U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
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
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).
2011-10-13
Antidepressant drugs transactivate TrkB neurotrophin receptors in the adult rodent brain independently of BDNF and monoamine transporter blockade.
2011
[Postoperative pain after transvaginal repair of pelvic organ prolapse with or without mesh].
2010-11
Pelvic magnetic resonance imaging for assessment of the efficacy of the Prolift system for pelvic organ prolapse.
2010-11
Reboxetine for acute treatment of major depression: systematic review and meta-analysis of published and unpublished placebo and selective serotonin reuptake inhibitor controlled trials.
2010-10-12
[Patent for medical device: from design to marketing (example of Prolift®)].
2010-10
Transurethral and suprapubic mesh resection after Prolift bladder perforation: a case report.
2010-10
Now or later...Does timing of a midurethral sling in relation to transvaginal prolapse repair affect continence outcomes at 1 year?
2010-09
Vaginal hysterectomy at the time of transvaginal mesh placement.
2010-09
[Transvaginal repair of genital prolapse using the Prolift technique: a prospective study].
2010-09
Permeation of chlorothalonil through nitrile gloves: collection solvent effects in the closed-loop permeation method.
2010-07-15
Midterm prospective evaluation of TVT-Secur reveals high failure rate.
2010-07
Mid-term results of pelvic organ prolapse repair using a transvaginal mesh: the experience in Sherbooke, Quebec.
2010-06
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?
2010-05
[Changes in the length of implanted mesh after reconstructive surgery of the anterior vaginal wall].
2010-04
[Prolene mesh comparing with sacrospinal fixation in the treatment of genital prolapse in women. Prospective multicentre randomized study].
2010-04
[Correlation between stress urinary incontinence or urgency and anterior compartment defect before and after surgical treatment].
2010-04
Transvaginal mesh repair of anterior and posterior vaginal wall prolapse: a clinical and ultrasonographic study.
2010-04
Successful management of depression with reboxetine in a patient who developed Parkinsonism related to paroxetine use.
2010-04
Anatomical and functional outcomes of posterior intravaginal slingplasty for the treatment of vaginal vault or uterine prolapse: a prospective, multicenter study.
2010-03
Does trocar-guided tension-free vaginal mesh (Prolift) repair provoke prolapse of the unaffected compartments?
2010-03
Permeation of herbicidal dichlobenil from a Casoron formulation through nitrile gloves.
2010-02
One-year outcome of concurrent anterior and posterior transvaginal mesh surgery for treatment of advanced urogenital prolapse: case series.
2009-11-16
Laparoscopic sacrohysteropexy and myomectomy for uterine prolapse: a case report and review of the literature.
2009-11-03
[Clinical observation on quality of life of two different operative methods of total pelvic floor reconstruction.].
2009-11
A serious complication following placement of posterior Prolift.
2009-11
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.
2009-11
Synthetic graft use in vaginal prolapse surgery: objective and subjective outcomes.
2009-11
Short term impact on female sexual function of pelvic floor reconstruction with the Prolift procedure.
2009-11
Trocar-guided total tension-free vaginal mesh repair of post-hysterectomy vaginal vault prolapse.
2009-10
Laparoscopic apical mesh excision for deep dyspareunia caused by mesh banding in the vaginal apex.
2009-09
De novo stress incontinence and pelvic muscle symptoms after transvaginal mesh repair.
2009-07
Changes in levator ani muscle after vaginal hysterectomy and prolapse repair using the Total Prolift procedure.
2009-07
[Transvaginal repair of genital prolapse with prolift: a standardized surgery?].
2009-04
Perineal approach to vascular anatomy during transobturator cystocele repair.
2009-04
[Choice of a surgical treatment of genital prolapse in women].
2009-03-03
[Transvaginal repair of genital prolapse with Prolift: evaluation of safety and learning curve].
2009-02
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
The combined dexamethasone/CRH Test (DEX/CRH test) and prediction of acute treatment response in major depression.
2009
Outcome of treatment of anterior vaginal wall prolapse and stress urinary incontinence with transobturator tension-free vaginal mesh (prolift) and concomitant tension-free vaginal tape-obturator.
2009
Total Prolift System surgery for treatment posthysterectomy vaginal vault prolapse--do we treat both anatomy and function?
2008-12
[Clinical study on concomitant surgery for stress urinary incontinence and pelvic organ prolapse].
2008-10-15
[Occult stress incontinence identified by preoperative urodynamic study in women with severe pelvic organ prolapse].
2008-09
Fixed combinations in the management of hypertension: perspectives on lercanidipine-enalapril.
2008
Efficacy and tolerability of reboxetine compared with imipramine in a double-blind study in patients suffering from major depressive offsodes.
1997-04
Pharmacokinetics of reboxetine in healthy volunteers. Single oral doses, linearity and plasma protein binding.
1995-08
Patents

Sample Use Guides

Phase III study: 4-10 mg once daily for 14 weeks
Route of Administration: Oral
Name Type Language
(S,S)-REBOXETINE SUCCINATE
Preferred Name English
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
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 Mon Mar 31 18:31:02 GMT 2025 , Edited by admin on Mon Mar 31 18:31:02 GMT 2025
Code System Code Type Description
SMS_ID
100000127897
Created by admin on Mon Mar 31 18:31:02 GMT 2025 , Edited by admin on Mon Mar 31 18:31:02 GMT 2025
PRIMARY
EVMPD
SUB34044
Created by admin on Mon Mar 31 18:31:02 GMT 2025 , Edited by admin on Mon Mar 31 18:31:02 GMT 2025
PRIMARY
EPA CompTox
DTXSID10979793
Created by admin on Mon Mar 31 18:31:02 GMT 2025 , Edited by admin on Mon Mar 31 18:31:02 GMT 2025
PRIMARY
USAN
TT-90
Created by admin on Mon Mar 31 18:31:02 GMT 2025 , Edited by admin on Mon Mar 31 18:31:02 GMT 2025
PRIMARY
ChEMBL
CHEMBL180101
Created by admin on Mon Mar 31 18:31:02 GMT 2025 , Edited by admin on Mon Mar 31 18:31:02 GMT 2025
PRIMARY
PUBCHEM
24754241
Created by admin on Mon Mar 31 18:31:02 GMT 2025 , Edited by admin on Mon Mar 31 18:31:02 GMT 2025
PRIMARY
CAS
635724-55-9
Created by admin on Mon Mar 31 18:31:02 GMT 2025 , Edited by admin on Mon Mar 31 18:31:02 GMT 2025
PRIMARY
FDA UNII
XQO13W6OCH
Created by admin on Mon Mar 31 18:31:02 GMT 2025 , Edited by admin on Mon Mar 31 18:31:02 GMT 2025
PRIMARY
NCI_THESAURUS
C87613
Created by admin on Mon Mar 31 18:31:02 GMT 2025 , Edited by admin on Mon Mar 31 18:31:02 GMT 2025
PRIMARY