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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 No
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 No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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
Reboxetine for the treatment of patients with Cocaine Dependence Disorder.
2005 Apr
[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
Fixed combinations in the management of hypertension: perspectives on lercanidipine-enalapril.
2008
Hormonal influences on cardiovascular norepinephrine transporter responses in healthy women.
2008 Apr
One-year anatomic and quality-of-life outcomes after the Prolift procedure for treatment of posthysterectomy prolapse.
2008 Dec
Vaginal repair of cystocele with anterior wall mesh via transobturator route: efficacy and complications with up to 3-year followup.
2009
The combined dexamethasone/CRH Test (DEX/CRH test) and prediction of acute treatment response in major depression.
2009
Short term impact on female sexual function of pelvic floor reconstruction with the Prolift procedure.
2009 Nov
Transvaginal mesh repair of anterior and posterior vaginal wall prolapse: a clinical and ultrasonographic study.
2010 Apr
Anatomical and functional outcomes of posterior intravaginal slingplasty for the treatment of vaginal vault or uterine prolapse: a prospective, multicenter study.
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
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
Vaginal hysterectomy at the time of transvaginal mesh placement.
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

Phase III study: 4-10 mg once daily for 14 weeks
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:31:02 GMT 2025
Edited
by admin
on Mon Mar 31 18:31:02 GMT 2025
Record UNII
XQO13W6OCH
Record Status Validated (UNII)
Record Version
  • Download
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
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PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY