U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Fixed combinations in the management of hypertension: perspectives on lercanidipine-enalapril.
2008
Total Prolift System surgery for treatment posthysterectomy vaginal vault prolapse--do we treat both anatomy and function?
2008 Dec
[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
[Occult stress incontinence identified by preoperative urodynamic study in women with severe pelvic organ prolapse].
2008 Sep
Implants in operative therapy in women with pelvic organ prolapse--two years of experience.
2009
Vaginal vault prolapse.
2009
Vaginal repair of cystocele with anterior wall mesh via transobturator route: efficacy and complications with up to 3-year followup.
2009
[Surgical treatment of female pelvic organ prolapse at the Clinic of Obstetrics and Gynecology, Hospital of Kaunas University of Medicine].
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
[Transvaginal repair of genital prolapse with prolift: a standardized surgery?].
2009 Apr
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
A serious complication following placement of posterior Prolift.
2009 Nov
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 Nov
Synthetic graft use in vaginal prolapse surgery: objective and subjective outcomes.
2009 Nov
Short term impact on female sexual function of pelvic floor reconstruction with the Prolift procedure.
2009 Nov
Laparoscopic sacrohysteropexy and myomectomy for uterine prolapse: a case report and review of the literature.
2009 Nov 3
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 herbicidal dichlobenil from a Casoron formulation through nitrile gloves.
2010 Feb
Midterm prospective evaluation of TVT-Secur reveals high failure rate.
2010 Jul
Permeation of chlorothalonil through nitrile gloves: collection solvent effects in the closed-loop permeation method.
2010 Jul 15
One-year outcome of concurrent anterior and posterior transvaginal mesh surgery for treatment of advanced urogenital prolapse: case series.
2010 Jul-Aug
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
Does trocar-guided tension-free vaginal mesh (Prolift) repair provoke prolapse of the unaffected compartments?
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
Pelvic magnetic resonance imaging for assessment of the efficacy of the Prolift system for pelvic organ prolapse.
2010 Nov
[Patent for medical device: from design to marketing (example of Prolift®)].
2010 Oct
Transurethral and suprapubic mesh resection after Prolift bladder perforation: a case report.
2010 Oct
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
Now or later...Does timing of a midurethral sling in relation to transvaginal prolapse repair affect continence outcomes at 1 year?
2010 Sep
Vaginal hysterectomy at the time of transvaginal mesh placement.
2010 Sep
[Transvaginal repair of genital prolapse using the Prolift technique: a prospective study].
2010 Sep
Antidepressant drugs transactivate TrkB neurotrophin receptors in the adult rodent brain independently of BDNF and monoamine transporter blockade.
2011
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
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
Related Record Type Details
METABOLIC ENZYME -> INHIBITOR
IC50
METABOLIC ENZYME -> SUBSTRATE
MAJOR
METABOLIC ENZYME -> INHIBITOR
IC50
SALT/SOLVATE -> PARENT
Related Record Type Details
METABOLITE -> PARENT
IN VITRO
METABOLITE -> PARENT
IN VITRO
METABOLITE -> PARENT
IN VITRO
METABOLITE -> PARENT
IN VITRO
METABOLITE -> PARENT
IN VITRO
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC