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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.CCOC1=C(O[C@H]([C@@H]2CNCCO2)C3=CC=CC=C3)C=CC=C1

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 C4H6O4
Molecular Weight 118.088
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C19H23NO3
Molecular Weight 313.3908
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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.

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.08 nM [Ki]
PubMed

PubMed

TitleDatePubMed
Reboxetine may be helpful in the treatment of amphetamine withdrawal.
2004 Jul
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
Residual symptoms in depressed patients after treatment with fluoxetine or reboxetine.
2005 Nov
[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
Transvaginal repair of genital prolapse: preliminary results of a new tension-free vaginal mesh (Prolift technique)--a case series multicentric study.
2007 Jul
Pelvic arterial embolization in the setting of acute hemorrhage as a result of the anterior Prolift procedure.
2007 Jul
Laparoscopic sacral colpopexy with Gynemesh as graft material--experience and results.
2007 Sep-Oct
Complications and patient satisfaction after transobturator anterior and/or posterior tension-free vaginal polypropylene mesh for pelvic organ prolapse.
2008
Total Prolift System surgery for treatment posthysterectomy vaginal vault prolapse--do we treat both anatomy and function?
2008 Dec
One-year anatomic and quality-of-life outcomes after the Prolift procedure for treatment of posthysterectomy prolapse.
2008 Dec
Does the Prolift system cause dyspareunia?
2008 Dec
[Clinical study on concomitant surgery for stress urinary incontinence and pelvic organ prolapse].
2008 Oct 15
[Occult stress incontinence identified by preoperative urodynamic study in women with severe pelvic organ prolapse].
2008 Sep
A prospective study to evaluate the anatomic and functional outcome of a transobturator mesh kit (prolift anterior) for symptomatic cystocele repair.
2008 Sep-Oct
Implants in operative therapy in women with pelvic organ prolapse--two years of experience.
2009
Vaginal vault prolapse.
2009
Vaginal repair of cystocele with anterior wall mesh via transobturator route: efficacy and complications with up to 3-year followup.
2009
[Surgical treatment of female pelvic organ prolapse at the Clinic of Obstetrics and Gynecology, Hospital of Kaunas University of Medicine].
2009
Psychopharmacology of ADHD in pediatrics: current advances and issues.
2009
[Transvaginal repair of genital prolapse with prolift: a standardized surgery?].
2009 Apr
Perineal approach to vascular anatomy during transobturator cystocele repair.
2009 Apr
[Transvaginal repair of genital prolapse with Prolift: evaluation of safety and learning curve].
2009 Feb
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
[Clinical observation on quality of life of two different operative methods of total pelvic floor reconstruction.].
2009 Nov
A serious complication following placement of posterior Prolift.
2009 Nov
Anatomic outcomes of vaginal mesh procedure (Prolift) compared with uterosacral ligament suspension and abdominal sacrocolpopexy for pelvic organ prolapse: a Fellows' Pelvic Research Network study.
2009 Nov
Synthetic graft use in vaginal prolapse surgery: objective and subjective outcomes.
2009 Nov
Short term impact on female sexual function of pelvic floor reconstruction with the Prolift procedure.
2009 Nov
Laparoscopic sacrohysteropexy and myomectomy for uterine prolapse: a case report and review of the literature.
2009 Nov 3
Trocar-guided total tension-free vaginal mesh repair of post-hysterectomy vaginal vault prolapse.
2009 Oct
Laparoscopic apical mesh excision for deep dyspareunia caused by mesh banding in the vaginal apex.
2009 Sep
[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
[Correlation between stress urinary incontinence or urgency and anterior compartment defect before and after surgical treatment].
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
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
Does trocar-guided tension-free vaginal mesh (Prolift) repair provoke prolapse of the unaffected compartments?
2010 Mar
Optimal primary minimally invasive treatment for patients with stress urinary incontinence and symptomatic pelvic organ prolapse: tension free slings with colporrhaphy, or Prolift with the tension free midurethral sling?
2010 May
[Postoperative pain after transvaginal repair of pelvic organ prolapse with or without mesh].
2010 Nov
[Patent for medical device: from design to marketing (example of Prolift®)].
2010 Oct
Transurethral and suprapubic mesh resection after Prolift bladder perforation: a case report.
2010 Oct
Now or later...Does timing of a midurethral sling in relation to transvaginal prolapse repair affect continence outcomes at 1 year?
2010 Sep
Antidepressant drugs transactivate TrkB neurotrophin receptors in the adult rodent brain independently of BDNF and monoamine transporter blockade.
2011
Discovery of novel selective norepinephrine inhibitors: 1-(2-morpholin-2-ylethyl)-3-aryl-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxides (WYE-114152).
2011 Oct 13
Patents

Sample Use Guides

In Vivo Use Guide
Phase III study: 4-10 mg once daily for 14 weeks
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Tue Oct 22 01:38:08 UTC 2019
Edited
by admin
on Tue Oct 22 01:38:08 UTC 2019
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 Tue Oct 22 01:38:08 UTC 2019 , Edited by admin on Tue Oct 22 01:38:08 UTC 2019
Code System Code Type Description
EVMPD
SUB34044
Created by admin on Tue Oct 22 01:38:08 UTC 2019 , Edited by admin on Tue Oct 22 01:38:08 UTC 2019
PRIMARY
ChEMBL
CHEMBL180101
Created by admin on Tue Oct 22 01:38:08 UTC 2019 , Edited by admin on Tue Oct 22 01:38:08 UTC 2019
PRIMARY
PUBCHEM
24754241
Created by admin on Tue Oct 22 01:38:08 UTC 2019 , Edited by admin on Tue Oct 22 01:38:08 UTC 2019
PRIMARY
CAS
635724-55-9
Created by admin on Tue Oct 22 01:38:08 UTC 2019 , Edited by admin on Tue Oct 22 01:38:08 UTC 2019
PRIMARY
NCI_THESAURUS
C87613
Created by admin on Tue Oct 22 01:38:08 UTC 2019 , Edited by admin on Tue Oct 22 01:38:08 UTC 2019
PRIMARY
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ACTIVE MOIETY