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

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
Urinary retention with reboxetine-fluoxetine combination in a young man.	2000 Dec	11190365
Cocaine and amphetamine increase extracellular dopamine in the nucleus accumbens of mice lacking the dopamine transporter gene.	2001 May 1	11312315
Norepinephrine-deficient mice lack responses to antidepressant drugs, including selective serotonin reuptake inhibitors.	2004 May 25	15148402
Lercanidipine in hypertension.	2005	17319103
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
[Synthetic meshes for transvaginal surgical cure of genital prolapse: evaluation in 2005].	2006 Sep	16940912
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
[The prosthetic kits in the prolapse surgery: is it a gadget?].	2007 May	17400401
[Prolift system in the correction of female genital prolapse].	2007 Sep	18020209
Total Prolift System surgery for treatment posthysterectomy vaginal vault prolapse--do we treat both anatomy and function?	2008 Dec	19175040
One-year anatomic and quality-of-life outcomes after the Prolift procedure for treatment of posthysterectomy prolapse.	2008 Dec	18986641
[Clinical study on concomitant surgery for stress urinary incontinence and pelvic organ prolapse].	2008 Oct 15	19094645
Implants in operative therapy in women with pelvic organ prolapse--two years of experience.	2009	20120436
Vaginal vault prolapse.	2009	19936123
[Surgical treatment of female pelvic organ prolapse at the Clinic of Obstetrics and Gynecology, Hospital of Kaunas University of Medicine].	2009	19605963
Psychopharmacology of ADHD in pediatrics: current advances and issues.	2009	19557112
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
De novo stress incontinence and pelvic muscle symptoms after transvaginal mesh repair.	2009 Jul	19393596
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
[Postoperative pain after transvaginal repair of pelvic organ prolapse with or without mesh].	2010 Nov	21030280
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
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

Patents

Sample Use Guides

In Vivo Use Guide

Phase III study: 4-10 mg once daily for 14 weeks

Route of Administration: Oral

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