ESREBOXETINE

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H23NO3
Molecular Weight	313.3908
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCOC1=C(O[C@H]([C@@H]2CNCCO2)C3=CC=CC=C3)C=CC=C1

InChI

InChIKey=CBQGYUDMJHNJBX-OALUTQOASA-N

InChI=1S/C19H23NO3/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/h3-11,18-20H,2,12-14H2,1H3/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

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
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).	2011-10-13	21916421
Antidepressant drugs transactivate TrkB neurotrophin receptors in the adult rodent brain independently of BDNF and monoamine transporter blockade.	2011	21666748
[Postoperative pain after transvaginal repair of pelvic organ prolapse with or without mesh].	2010-11	21030280
Pelvic magnetic resonance imaging for assessment of the efficacy of the Prolift system for pelvic organ prolapse.	2010-11	20691416
Reboxetine for acute treatment of major depression: systematic review and meta-analysis of published and unpublished placebo and selective serotonin reuptake inhibitor controlled trials.	2010-10-12	20940209
[Patent for medical device: from design to marketing (example of Prolift®)].	2010-10	20591581
Transurethral and suprapubic mesh resection after Prolift bladder perforation: a case report.	2010-10	20204325
Now or later...Does timing of a midurethral sling in relation to transvaginal prolapse repair affect continence outcomes at 1 year?	2010-09	22453509
Vaginal hysterectomy at the time of transvaginal mesh placement.	2010-09	22453505
[Transvaginal repair of genital prolapse using the Prolift technique: a prospective study].	2010-09	20832035
Permeation of chlorothalonil through nitrile gloves: collection solvent effects in the closed-loop permeation method.	2010-07-15	20334969
Midterm prospective evaluation of TVT-Secur reveals high failure rate.	2010-07	20434258
Mid-term results of pelvic organ prolapse repair using a transvaginal mesh: the experience in Sherbooke, Quebec.	2010-06	20514283
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?	2010-05	20189287
[Changes in the length of implanted mesh after reconstructive surgery of the anterior vaginal wall].	2010-04	20518267
[Prolene mesh comparing with sacrospinal fixation in the treatment of genital prolapse in women. Prospective multicentre randomized study].	2010-04	20518266
[Correlation between stress urinary incontinence or urgency and anterior compartment defect before and after surgical treatment].	2010-04	20518265
Transvaginal mesh repair of anterior and posterior vaginal wall prolapse: a clinical and ultrasonographic study.	2010-04	20209502
Successful management of depression with reboxetine in a patient who developed Parkinsonism related to paroxetine use.	2010-04	19074535
Anatomical and functional outcomes of posterior intravaginal slingplasty for the treatment of vaginal vault or uterine prolapse: a prospective, multicenter study.	2010-03	20414395
Does trocar-guided tension-free vaginal mesh (Prolift) repair provoke prolapse of the unaffected compartments?	2010-03	19902132
Permeation of herbicidal dichlobenil from a Casoron formulation through nitrile gloves.	2010-02	19855916
One-year outcome of concurrent anterior and posterior transvaginal mesh surgery for treatment of advanced urogenital prolapse: case series.	2009-11-16	20547113
Laparoscopic sacrohysteropexy and myomectomy for uterine prolapse: a case report and review of the literature.	2009-11-03	19946516
[Clinical observation on quality of life of two different operative methods of total pelvic floor reconstruction.].	2009-11	20079033
A serious complication following placement of posterior Prolift.	2009-11	19834758
Anatomic outcomes of vaginal mesh procedure (Prolift) compared with uterosacral ligament suspension and abdominal sacrocolpopexy for pelvic organ prolapse: a Fellows' Pelvic Research Network study.	2009-11	19716533
Synthetic graft use in vaginal prolapse surgery: objective and subjective outcomes.	2009-11	19714287
Short term impact on female sexual function of pelvic floor reconstruction with the Prolift procedure.	2009-11	19627464
Trocar-guided total tension-free vaginal mesh repair of post-hysterectomy vaginal vault prolapse.	2009-10	19499156
Laparoscopic apical mesh excision for deep dyspareunia caused by mesh banding in the vaginal apex.	2009-09	19127368
De novo stress incontinence and pelvic muscle symptoms after transvaginal mesh repair.	2009-07	19393596
Changes in levator ani muscle after vaginal hysterectomy and prolapse repair using the Total Prolift procedure.	2009-07	19358987
[Transvaginal repair of genital prolapse with prolift: a standardized surgery?].	2009-04	19261393
Perineal approach to vascular anatomy during transobturator cystocele repair.	2009-04	19191780
[Choice of a surgical treatment of genital prolapse in women].	2009-03-03	19248596
[Transvaginal repair of genital prolapse with Prolift: evaluation of safety and learning curve].	2009-02	19036533
Implants in operative therapy in women with pelvic organ prolapse--two years of experience.	2009	20120436
Vaginal vault prolapse.	2009	19936123
Vaginal repair of cystocele with anterior wall mesh via transobturator route: efficacy and complications with up to 3-year followup.	2009	19710939
[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
The combined dexamethasone/CRH Test (DEX/CRH test) and prediction of acute treatment response in major depression.	2009	19177168
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
Total Prolift System surgery for treatment posthysterectomy vaginal vault prolapse--do we treat both anatomy and function?	2008-12	19175040
[Clinical study on concomitant surgery for stress urinary incontinence and pelvic organ prolapse].	2008-10-15	19094645
[Occult stress incontinence identified by preoperative urodynamic study in women with severe pelvic organ prolapse].	2008-09	19013982
Fixed combinations in the management of hypertension: perspectives on lercanidipine-enalapril.	2008	19066001
Efficacy and tolerability of reboxetine compared with imipramine in a double-blind study in patients suffering from major depressive offsodes.	1997-04	9169309
Pharmacokinetics of reboxetine in healthy volunteers. Single oral doses, linearity and plasma protein binding.	1995-08	7579027

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 18:31:03 GMT 2025` Edited by `admin` on `Mon Mar 31 18:31:03 GMT 2025`
Record UNII	L8S50ZY490
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ESREBOXETINE

Official Name

English

(S,S)-REBOXETINE

Preferred Name

English

ESREBOXETINE [USAN]

Common Name

English

(+)-(2S)-2-((S)-(2-ETHOXYPHENOXY)PHENYLMETHYL)MORPHOLINE

Systematic Name

English

esreboxetine [INN]

Common Name

English

MORPHOLINE, 2-((S)-(2-ETHOXYPHENOXY)PHENYLMETHYL)-, (2S)-

Systematic Name

English

SS-RBX

Common Name

English

[S,S]-RBX

Code

English

S,S-REBOXETINE

Common Name

English

Esreboxetine [WHO-DD]

Common Name

English

Code System Code Type Description

PUBCHEM

65856