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.[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	C19H23NO3
Molecular Weight	313.3908
Charge	0
Count

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

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

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 8228		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
Cytochrome P-450-mediated metabolism of the individual enantiomers of the antidepressant agent reboxetine in human liver microsomes.	1999 Nov	10534319
Reboxetine versus imipramine in the treatment of elderly patients with depressive disorders: a double-blind randomised trial.	1999 Oct	10628889
Reversal of tetrabenazine induced depression by selective noradrenaline (norepinephrine) reuptake inhibition.	1999 Oct	10610387
Clinical pharmacokinetics of reboxetine, a selective norepinephrine reuptake inhibitor for the treatment of patients with depression.	2000 Dec	11192474
Urinary retention with reboxetine-fluoxetine combination in a young man.	2000 Dec	11190365
Reboxetine: the first selective noradrenaline re-uptake inhibitor.	2000 May	11249515
Reboxetine: a pharmacologically potent, selective, and specific norepinephrine reuptake inhibitor.	2000 May 1	10812041
Antifungal properties of selective serotonin reuptake inhibitors against Aspergillus species in vitro.	2001 Dec	11733460
Cocaine and amphetamine increase extracellular dopamine in the nucleus accumbens of mice lacking the dopamine transporter gene.	2001 May 1	11312315
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
The promises and pitfalls of reboxetine.	2003 Winter	14647527
Reboxetine may be helpful in the treatment of amphetamine withdrawal.	2004 Jul	15207001
Norepinephrine-deficient mice lack responses to antidepressant drugs, including selective serotonin reuptake inhibitors.	2004 May 25	15148402
Reboxetine for the treatment of patients with Cocaine Dependence Disorder.	2005 Apr	15799010
Contrasting Fos expression induced by acute reboxetine and fluoxetine in the rat forebrain: neuroanatomical substrates for the antidepressant effect.	2005 Jan	15609068
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
Monotherapy with reboxetine in amphetamine withdrawal syndrome.	2006 Sep 30	16631296
[Advanced mesh implants for vaginal pelvic floor reconstruction: report of 100 prolift operations].	2007 Dec	18254441
[Prolift system in the correction of female genital prolapse].	2007 Sep	18020209
Laparoscopic sacral colpopexy with Gynemesh as graft material--experience and results.	2007 Sep-Oct	17848318
Hormonal influences on cardiovascular norepinephrine transporter responses in healthy women.	2008 Apr	18259012
Total Prolift System surgery for treatment posthysterectomy vaginal vault prolapse--do we treat both anatomy and function?	2008 Dec	19175040
Short-term outcome after transvaginal mesh repair of pelvic organ prolapse.	2008 Jun	18074068
What is the mechanism of microalbuminuria in diabetes: a role for the glomerular endothelium?	2008 May	18347777
[Choice of a surgical treatment of genital prolapse in women].	2008 Nov-Dec	19248596
Implants in operative therapy in women with pelvic organ prolapse--two years of experience.	2009	20120436
Vaginal repair of cystocele with anterior wall mesh via transobturator route: efficacy and complications with up to 3-year followup.	2009	19710939
Psychopharmacology of ADHD in pediatrics: current advances and issues.	2009	19557112
De novo stress incontinence and pelvic muscle symptoms after transvaginal mesh repair.	2009 Jul	19393596
Changes in levator ani muscle after vaginal hysterectomy and prolapse repair using the Total Prolift procedure.	2009 Jul	19358987
A serious complication following placement of posterior Prolift.	2009 Nov	19834758
Short term impact on female sexual function of pelvic floor reconstruction with the Prolift procedure.	2009 Nov	19627464
[Changes in the length of implanted mesh after reconstructive surgery of the anterior vaginal wall].	2010 Apr	20518267
[Prolene mesh comparing with sacrospinal fixation in the treatment of genital prolapse in women. Prospective multicentre randomized study].	2010 Apr	20518266
Successful management of depression with reboxetine in a patient who developed Parkinsonism related to paroxetine use.	2010 Apr	19074535
Permeation of herbicidal dichlobenil from a Casoron formulation through nitrile gloves.	2010 Feb	19855916
Permeation of chlorothalonil through nitrile gloves: collection solvent effects in the closed-loop permeation method.	2010 Jul 15	20334969
One-year outcome of concurrent anterior and posterior transvaginal mesh surgery for treatment of advanced urogenital prolapse: case series.	2010 Jul-Aug	20547113
Anatomical and functional outcomes of posterior intravaginal slingplasty for the treatment of vaginal vault or uterine prolapse: a prospective, multicenter study.	2010 Mar	20414395
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

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 `Wed Jul 05 23:58:31 UTC 2023` Edited by `admin` on `Wed Jul 05 23:58:31 UTC 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