REBOXETINE

Details

Stereochemistry	RACEMIC
Molecular Formula	C19H23NO3
Molecular Weight	313.3908
Optical Activity	( + / - )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]1(CNCCO1)[C@H](OC2=CC=CC=C2OCC)C3=CC=CC=C3

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

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Description
Sources: http://secure.healthlinks.net.au/content/pf/retriever.cfm?product=pfcedrot11012
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Noradrenalin reuptake 2 Target ID: Noradrenalin reuptake Sources: https://www.ncbi.nlm.nih.gov/pubmed/10752718	Inhibitor 8297		8.0 nM [IC50]
Serotonin reuptake 2 Target ID: Serotonin reuptake Sources: https://www.ncbi.nlm.nih.gov/pubmed/10752718	Inhibitor 8297		1.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Major depressive disorder 173 Sources: https://www.drugs.com/uk/reboxetine-4mg-tablets-leaflet.html	Primary		Approved 8429	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

Title	Date	PubMed
Pharmacokinetics of reboxetine in healthy volunteers. Single oral doses, linearity and plasma protein binding.	1995 Aug	7579027
Reboxetine versus imipramine in the treatment of elderly patients with depressive disorders: a double-blind randomised trial.	1999 Oct	10628889
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
Residual symptoms in depressed patients after treatment with fluoxetine or reboxetine.	2005 Nov	16420078
Influences of norepinephrine transporter function on the distribution of sympathetic activity in humans.	2006 Jul	16717144
[Synthetic meshes for transvaginal surgical cure of genital prolapse: evaluation in 2005].	2006 Sep	16940912
[The prosthetic kits in the prolapse surgery: is it a gadget?].	2007 May	17400401
A case of non-SIADH-induced hyponatremia in depression after treatment with reboxetine.	2009	17965988
[Transvaginal repair of genital prolapse with prolift: a standardized surgery?].	2009 Apr	19261393
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
Association of changes in norepinephrine and serotonin transporter expression with the long-term behavioral effects of antidepressant drugs.	2009 May	18923402
[Clinical observation on quality of life of two different operative methods of total pelvic floor reconstruction.].	2009 Nov	20079033
Synthetic graft use in vaginal prolapse surgery: objective and subjective outcomes.	2009 Nov	19714287
Laparoscopic apical mesh excision for deep dyspareunia caused by mesh banding in the vaginal apex.	2009 Sep	19127368
[Correlation between stress urinary incontinence or urgency and anterior compartment defect before and after surgical treatment].	2010 Apr	20518265
Permeation of herbicidal dichlobenil from a Casoron formulation through nitrile gloves.	2010 Feb	19855916
Anatomical and functional outcomes of posterior intravaginal slingplasty for the treatment of vaginal vault or uterine prolapse: a prospective, multicenter study.	2010 Mar	20414395
Transurethral and suprapubic mesh resection after Prolift bladder perforation: a case report.	2010 Oct	20204325
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

Patents

Sample Use Guides

In Vivo Use Guide

8 mg a day (one 4 mg tablet twice a day). The maximum daily dose should not exceed 12 mg.

Route of Administration: Oral

In Vitro Use Guide

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.

Name

Type

Language

REBOXETINE

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

Reboxetine [WHO-DD]

Common Name

English

REBOXITINE

Common Name

English

reboxetine [INN]

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