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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H19NOS
Molecular Weight 297.415
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DULOXETINE

SMILES

CNCC[C@H](OC1=C2C=CC=CC2=CC=C1)C3=CC=CS3

InChI

InChIKey=ZEUITGRIYCTCEM-KRWDZBQOSA-N
InChI=1S/C18H19NOS/c1-19-12-11-17(18-10-5-13-21-18)20-16-9-4-7-14-6-2-3-8-15(14)16/h2-10,13,17,19H,11-12H2,1H3/t17-/m0/s1

HIDE SMILES / InChI

Description

Duloxetine (brand names Cymbalta, Yentreve, and in parts of Europe, Xeristar or Ariclaim) is indicated for the acute and maintenance treatment of major depressive disorder (MDD), as well as acute management of generalized anxiety disorder. Also used for the management of neuropathic pain associated with diabetic peripheral neuropathy, and fibromyalgia. Has been used in the management of moderate to severe stress urinary incontinence (SUI) in women. It is manufactured and marketed by Eli Lilly and Company. Duloxetine has not yet been FDA approved for stress urinary incontinence or for fibromyalgia. Duloxetine is a selective SNRI (selective serotonin-norepinephrine reuptake inhibitor). Duloxetine is a systemic drug therapy which affects the body as a whole. Known also under the code name LY248686, it is a potent dual reuptake inhibitor of serotonin (5-hydroxytryptamine, 5-HT) and norepinephrine (NE), possessing comparable affinities in binding to NE- and 5-HT transporter sites. It is a less potent inhibitor of dopamine reuptake.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Somatic symptoms, depression, and antidepressant treatment.
2002 Apr
Induction of hyperlocomotion in mice exposed to a novel environment by inhibition of serotonin reuptake. A pharmacological characterization of diverse classes of antidepressant agents.
2002 Apr
Comparison of the effects of serotonin selective, norepinephrine selective, and dual serotonin and norepinephrine reuptake inhibitors on lower urinary tract function in cats.
2002 Aug 2
Duloxetine for the treatment of major depressive disorder.
2002 Autumn
Circling behavior induced by microinjection of serotonin reuptake inhibitors in the substantia nigra.
2002 Jan-Feb
Duloxetine versus placebo in the treatment of stress urinary incontinence.
2002 Jul
Duloxetine in the treatment of major depressive disorder: a double-blind clinical trial.
2002 Mar
[18 million sick days due to depressive illnesses. New prospects in therapy of depression].
2003
Physical symptoms of depression: unmet needs in special populations.
2003
[Depression also effects the body].
2003
Role of 5-HT receptors in treatment of overactive bladder.
2003 Aug
Comparison of effects of dual transporter inhibitors on monoamine transporters and extracellular levels in rats.
2003 Dec
Dual monoamine modulation for improved treatment of major depressive disorder.
2003 Feb
Analgesic effects of antidepressants.
2003 Jan
The development of new antidepressants: focus on duloxetine and escitalopram.
2003 Jan-Feb
Neural control of the urethra and development of pharmacotherapy for stress urinary incontinence.
2003 May
Duloxetine versus placebo for the treatment of North American women with stress urinary incontinence.
2003 Oct
Newer antidepressants: review of efficacy and safety of escitalopram and duloxetine.
2004
The effect of duloxetine on painful physical symptoms in depressed patients: do improvements in these symptoms result in higher remission rates?
2004 Apr
Role of presynaptic alpha2-adrenoceptors in antidepressant action: recent findings from microdialysis studies.
2004 Aug
Duloxetine in the treatment of depression: a double-blind placebo-controlled comparison with paroxetine.
2004 Aug
Milnacipran: a comparative analysis of human monoamine uptake and transporter binding affinity.
2004 Feb 1
Targeting serotonin and norepinephrine receptors in stress urinary incontinence.
2004 Jul
New approaches in the pharmacological treatment of stress urinary incontinence.
2004 Jul
The effect of previous treatment experience and incontinence severity on the placebo response of stress urinary incontinence.
2004 Jul
Duloxetine's role in the treatment of depression and associated painful physical symptoms.
2004 Jul
Central nervous system control of the lower urinary tract: new pharmacological approaches to stress urinary incontinence in women.
2004 Jul
Role of serotonin and noradrenaline in stress urinary incontinence.
2004 Jul
Synthesis and biological activity of some known and putative duloxetine metabolites.
2004 Jul 5
Validation of a clinical algorithm to diagnose stress urinary incontinence for large studies.
2004 Jun
Duloxetine versus placebo in the treatment of European and Canadian women with stress urinary incontinence.
2004 Mar
Augmentation of milnacipran by risperidone in treatment for major depression.
2004 Mar
Efficacy of duloxetine, a potent and balanced serotonin-norepinephrine reuptake inhibitor in persistent pain models in rats.
2004 Nov
Duloxetine (Cymbalta): a new SNRI for depression.
2004 Oct 11
A double-blind, multicenter trial comparing duloxetine with placebo in the treatment of fibromyalgia patients with or without major depressive disorder.
2004 Sep
Balanced treatments for fibromyalgia.
2004 Sep
The efficacy of duloxetine: a comprehensive summary of results from MMRM and LOCF_ANCOVA in eight clinical trials.
2004 Sep 8
Efficacy of duloxetine, a potent and balanced serotonergic and noradrenergic reuptake inhibitor, in inflammatory and acute pain models in rodents.
2005 Feb
Comparative effects of duloxetine and desipramine on sleep EEG in healthy subjects.
2005 Feb
Patents

Sample Use Guides

In Vivo Use Guide
Dosage for Treatment of Major Depressive Disorder Administer CYMBALTA (Duloxetine) at a total dose of 40 mg/day (given as 20 mg twice daily) to 60 mg/day (given either once daily or as 30 mg twice daily). For some patients, it may be desirable to start at 30 mg once daily for 1 week, to allow patients to adjust to the medication before increasing to 60 mg once daily.
Route of Administration: Oral
In Vitro Use Guide
The 50% inhibitory concentration (IC50) of duloxetine for the resting and inactivated wild-type hNav1.7 Na+ channel were 22.1+/-0.4 and 1.79+/-0.10 uM, respectively. Inhibitory effects were even more pronounced when using a mammalian cell line resulting in a 34 or 59% current decrease by 10 or 30 uM duloxetine, respectively.
Name Type Language
DULOXETINE
EMA EPAR   HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
YENTREVE
Brand Name English
DULOXETINE [HSDB]
Common Name English
LY-248686
Code English
2-THIOPHENEPROPANAMINE, N-METHYL-.GAMMA.-(1-NAPHTHALENYLOXY)-, (S)-
Systematic Name English
DULOXETINE [MI]
Common Name English
DRIZALMA SPRINKLE
Brand Name English
DULOXETINE [EMA EPAR]
Common Name English
DULOXETINE [VANDF]
Common Name English
(+)-(S)-N-METHYL-.GAMMA.(1-NAPHTHYLOXY)-2-THIOPHENEPROPYLAMINE
Systematic Name English
LY248686
Code English
DULOXETINE [WHO-DD]
Common Name English
DULOXETINE [INN]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175749
Created by admin on Mon Oct 21 20:20:17 UTC 2019 , Edited by admin on Mon Oct 21 20:20:17 UTC 2019
WHO-VATC QN06AX21
Created by admin on Mon Oct 21 20:20:17 UTC 2019 , Edited by admin on Mon Oct 21 20:20:17 UTC 2019
NDF-RT N0000000102
Created by admin on Mon Oct 21 20:20:17 UTC 2019 , Edited by admin on Mon Oct 21 20:20:17 UTC 2019
EMA ASSESSMENT REPORTS XERISTAR (AUTHORIZED: ANXIETY DISORDERS)
Created by admin on Mon Oct 21 20:20:17 UTC 2019 , Edited by admin on Mon Oct 21 20:20:17 UTC 2019
NCI_THESAURUS C265
Created by admin on Mon Oct 21 20:20:17 UTC 2019 , Edited by admin on Mon Oct 21 20:20:17 UTC 2019
EMA ASSESSMENT REPORTS DULOXETINE MYLAN (AUTHORIZED: ANXIETY DISORDERS)
Created by admin on Mon Oct 21 20:20:17 UTC 2019 , Edited by admin on Mon Oct 21 20:20:17 UTC 2019
EMA ASSESSMENT REPORTS DULOXETINE LILLY (AUTHORIZED: NEURALGIA)
Created by admin on Mon Oct 21 20:20:17 UTC 2019 , Edited by admin on Mon Oct 21 20:20:17 UTC 2019
LIVERTOX 335
Created by admin on Mon Oct 21 20:20:17 UTC 2019 , Edited by admin on Mon Oct 21 20:20:17 UTC 2019
WHO-ATC N06AX21
Created by admin on Mon Oct 21 20:20:17 UTC 2019 , Edited by admin on Mon Oct 21 20:20:17 UTC 2019
EMA ASSESSMENT REPORTS DULOXETINE MYLAN (AUTHORIZED: NEURALGIA)
Created by admin on Mon Oct 21 20:20:17 UTC 2019 , Edited by admin on Mon Oct 21 20:20:17 UTC 2019
EMA ASSESSMENT REPORTS CYMBALTA (AUTHORIZED: ANXIETY DISORDERS)
Created by admin on Mon Oct 21 20:20:17 UTC 2019 , Edited by admin on Mon Oct 21 20:20:17 UTC 2019
NDF-RT N0000000109
Created by admin on Mon Oct 21 20:20:17 UTC 2019 , Edited by admin on Mon Oct 21 20:20:17 UTC 2019
Code System Code Type Description
HSDB
116539-59-4
Created by admin on Mon Oct 21 20:20:17 UTC 2019 , Edited by admin on Mon Oct 21 20:20:17 UTC 2019
PRIMARY
IUPHAR
202
Created by admin on Mon Oct 21 20:20:17 UTC 2019 , Edited by admin on Mon Oct 21 20:20:17 UTC 2019
PRIMARY
WIKIPEDIA
DULOXETINE
Created by admin on Mon Oct 21 20:20:17 UTC 2019 , Edited by admin on Mon Oct 21 20:20:17 UTC 2019
PRIMARY
INN
7012
Created by admin on Mon Oct 21 20:20:17 UTC 2019 , Edited by admin on Mon Oct 21 20:20:17 UTC 2019
PRIMARY
CAS
116539-59-4
Created by admin on Mon Oct 21 20:20:17 UTC 2019 , Edited by admin on Mon Oct 21 20:20:17 UTC 2019
PRIMARY
EPA CompTox
116539-59-4
Created by admin on Mon Oct 21 20:20:17 UTC 2019 , Edited by admin on Mon Oct 21 20:20:17 UTC 2019
PRIMARY
ChEMBL
CHEMBL1175
Created by admin on Mon Oct 21 20:20:17 UTC 2019 , Edited by admin on Mon Oct 21 20:20:17 UTC 2019
PRIMARY
MESH
C058218
Created by admin on Mon Oct 21 20:20:17 UTC 2019 , Edited by admin on Mon Oct 21 20:20:17 UTC 2019
PRIMARY
RXCUI
72625
Created by admin on Mon Oct 21 20:20:17 UTC 2019 , Edited by admin on Mon Oct 21 20:20:17 UTC 2019
PRIMARY RxNorm
NCI_THESAURUS
C65495
Created by admin on Mon Oct 21 20:20:17 UTC 2019 , Edited by admin on Mon Oct 21 20:20:17 UTC 2019
PRIMARY
PUBCHEM
60835
Created by admin on Mon Oct 21 20:20:17 UTC 2019 , Edited by admin on Mon Oct 21 20:20:17 UTC 2019
PRIMARY
LactMed
116539-59-4
Created by admin on Mon Oct 21 20:20:17 UTC 2019 , Edited by admin on Mon Oct 21 20:20:17 UTC 2019
PRIMARY
MERCK INDEX
M4782
Created by admin on Mon Oct 21 20:20:17 UTC 2019 , Edited by admin on Mon Oct 21 20:20:17 UTC 2019
PRIMARY Merck Index
EVMPD
SUB06424MIG
Created by admin on Mon Oct 21 20:20:17 UTC 2019 , Edited by admin on Mon Oct 21 20:20:17 UTC 2019
PRIMARY