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Details

Stereochemistry RACEMIC
Molecular Formula C19H23NO3
Molecular Weight 313.3915
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of REBOXETINE

SMILES

CCOc1ccccc1O[C@]([H])(c2ccccc2)[C@@]3([H])CNCCO3

InChI

InChIKey=CBQGYUDMJHNJBX-RTBURBONSA-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-/m1/s1

HIDE SMILES / InChI

Molecular Formula C19H23NO3
Molecular Weight 313.3915
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: description was created based on several sources, including: https://www.drugs.com/uk/reboxetine-4mg-tablets-leaflet.html | https://www.ncbi.nlm.nih.gov/pubmed/11249515 | https://www.ncbi.nlm.nih.gov/pubmed/14647527

Reboxetine is a selective noradrenergic reuptake inhibitor that acts by binding to the norepinephrine (NE) transporter and blocking reuptake of extracellular NE back into terminals. This compound has low affinity for other transporters and receptors. Reboxetine is used in acute treatment of depressive illness / major depression. Very common side effects are: difficulties to sleep (insomnia); dizziness; dry mouth; constipation; nausea (feeling sick); sweating. Based on studies conducted primarily outside the US, the FDA granted a preliminary letter of approval in 1999. However, more recent clinical studies conducted in the US and Canada, prompted by the FDA, resulted in a letter of non-approval.

Originator

Curator's Comment:: https://www.researchgate.net/publication/279568921_Potential_antidepressant_agents_-Aryloxy-benzyl_derivatives_of_ethanolamine_and_morpholine

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Noradrenalin reuptake
8.0 nM [IC50]
Target ID: Serotonin reuptake
1.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
EDRONAX

Approved Use

Reboxetine is indicated for the acute treatment of depressive illness/major depression and for maintaining the clinical improvement in patients initially responding to treatment.
PubMed

PubMed

TitleDatePubMed
Pharmacokinetics of reboxetine in healthy volunteers. Single oral doses, linearity and plasma protein binding.
1995 Aug
Efficacy and tolerability of reboxetine compared with imipramine in a double-blind study in patients suffering from major depressive offsodes.
1997 Apr
Effect of repeated treatment with reboxetine on the central alpha 1-adrenergic and dopaminergic receptors.
2002 Nov-Dec
Acute akinetic crisis with marked cognitive impairment due to Valproate treatment.
2003 Apr
The promises and pitfalls of reboxetine.
2003 Winter
Reboxetine may be helpful in the treatment of amphetamine withdrawal.
2004 Jul
Reboxetine for the treatment of patients with Cocaine Dependence Disorder.
2005 Apr
Contrasting Fos expression induced by acute reboxetine and fluoxetine in the rat forebrain: neuroanatomical substrates for the antidepressant effect.
2005 Jan
Residual symptoms in depressed patients after treatment with fluoxetine or reboxetine.
2005 Nov
Influences of norepinephrine transporter function on the distribution of sympathetic activity in humans.
2006 Jul
[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
[Synthetic meshes for transvaginal surgical cure of genital prolapse: evaluation in 2005].
2006 Sep
[Advanced mesh implants for vaginal pelvic floor reconstruction: report of 100 prolift operations].
2007 Dec
Retrovesical haematoma after anterior Prolift procedure for cystocele correction.
2007 Dec
Transvaginal repair of genital prolapse: preliminary results of a new tension-free vaginal mesh (Prolift technique)--a case series multicentric study.
2007 Jul
[Prolift system in the correction of female genital prolapse].
2007 Sep
Laparoscopic sacral colpopexy with Gynemesh as graft material--experience and results.
2007 Sep-Oct
Fixed combinations in the management of hypertension: perspectives on lercanidipine-enalapril.
2008
Complications and patient satisfaction after transobturator anterior and/or posterior tension-free vaginal polypropylene mesh for pelvic organ prolapse.
2008
Total Prolift System surgery for treatment posthysterectomy vaginal vault prolapse--do we treat both anatomy and function?
2008 Dec
[Epidemiology and treatment for urinary incontinence and pelvic organ prolapse in women].
2008 Jul
Short-term outcome after transvaginal mesh repair of pelvic organ prolapse.
2008 Jun
What is the mechanism of microalbuminuria in diabetes: a role for the glomerular endothelium?
2008 May
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
[Choice of a surgical treatment of genital prolapse in women].
2008 Nov-Dec
[Clinical study on concomitant surgery for stress urinary incontinence and pelvic organ prolapse].
2008 Oct 15
A prospective study to evaluate the anatomic and functional outcome of a transobturator mesh kit (prolift anterior) for symptomatic cystocele repair.
2008 Sep-Oct
Implants in operative therapy in women with pelvic organ prolapse--two years of experience.
2009
Psychopharmacology of ADHD in pediatrics: current advances and issues.
2009
The combined dexamethasone/CRH Test (DEX/CRH test) and prediction of acute treatment response in major depression.
2009
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
Perineal approach to vascular anatomy during transobturator cystocele repair.
2009 Apr
[Transvaginal repair of genital prolapse with Prolift: evaluation of safety and learning curve].
2009 Feb
De novo stress incontinence and pelvic muscle symptoms after transvaginal mesh repair.
2009 Jul
Changes in levator ani muscle after vaginal hysterectomy and prolapse repair using the Total Prolift procedure.
2009 Jul
[Clinical observation on quality of life of two different operative methods of total pelvic floor reconstruction.].
2009 Nov
Trocar-guided total tension-free vaginal mesh repair of post-hysterectomy vaginal vault prolapse.
2009 Oct
Laparoscopic apical mesh excision for deep dyspareunia caused by mesh banding in the vaginal apex.
2009 Sep
[Changes in the length of implanted mesh after reconstructive surgery of the anterior vaginal wall].
2010 Apr
[Prolene mesh comparing with sacrospinal fixation in the treatment of genital prolapse in women. Prospective multicentre randomized study].
2010 Apr
[Correlation between stress urinary incontinence or urgency and anterior compartment defect before and after surgical treatment].
2010 Apr
Transvaginal mesh repair of anterior and posterior vaginal wall prolapse: a clinical and ultrasonographic study.
2010 Apr
Successful management of depression with reboxetine in a patient who developed Parkinsonism related to paroxetine use.
2010 Apr
Permeation of chlorothalonil through nitrile gloves: collection solvent effects in the closed-loop permeation method.
2010 Jul 15
Mid-term results of pelvic organ prolapse repair using a transvaginal mesh: the experience in Sherbooke, Quebec.
2010 Jun
Anatomical and functional outcomes of posterior intravaginal slingplasty for the treatment of vaginal vault or uterine prolapse: a prospective, multicenter study.
2010 Mar
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
[Postoperative pain after transvaginal repair of pelvic organ prolapse with or without mesh].
2010 Nov
Transurethral and suprapubic mesh resection after Prolift bladder perforation: a case report.
2010 Oct
Antidepressant drugs transactivate TrkB neurotrophin receptors in the adult rodent brain independently of BDNF and monoamine transporter blockade.
2011
Patents

Sample Use Guides

8 mg a day (one 4 mg tablet twice a day). The maximum daily dose should not exceed 12 mg.
Route of Administration: Oral
The concentration of reboxetine that inhibited [3H]NE the uptake into rat hippocampal synaptosomes by 50% (IC50) was 8.5 nM. IC50 values for reboxetine inhibition of [3H]DA and [3H]5-HT uptake into rat striatal and hippocampal synaptosomes were 89 and 6.9 uM, respectively.
Substance Class Chemical
Created
by admin
on Sat Jun 26 15:11:07 UTC 2021
Edited
by admin
on Sat Jun 26 15:11:07 UTC 2021
Record UNII
947S0YZ36I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
REBOXETINE
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
(+/-)-(2R*)-2-((.ALPHA.R*)-.ALPHA.-(O-ETHOXYPHENOXY)BENZYL)MORPHOLINE
Common Name English
REBOXETINE [MI]
Common Name English
REBOXETINE [HSDB]
Common Name English
REBOXITINE
Common Name English
REBOXETINE [INN]
Common Name English
REBOXETINE [WHO-DD]
Common Name English
MORPHOLINE, 2-((R)-(2-ETHOXYPHENOXY)PHENYLMETHYL)-, (2R)-REL-
Common Name English
REBOXETINE [VANDF]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 656118
Created by admin on Sat Jun 26 15:11:08 UTC 2021 , Edited by admin on Sat Jun 26 15:11:08 UTC 2021
WHO-ATC N06AX18
Created by admin on Sat Jun 26 15:11:08 UTC 2021 , Edited by admin on Sat Jun 26 15:11:08 UTC 2021
WHO-VATC QN06AX18
Created by admin on Sat Jun 26 15:11:08 UTC 2021 , Edited by admin on Sat Jun 26 15:11:08 UTC 2021
NCI_THESAURUS C265
Created by admin on Sat Jun 26 15:11:08 UTC 2021 , Edited by admin on Sat Jun 26 15:11:08 UTC 2021
Code System Code Type Description
EPA CompTox
71620-89-8
Created by admin on Sat Jun 26 15:11:08 UTC 2021 , Edited by admin on Sat Jun 26 15:11:08 UTC 2021
PRIMARY
INN
5858
Created by admin on Sat Jun 26 15:11:08 UTC 2021 , Edited by admin on Sat Jun 26 15:11:08 UTC 2021
PRIMARY
PUBCHEM
127151
Created by admin on Sat Jun 26 15:11:08 UTC 2021 , Edited by admin on Sat Jun 26 15:11:08 UTC 2021
PRIMARY
DRUG BANK
DB00234
Created by admin on Sat Jun 26 15:11:08 UTC 2021 , Edited by admin on Sat Jun 26 15:11:08 UTC 2021
PRIMARY
WIKIPEDIA
REBOXETINE
Created by admin on Sat Jun 26 15:11:08 UTC 2021 , Edited by admin on Sat Jun 26 15:11:08 UTC 2021
PRIMARY
MERCK INDEX
M9514
Created by admin on Sat Jun 26 15:11:08 UTC 2021 , Edited by admin on Sat Jun 26 15:11:08 UTC 2021
PRIMARY Merck Index
ChEMBL
CHEMBL14370
Created by admin on Sat Jun 26 15:11:08 UTC 2021 , Edited by admin on Sat Jun 26 15:11:08 UTC 2021
PRIMARY
RXCUI
60842
Created by admin on Sat Jun 26 15:11:08 UTC 2021 , Edited by admin on Sat Jun 26 15:11:08 UTC 2021
PRIMARY RxNorm
EVMPD
SUB15112MIG
Created by admin on Sat Jun 26 15:11:08 UTC 2021 , Edited by admin on Sat Jun 26 15:11:08 UTC 2021
PRIMARY
MESH
C074679
Created by admin on Sat Jun 26 15:11:08 UTC 2021 , Edited by admin on Sat Jun 26 15:11:08 UTC 2021
PRIMARY
NCI_THESAURUS
C72838
Created by admin on Sat Jun 26 15:11:08 UTC 2021 , Edited by admin on Sat Jun 26 15:11:08 UTC 2021
PRIMARY
CAS
98769-81-4
Created by admin on Sat Jun 26 15:11:08 UTC 2021 , Edited by admin on Sat Jun 26 15:11:08 UTC 2021
SUPERSEDED
IUPHAR
4808
Created by admin on Sat Jun 26 15:11:08 UTC 2021 , Edited by admin on Sat Jun 26 15:11:08 UTC 2021
PRIMARY
CAS
71620-89-8
Created by admin on Sat Jun 26 15:11:08 UTC 2021 , Edited by admin on Sat Jun 26 15:11:08 UTC 2021
PRIMARY
FDA UNII
947S0YZ36I
Created by admin on Sat Jun 26 15:11:08 UTC 2021 , Edited by admin on Sat Jun 26 15:11:08 UTC 2021
PRIMARY
DRUG CENTRAL
2361
Created by admin on Sat Jun 26 15:11:08 UTC 2021 , Edited by admin on Sat Jun 26 15:11:08 UTC 2021
PRIMARY
LACTMED
Reboxetine
Created by admin on Sat Jun 26 15:11:08 UTC 2021 , Edited by admin on Sat Jun 26 15:11:08 UTC 2021
PRIMARY
HSDB
7701
Created by admin on Sat Jun 26 15:11:08 UTC 2021 , Edited by admin on Sat Jun 26 15:11:08 UTC 2021
PRIMARY
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