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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H23NO3.C4H6O4
Molecular Weight 431.4789
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ESREBOXETINE SUCCINATE

SMILES

OC(=O)CCC(O)=O.[H][C@]1(CNCCO1)[C@@H](OC2=C(OCC)C=CC=C2)C3=CC=CC=C3

InChI

InChIKey=YXZTUOWIYOESGT-HLRBRJAUSA-N
InChI=1S/C19H23NO3.C4H6O4/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;5-3(6)1-2-4(7)8/h3-11,18-20H,2,12-14H2,1H3;1-2H2,(H,5,6)(H,7,8)/t18-,19-;/m0./s1

HIDE SMILES / InChI

Molecular Formula C19H23NO3
Molecular Weight 313.3908
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C4H6O4
Molecular Weight 118.088
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Esreboxetine (PNU-165442G) is the (S,S)-(+)-enantiomer of antidepressant reboxetine, a selective norepinephrine reuptake inhibitor. The (S,S)-enantiomer is a more potent inhibitor of norepinephrine transporter than (R,R)-enantiomer. Esreboxetine was being developed by Pfizer, primarily for the treatment of fibromyalgia.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.08 nM [Ki]
PubMed

PubMed

TitleDatePubMed
Pharmacokinetics of reboxetine in healthy volunteers. Single oral doses, linearity and plasma protein binding.
1995 Aug
Efficacy and tolerability of reboxetine compared with imipramine in a double-blind study in patients suffering from major depressive offsodes.
1997 Apr
Cytochrome P-450-mediated metabolism of the individual enantiomers of the antidepressant agent reboxetine in human liver microsomes.
1999 Nov
Reboxetine versus imipramine in the treatment of elderly patients with depressive disorders: a double-blind randomised trial.
1999 Oct
Reversal of tetrabenazine induced depression by selective noradrenaline (norepinephrine) reuptake inhibition.
1999 Oct
Clinical pharmacokinetics of reboxetine, a selective norepinephrine reuptake inhibitor for the treatment of patients with depression.
2000 Dec
Urinary retention with reboxetine-fluoxetine combination in a young man.
2000 Dec
Reboxetine: the first selective noradrenaline re-uptake inhibitor.
2000 May
Reboxetine: a pharmacologically potent, selective, and specific norepinephrine reuptake inhibitor.
2000 May 1
Antifungal properties of selective serotonin reuptake inhibitors against Aspergillus species in vitro.
2001 Dec
Cocaine and amphetamine increase extracellular dopamine in the nucleus accumbens of mice lacking the dopamine transporter gene.
2001 May 1
Acute dystonic reaction in an elderly patient with mood disorder after titration of paroxetine: possible mechanisms and implications for clinical care.
2002 Dec
Effect of repeated treatment with reboxetine on the central alpha 1-adrenergic and dopaminergic receptors.
2002 Nov-Dec
Acute akinetic crisis with marked cognitive impairment due to Valproate treatment.
2003 Apr
The promises and pitfalls of reboxetine.
2003 Winter
Reboxetine may be helpful in the treatment of amphetamine withdrawal.
2004 Jul
Norepinephrine-deficient mice lack responses to antidepressant drugs, including selective serotonin reuptake inhibitors.
2004 May 25
Reboxetine for the treatment of patients with Cocaine Dependence Disorder.
2005 Apr
Contrasting Fos expression induced by acute reboxetine and fluoxetine in the rat forebrain: neuroanatomical substrates for the antidepressant effect.
2005 Jan
Nitrile glove permeation of benomyl.
2006 Apr
[Trazodone for the treatment of behavioral and psychological symptoms of dementia (BPSD) in Alzheimer's disease: a retrospective study focused on the aggression and negativism in caregiving situations].
2006 Jun
Monotherapy with reboxetine in amphetamine withdrawal syndrome.
2006 Sep 30
[Advanced mesh implants for vaginal pelvic floor reconstruction: report of 100 prolift operations].
2007 Dec
[Prolift system in the correction of female genital prolapse].
2007 Sep
Laparoscopic sacral colpopexy with Gynemesh as graft material--experience and results.
2007 Sep-Oct
Hormonal influences on cardiovascular norepinephrine transporter responses in healthy women.
2008 Apr
Total Prolift System surgery for treatment posthysterectomy vaginal vault prolapse--do we treat both anatomy and function?
2008 Dec
Short-term outcome after transvaginal mesh repair of pelvic organ prolapse.
2008 Jun
What is the mechanism of microalbuminuria in diabetes: a role for the glomerular endothelium?
2008 May
[Choice of a surgical treatment of genital prolapse in women].
2008 Nov-Dec
Implants in operative therapy in women with pelvic organ prolapse--two years of experience.
2009
Vaginal repair of cystocele with anterior wall mesh via transobturator route: efficacy and complications with up to 3-year followup.
2009
Psychopharmacology of ADHD in pediatrics: current advances and issues.
2009
De novo stress incontinence and pelvic muscle symptoms after transvaginal mesh repair.
2009 Jul
Changes in levator ani muscle after vaginal hysterectomy and prolapse repair using the Total Prolift procedure.
2009 Jul
A serious complication following placement of posterior Prolift.
2009 Nov
Short term impact on female sexual function of pelvic floor reconstruction with the Prolift procedure.
2009 Nov
[Changes in the length of implanted mesh after reconstructive surgery of the anterior vaginal wall].
2010 Apr
[Prolene mesh comparing with sacrospinal fixation in the treatment of genital prolapse in women. Prospective multicentre randomized study].
2010 Apr
Successful management of depression with reboxetine in a patient who developed Parkinsonism related to paroxetine use.
2010 Apr
Permeation of herbicidal dichlobenil from a Casoron formulation through nitrile gloves.
2010 Feb
Permeation of chlorothalonil through nitrile gloves: collection solvent effects in the closed-loop permeation method.
2010 Jul 15
One-year outcome of concurrent anterior and posterior transvaginal mesh surgery for treatment of advanced urogenital prolapse: case series.
2010 Jul-Aug
Anatomical and functional outcomes of posterior intravaginal slingplasty for the treatment of vaginal vault or uterine prolapse: a prospective, multicenter study.
2010 Mar
Reboxetine for acute treatment of major depression: systematic review and meta-analysis of published and unpublished placebo and selective serotonin reuptake inhibitor controlled trials.
2010 Oct 12
Now or later...Does timing of a midurethral sling in relation to transvaginal prolapse repair affect continence outcomes at 1 year?
2010 Sep
Patents

Sample Use Guides

Phase III study: 4-10 mg once daily for 14 weeks
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Wed Jul 05 23:58:31 UTC 2023
Edited
by admin
on Wed Jul 05 23:58:31 UTC 2023
Record UNII
XQO13W6OCH
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ESREBOXETINE SUCCINATE
USAN  
USAN  
Official Name English
ESREBOXETINE SUCCINATE [USAN]
Common Name English
PNU-165442G
Code English
(+)-(2S)-2-((S)-(2-ETHOXYPHENOXY)PHENYLMETHYL)MORPHOLINE HYDROGEN BUTANEDIOATE
Systematic Name English
(S,S)-REBOXETINE SUCCINATE
Common Name English
BUTANEDIOIC ACID, COMPD. WITH (2S)-2-((S)-(2-ETHOXYPHENOXY)PHENYLMETHYL)MORPHOLINE (1:1)
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C265
Created by admin on Wed Jul 05 23:58:31 UTC 2023 , Edited by admin on Wed Jul 05 23:58:31 UTC 2023
Code System Code Type Description
SMS_ID
100000127897
Created by admin on Wed Jul 05 23:58:31 UTC 2023 , Edited by admin on Wed Jul 05 23:58:31 UTC 2023
PRIMARY
EVMPD
SUB34044
Created by admin on Wed Jul 05 23:58:31 UTC 2023 , Edited by admin on Wed Jul 05 23:58:31 UTC 2023
PRIMARY
EPA CompTox
DTXSID10979793
Created by admin on Wed Jul 05 23:58:31 UTC 2023 , Edited by admin on Wed Jul 05 23:58:31 UTC 2023
PRIMARY
USAN
TT-90
Created by admin on Wed Jul 05 23:58:31 UTC 2023 , Edited by admin on Wed Jul 05 23:58:31 UTC 2023
PRIMARY
ChEMBL
CHEMBL180101
Created by admin on Wed Jul 05 23:58:31 UTC 2023 , Edited by admin on Wed Jul 05 23:58:31 UTC 2023
PRIMARY
PUBCHEM
24754241
Created by admin on Wed Jul 05 23:58:31 UTC 2023 , Edited by admin on Wed Jul 05 23:58:31 UTC 2023
PRIMARY
CAS
635724-55-9
Created by admin on Wed Jul 05 23:58:31 UTC 2023 , Edited by admin on Wed Jul 05 23:58:31 UTC 2023
PRIMARY
FDA UNII
XQO13W6OCH
Created by admin on Wed Jul 05 23:58:31 UTC 2023 , Edited by admin on Wed Jul 05 23:58:31 UTC 2023
PRIMARY
NCI_THESAURUS
C87613
Created by admin on Wed Jul 05 23:58:31 UTC 2023 , Edited by admin on Wed Jul 05 23:58:31 UTC 2023
PRIMARY
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ACTIVE MOIETY