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
Efficacy and tolerability of reboxetine compared with imipramine in a double-blind study in patients suffering from major depressive offsodes.	1997 Apr	9169309
Reversal of tetrabenazine induced depression by selective noradrenaline (norepinephrine) reuptake inhibition.	1999 Oct	10610387
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
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
[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	16856516
Retrovesical haematoma after anterior Prolift procedure for cystocele correction.	2007 Dec	17599235
Complications and patient satisfaction after transobturator anterior and/or posterior tension-free vaginal polypropylene mesh for pelvic organ prolapse.	2008	18720040
[Epidemiology and treatment for urinary incontinence and pelvic organ prolapse in women].	2008 Jul	18839620
A prospective study to evaluate the anatomic and functional outcome of a transobturator mesh kit (prolift anterior) for symptomatic cystocele repair.	2008 Sep-Oct	18722974
Vaginal vault prolapse.	2009	19936123
A case of non-SIADH-induced hyponatremia in depression after treatment with reboxetine.	2009	17965988
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	19716533
Synthetic graft use in vaginal prolapse surgery: objective and subjective outcomes.	2009 Nov	19714287
Short term impact on female sexual function of pelvic floor reconstruction with the Prolift procedure.	2009 Nov	19627464
Permeation of herbicidal dichlobenil from a Casoron formulation through nitrile gloves.	2010 Feb	19855916
Does trocar-guided tension-free vaginal mesh (Prolift) repair provoke prolapse of the unaffected compartments?	2010 Mar	19902132
[Postoperative pain after transvaginal repair of pelvic organ prolapse with or without mesh].	2010 Nov	21030280
Transurethral and suprapubic mesh resection after Prolift bladder perforation: a case report.	2010 Oct	20204325
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

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