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
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
Urinary retention with reboxetine-fluoxetine combination in a young man.	2000 Dec	11190365
Retrovesical haematoma after anterior Prolift procedure for cystocele correction.	2007 Dec	17599235
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
Perioperative outcomes of the Prolift pelvic floor repair systems following introduction to a urogynecology teaching service.	2008 Dec	18712268
[Epidemiology and treatment for urinary incontinence and pelvic organ prolapse in women].	2008 Jul	18839620
Reutilization of the Prolift mark system for the simultaneous correction of prolapse and incontinence in patients with pelvic organ prolapse and stress urinary incontinence.	2008 Nov	18674855
[Surgical treatment of female pelvic organ prolapse at the Clinic of Obstetrics and Gynecology, Hospital of Kaunas University of Medicine].	2009	19605963
Short term impact on female sexual function of pelvic floor reconstruction with the Prolift procedure.	2009 Nov	19627464
[Prolene mesh comparing with sacrospinal fixation in the treatment of genital prolapse in women. Prospective multicentre randomized study].	2010 Apr	20518266
Midterm prospective evaluation of TVT-Secur reveals high failure rate.	2010 Jul	20434258
Mid-term results of pelvic organ prolapse repair using a transvaginal mesh: the experience in Sherbooke, Quebec.	2010 Jun	20514283
Pelvic magnetic resonance imaging for assessment of the efficacy of the Prolift system for pelvic organ prolapse.	2010 Nov	20691416
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
[Transvaginal repair of genital prolapse using the Prolift technique: a prospective study].	2010 Sep	20832035
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 18:31:03 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