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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
Can monoamine-based therapies be improved?
2002
[Duloxetine in the treatment of urinary incontinence in women].
2004 Aug
Preview of new drugs for overactive bladder and incontinence: darifenacin, solifenacin, trospium, and duloxetine.
2004 Oct
Serotonin and noradrenaline reuptake inhibitors in animal models of pain.
2004 Oct
Clinical experience with dual action antidepressants in different chronic pain syndromes.
2004 Oct
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
New drugs and dosage forms.
2004 Sep 1
Efficacy of duloxetine, a potent and balanced serotonergic and noradrenergic reuptake inhibitor, in inflammatory and acute pain models in rodents.
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
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 Tue Mar 06 11:01:07 UTC 2018 , Edited by admin on Tue Mar 06 11:01:07 UTC 2018
WHO-VATC QN06AX21
Created by admin on Tue Mar 06 11:01:07 UTC 2018 , Edited by admin on Tue Mar 06 11:01:07 UTC 2018
NDF-RT N0000000102
Created by admin on Tue Mar 06 11:01:07 UTC 2018 , Edited by admin on Tue Mar 06 11:01:07 UTC 2018
EMA ASSESSMENT REPORTS XERISTAR (AUTHORIZED: ANXIETY DISORDERS)
Created by admin on Tue Mar 06 11:01:07 UTC 2018 , Edited by admin on Tue Mar 06 11:01:07 UTC 2018
EMA ASSESSMENT REPORTS DULOXETINE MYLAN (AUTHORIZED: ANXIETY DISORDERS)
Created by admin on Tue Mar 06 11:01:07 UTC 2018 , Edited by admin on Tue Mar 06 11:01:07 UTC 2018
EMA ASSESSMENT REPORTS DULOXETINE LILLY (AUTHORIZED: NEURALGIA)
Created by admin on Tue Mar 06 11:01:07 UTC 2018 , Edited by admin on Tue Mar 06 11:01:07 UTC 2018
LIVERTOX 335
Created by admin on Tue Mar 06 11:01:07 UTC 2018 , Edited by admin on Tue Mar 06 11:01:07 UTC 2018
WHO-ATC N06AX21
Created by admin on Tue Mar 06 11:01:07 UTC 2018 , Edited by admin on Tue Mar 06 11:01:07 UTC 2018
EMA ASSESSMENT REPORTS DULOXETINE MYLAN (AUTHORIZED: NEURALGIA)
Created by admin on Tue Mar 06 11:01:07 UTC 2018 , Edited by admin on Tue Mar 06 11:01:07 UTC 2018
EMA ASSESSMENT REPORTS CYMBALTA (AUTHORIZED: ANXIETY DISORDERS)
Created by admin on Tue Mar 06 11:01:07 UTC 2018 , Edited by admin on Tue Mar 06 11:01:07 UTC 2018
NDF-RT N0000000109
Created by admin on Tue Mar 06 11:01:07 UTC 2018 , Edited by admin on Tue Mar 06 11:01:07 UTC 2018
Code System Code Type Description
HSDB
116539-59-4
Created by admin on Tue Mar 06 11:01:07 UTC 2018 , Edited by admin on Tue Mar 06 11:01:07 UTC 2018
PRIMARY
IUPHAR
202
Created by admin on Tue Mar 06 11:01:07 UTC 2018 , Edited by admin on Tue Mar 06 11:01:07 UTC 2018
PRIMARY
WIKIPEDIA
DULOXETINE
Created by admin on Tue Mar 06 11:01:07 UTC 2018 , Edited by admin on Tue Mar 06 11:01:07 UTC 2018
PRIMARY
INN
7012
Created by admin on Tue Mar 06 11:01:07 UTC 2018 , Edited by admin on Tue Mar 06 11:01:07 UTC 2018
PRIMARY
CAS
116539-59-4
Created by admin on Tue Mar 06 11:01:07 UTC 2018 , Edited by admin on Tue Mar 06 11:01:07 UTC 2018
PRIMARY
EPA CompTox
116539-59-4
Created by admin on Tue Mar 06 11:01:07 UTC 2018 , Edited by admin on Tue Mar 06 11:01:07 UTC 2018
PRIMARY
ChEMBL
CHEMBL1175
Created by admin on Tue Mar 06 11:01:07 UTC 2018 , Edited by admin on Tue Mar 06 11:01:07 UTC 2018
PRIMARY
MESH
C058218
Created by admin on Tue Mar 06 11:01:07 UTC 2018 , Edited by admin on Tue Mar 06 11:01:07 UTC 2018
PRIMARY
RXCUI
72625
Created by admin on Tue Mar 06 11:01:07 UTC 2018 , Edited by admin on Tue Mar 06 11:01:07 UTC 2018
PRIMARY RxNorm
NCI_THESAURUS
C65495
Created by admin on Tue Mar 06 11:01:07 UTC 2018 , Edited by admin on Tue Mar 06 11:01:07 UTC 2018
PRIMARY
PUBCHEM
60835
Created by admin on Tue Mar 06 11:01:07 UTC 2018 , Edited by admin on Tue Mar 06 11:01:07 UTC 2018
PRIMARY SWITZERF
LactMed
116539-59-4
Created by admin on Tue Mar 06 11:01:07 UTC 2018 , Edited by admin on Tue Mar 06 11:01:07 UTC 2018
PRIMARY
MERCK INDEX
M4782
Created by admin on Tue Mar 06 11:01:07 UTC 2018 , Edited by admin on Tue Mar 06 11:01:07 UTC 2018
PRIMARY Merck Index
EVMPD
SUB06424MIG
Created by admin on Tue Mar 06 11:01:07 UTC 2018 , Edited by admin on Tue Mar 06 11:01:07 UTC 2018
PRIMARY