ESREBOXETINE SUCCINATE

Investigational

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 Search

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

Description
Sources: https://adisinsight.springer.com/drugs/800040151 | https://www.ncbi.nlm.nih.gov/pubmed/12973468 | https://www.ncbi.nlm.nih.gov/pubmed/22275142 | https://www.ncbi.nlm.nih.gov/pubmed/27230580 | https://www.ncbi.nlm.nih.gov/pubmed/20423348

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

Primary Target	Pharmacology	Condition	Potency
Sodium-dependent noradrenaline transporter 39 Target ID: P23975 Gene ID: 6530.0 Gene Symbol: SLC6A2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/27230580 \| https://www.ncbi.nlm.nih.gov/pubmed/20423348 \| https://www.ncbi.nlm.nih.gov/pubmed/18672364	Inhibitor 8504		0.08 nM [Ki]

PubMed

Title	Date	PubMed
Pharmacokinetics of reboxetine in healthy volunteers. Single oral doses, linearity and plasma protein binding.	1995 Aug	7579027
Efficacy and tolerability of reboxetine compared with imipramine in a double-blind study in patients suffering from major depressive offsodes.	1997 Apr	9169309
Reboxetine for the treatment of patients with Cocaine Dependence Disorder.	2005 Apr	15799010
[Advanced mesh implants for vaginal pelvic floor reconstruction: report of 100 prolift operations].	2007 Dec	18254441
Transvaginal repair of genital prolapse: preliminary results of a new tension-free vaginal mesh (Prolift technique)--a case series multicentric study.	2007 Jul	17131170
Pelvic arterial embolization in the setting of acute hemorrhage as a result of the anterior Prolift procedure.	2007 Jul	17021672
Fixed combinations in the management of hypertension: perspectives on lercanidipine-enalapril.	2008	19066001
Hormonal influences on cardiovascular norepinephrine transporter responses in healthy women.	2008 Apr	18259012
One-year anatomic and quality-of-life outcomes after the Prolift procedure for treatment of posthysterectomy prolapse.	2008 Dec	18986641
Vaginal repair of cystocele with anterior wall mesh via transobturator route: efficacy and complications with up to 3-year followup.	2009	19710939
The combined dexamethasone/CRH Test (DEX/CRH test) and prediction of acute treatment response in major depression.	2009	19177168
Short term impact on female sexual function of pelvic floor reconstruction with the Prolift procedure.	2009 Nov	19627464
Transvaginal mesh repair of anterior and posterior vaginal wall prolapse: a clinical and ultrasonographic study.	2010 Apr	20209502
Anatomical and functional outcomes of posterior intravaginal slingplasty for the treatment of vaginal vault or uterine prolapse: a prospective, multicenter study.	2010 Mar	20414395
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	20189287
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	20940209
Now or later...Does timing of a midurethral sling in relation to transvaginal prolapse repair affect continence outcomes at 1 year?	2010 Sep	22453509
Vaginal hysterectomy at the time of transvaginal mesh placement.	2010 Sep	22453505
Antidepressant drugs transactivate TrkB neurotrophin receptors in the adult rodent brain independently of BDNF and monoamine transporter blockade.	2011	21666748
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	21916421

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 `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

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