S)-2-ethoxyphenoxy(phenyl)methyl]morpholine

ChemBase ID: 119
Molecular Formular: C19H23NO3
Molecular Mass: 313.39082
Monoisotopic Mass: 313.1677936
SMILES and InChIs

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

Cite this record

CBID:119 http://www.chembase.cn/molecule-119.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
98769-81-4
PubChem SID
160963582
46504845
PubChem CID
65856

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 65856 external link
DrugBank DB00234 external link
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) 0.9233303  LogD (pH = 7.4) 2.6492774 
Log P 3.2758145  Molar Refractivity 89.4849 cm3
Polarizability 35.656822 Å3 Polar Surface Area 39.72 Å2
Rotatable Bonds Lipinski's Rule of Five true 
Log P 3.06  LOG S -4.15 
Solubility (Water) 2.23e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Solubility
8 mg/mL (Mesylate salt) expand Show data source
Hydrophobicity(logP)
3.1 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00234 external link
Item Information
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

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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
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