ESREBOXETINE SUCCINATE

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.[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	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 38 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 8297		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: the first selective noradrenaline re-uptake inhibitor.	2000 May	11249515
Antifungal properties of selective serotonin reuptake inhibitors against Aspergillus species in vitro.	2001 Dec	11733460
Acute dystonic reaction in an elderly patient with mood disorder after titration of paroxetine: possible mechanisms and implications for clinical care.	2002 Dec	12503843
Effect of repeated treatment with reboxetine on the central alpha 1-adrenergic and dopaminergic receptors.	2002 Nov-Dec	12866714
Acute akinetic crisis with marked cognitive impairment due to Valproate treatment.	2003 Apr	12673616
Reboxetine for the treatment of patients with Cocaine Dependence Disorder.	2005 Apr	15799010
Nitrile glove permeation of benomyl.	2006 Apr	16446997
[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	16856516
One-year anatomic and quality-of-life outcomes after the Prolift procedure for treatment of posthysterectomy prolapse.	2008 Dec	18986641
Does the Prolift system cause dyspareunia?	2008 Dec	18977469
[Epidemiology and treatment for urinary incontinence and pelvic organ prolapse in women].	2008 Jul	18839620
Short-term outcome after transvaginal mesh repair of pelvic organ prolapse.	2008 Jun	18074068
A prospective study to evaluate the anatomic and functional outcome of a transobturator mesh kit (prolift anterior) for symptomatic cystocele repair.	2008 Sep-Oct	18722974
Implants in operative therapy in women with pelvic organ prolapse--two years of experience.	2009	20120436
Vaginal vault prolapse.	2009	19936123
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	19125198
Association of changes in norepinephrine and serotonin transporter expression with the long-term behavioral effects of antidepressant drugs.	2009 May	18923402
[Clinical observation on quality of life of two different operative methods of total pelvic floor reconstruction.].	2009 Nov	20079033
Laparoscopic sacrohysteropexy and myomectomy for uterine prolapse: a case report and review of the literature.	2009 Nov 3	19946516
[Prolene mesh comparing with sacrospinal fixation in the treatment of genital prolapse in women. Prospective multicentre randomized study].	2010 Apr	20518266
Permeation of herbicidal dichlobenil from a Casoron formulation through nitrile gloves.	2010 Feb	19855916
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
[Patent for medical device: from design to marketing (example of Prolift®)].	2010 Oct	20591581
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
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 `Fri Dec 15 16:32:56 GMT 2023` Edited by `admin` on `Fri Dec 15 16:32:56 GMT 2023`
Record UNII	XQO13W6OCH
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

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

(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