Duloxetine hydrochloride

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H19NOS.ClH
Molecular Weight	333.876
Optical Activity	( + )
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=BFFSMCNJSOPUAY-LMOVPXPDSA-N

InChI=1S/C18H19NOS.ClH/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;1H/t17-;/m0./s1

HIDE SMILES / InChI

Molecular Formula	C18H19NOS
Molecular Weight	297.415
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.drugbank.ca/drugs/DB00476
Curator's Comment: Description was created based on several sources, including https://www.drugs.com/pro/cymbalta.html

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

Targets

Primary Target	Pharmacology	Potency
Serotonin transporter 183 Target ID: CHEMBL228 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25221656	Inhibitor 8504	10.4 nM [IC50]
Norepinephrine transporter 197 Target ID: CHEMBL222 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23347683	Inhibitor 8504	1.58 nM [IC50]
HERG 99 Target ID: CHEMBL240 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23666493	Inhibitor 8504	142.8 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Major depressive disorder 179 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021427s048lbl.pdf	Primary	Approved 8583	Cymbalta Approved Use Cymbalta® is indicated for the treatment of: Major Depressive Disorder Generalized Anxiety Disorder Diabetic Peripheral Neuropathy Fibromyalgia Chronic Musculoskeletal Pain Launch Date 2004
Generalized anxiety disorder 32 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021427s048lbl.pdf	Primary	Approved 8583	Cymbalta Approved Use Cymbalta® is indicated for the treatment of: Major Depressive Disorder Generalized Anxiety Disorder Diabetic Peripheral Neuropathy Fibromyalgia Chronic Musculoskeletal Pain Launch Date 2004
Fibromyalgia 90 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021427s048lbl.pdf	Palliative	Approved 8583	Cymbalta Approved Use Cymbalta® is indicated for the treatment of: Major Depressive Disorder Generalized Anxiety Disorder Diabetic Peripheral Neuropathy Fibromyalgia Chronic Musculoskeletal Pain Launch Date 2004

C_max

Value	Dose	Analyte	Population
10.44 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23678352	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:	DULOXETINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
31.82 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23678352	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:	DULOXETINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
55.88 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23678352	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	DULOXETINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
43.09 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23678352	30 mg 1 times / day multiple, oral dose: 30 mg route of administration: Oral experiment type: MULTIPLE co-administered:	DULOXETINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

AUC

Value	Dose	Analyte	Population
175.39 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23678352	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:	DULOXETINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
489.35 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23678352	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:	DULOXETINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
1073.99 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23678352	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	DULOXETINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
840.26 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23678352	30 mg 1 times / day multiple, oral dose: 30 mg route of administration: Oral experiment type: MULTIPLE co-administered:	DULOXETINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

T_1/2

Value	Dose	Analyte	Population
9.52 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23678352	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:	DULOXETINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
10.19 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23678352	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:	DULOXETINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
11.89 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23678352	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	DULOXETINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
11.39 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23678352	30 mg 1 times / day multiple, oral dose: 30 mg route of administration: Oral experiment type: MULTIPLE co-administered:	DULOXETINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
10% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021427s032s038lbl.pdf			DULOXETINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inducer 1087	inhibitor 2438 inducer 440	substrate 1388 inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP3A 227 P-gp 1741	CYP1A2 1197 CYP2C11 9 BCRP 697	CYP1A2 832 CYP2C19 329 CYP2E1 131 CYP2A6 86

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP2A6 911	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/021427_s000_Cymbalta_BioPharmr_P1.pdf#page=9 Page: 9.0	likely
CYP2C19 2141	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/021427_s000_Cymbalta_BioPharmr_P1.pdf#page=9 Page: 9.0	likely
CYP2C9 2497	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/021427_s000_Cymbalta_BioPharmr_P1.pdf#page=9 Page: 9.0	likely
CYP2E1 1146	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/021427_s000_Cymbalta_BioPharmr_P1.pdf#page=9 Page: 9.0	likely
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21427lbl.pdf#page=8 Page: 8.0	moderate	yes (co-administration study) Comment: AUC of desipramine increased 3-fold Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21427lbl.pdf#page=8 Page: 8.0
CYP1A2 2333	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/021427_s000_Cymbalta_BioPharmr_P1.pdf#page=9 Page: 9.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21427lbl.pdf#PAGE=3 Page: 3.0	no
CYP3A 317	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21427lbl.pdf#PAGE=3 Page: 3.0	no
CYP3A4 2633	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/021427_s000_Cymbalta_BioPharmr_P1.pdf#page=9 Page: 9.0	no
P-gp 1932	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/21312289/	weak [Inhibition 0.2 uM]	weak (co-administration study) Comment: concentration dependent inhibition; A six-day treatment period with DLX increased the AUC0–60, AUC0–1, and Cmax of oral administered talinolol by 11, 13, and 36%, respectively; Sources: https://pubmed.ncbi.nlm.nih.gov/21312289/

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP2C11 9	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/021427_s000_Cymbalta_BioPharmr_P1.pdf#page=4 Page: 4.0	likely
BCRP 697	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/31037729/	no
CYP1A2 1197	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21427lbl.pdf#page=8 Page: 8.0	yes	yes (co-administration study) Comment: concomitant use of duloxetine with fluvoxamine (CYP1A2 inhibitor) results in ~6-fold increase in AUC and ~2.5-fold increase in Cmax of duloxetine; Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21427lbl.pdf#page=8 Page: 8.0
CYP2D6 1388	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21427lbl.pdf#page=8 Page: 8.0	yes	yes (co-administration study) Comment: Paroxetine increased the concentration of duloxetine ~60% Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21427lbl.pdf#page=8 Page: 8.0

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/021427_s000_Cymbalta_Pharmr_P2.pdf#page=15 Page: 15.0

Sourcing

Vendor/Aggregator	ID	URL
AA Blocks	AA000CN4	https://www.aablocks.com/goods/Goods/detail?id=AA000CN4
abcr GmbH	AB457907	http://www.abcr.com/shop/en/AB457907
AEchem Scientific Corp., USA	AE1-015921	http://www.aechemsc.com/info_products/AE1-015921.php
Ambinter	Amb2383482	http://www.ambinter.com/reference/2383482
Angene	AGN-PC-0WH8CM	http://www.angenechemical.com/productshow/AGN-PC-0WH8CM.html
Anward	ANW-63714	http://www.anward.com/pro_result/50165
Aurora Fine Chemicals LLC	A13.108.273	http://online.aurorafinechemicals.com/info?ID=A13.108.273
Aurora Fine Chemicals LLC	K16.552.236	http://online.aurorafinechemicals.com/info?ID=K16.552.236
AvaChem Scientific	2477B	http://www.avachem.com/productSearch.asp?2477B
BioSynth	J-003455	https://www.biosynth.com/en/products/all-products/products/J-003455.html
BioSynth	J-523680	https://www.biosynth.com/en/products/all-products/products/J-523680.html
Boerchem	BC209438	http://www.boerchem.com/?product_35538.html
Chem Scene	CS-2885	http://www.chemscene.com/116539-59-4.html
ChemMol	30104847	http://www.chemmol.com/chemmol/30104847.html
ChemMol	44003671	http://www.chemmol.com/chemmol/44003671.html
ChemMol	44025800	http://www.chemmol.com/chemmol/44025800.html
ChemMol	49409213	http://www.chemmol.com/chemmol/49409213.html
Chemspace	CSSB00020625809	https://chem-space.com/CSSB00020625809
Chiralblock Biosciences	CB11586	http://www.chiralblock.com/products/136434-34-9.html
Coresyn	CM14423	http://www.coresyn.com/Cas136434-34-9.html
eNovation Chemicals	D543517	https://www.enovationchem.com/ProductDetails.asp?ProductID=D543517
Huateng Pharma	F94921	https://en.huatengsci.com/products/intermediates/
iChemical	EBD2816	http://www.ichemical.com/products/116539-59-4.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
Lab Network	LN00195342	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00195342
Matrix Scientific	94812	https://www.matrixscientific.com/094812.html
MedChem Express	HY-B0161	https://www.medchemexpress.com/duloxetine.html
MuseChem	I000594	https://www.musechem.com/product/I000594.html
Oakwood	225973	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=106972&ExtHyperLink=1
OChem	734	http://www.ocheminc.com/index.php?act=psearch&pid=539D594
Parchem	28799	http://www.parchem.com/chemical-supplier-distributor/Duloxetine-018799.aspx
Renno Tech	RL00632	http://www.rennotech.com/product_show.asp?id=1378
Smolecule	S526715	http://www.smolecule.com/products/s526715
Smolecule	S526716	http://www.smolecule.com/products/s526716
Synblock Inc	SB19317	http://www.synblock.com/product/116539-59-4.html
THE BioTek	bt-266662	https://www.thebiotek.com/product/inhibitors/bt-266662
THE BioTek	bt-266663	https://www.thebiotek.com/product/inhibitors/bt-266663
Vesino Industrial Co Ltd	VA11973	http://www.vsnchem.com/goto/product/22274/
Yuhao Chemical	LX2118	http://www.chemyuhao.com/116539-59-4.html

PubMed

Title	Date	PubMed
Can monoamine-based therapies be improved?	2002	15453009
Role of 5-HT receptors in treatment of overactive bladder.	2003 Aug	14566383
Physical symptoms comorbid with depression and the new antidepressant duloxetine.	2003 Dec	14682027
Innovations in pharmacotherapy for stress urinary incontinence.	2003 Dec	14676995
Duloxetine (Cymbalta), a dual inhibitor of serotonin and norepinephrine reuptake.	2003 Dec 15	14643350
The development of new antidepressants: focus on duloxetine and escitalopram.	2003 Jan-Feb	12866739
Mixed urinary incontinence symptoms: urodynamic findings, incontinence severity, and treatment response.	2003 Jul	12850610
Enhancement of antidepressant potency by a potentiator of AMPA receptors.	2003 Jun	12825836
Update on overactive bladder: pharmacologic approaches on the horizon.	2003 Oct	14499063
Common pathways of depression and pain.	2004	15315473
[Physical recovery is part of remission].	2004	15311907
Pharmacotherapy for stress urinary incontinence : present and future options.	2004	15233589
The effect of duloxetine on painful physical symptoms in depressed patients: do improvements in these symptoms result in higher remission rates?	2004 Apr	15119915
[Duloxetine in the treatment of urinary incontinence in women].	2004 Aug	15377983
Role of presynaptic alpha2-adrenoceptors in antidepressant action: recent findings from microdialysis studies.	2004 Aug	15363606
Duloxetine in the treatment of depression: a double-blind placebo-controlled comparison with paroxetine.	2004 Aug	15232330
Duloxetine vs placebo in the treatment of stress urinary incontinence: a four-continent randomized clinical trial.	2004 Feb	14764128
[Successful phase III study with serotonin-noradrenaline reuptake inhibitor. Soon a drug to control stress incontinence].	2004 Feb 12	15347056
Effect of age on the pharmacokinetics of duloxetine in women.	2004 Jan	14678340
Duloxetine's role in the treatment of depression and associated painful physical symptoms.	2004 Jul	15291696
Duloxetine versus placebo in the treatment of European and Canadian women with stress urinary incontinence.	2004 Mar	14961887
Stress incontinence: help at hand.	2004 May	15142172
[New options in the treatment of various forms of diabetic neuropathy].	2004 May 20	15373085
Preview of new drugs for overactive bladder and incontinence: darifenacin, solifenacin, trospium, and duloxetine.	2004 Oct	15461912
Serotonin and noradrenaline reuptake inhibitors in animal models of pain.	2004 Oct	15378668
Clinical experience with dual action antidepressants in different chronic pain syndromes.	2004 Oct	15378667
Duloxetine (Cymbalta): a new SNRI for depression.	2004 Oct 11	15480298
A double-blind, multicenter trial comparing duloxetine with placebo in the treatment of fibromyalgia patients with or without major depressive disorder.	2004 Sep	15457467
Balanced treatments for fibromyalgia.	2004 Sep	15457439
Pharmacological treatment of women awaiting surgery for stress urinary incontinence.	2004 Sep	15339761
New drugs and dosage forms.	2004 Sep 1	15462243
The efficacy of duloxetine: a comprehensive summary of results from MMRM and LOCF_ANCOVA in eight clinical trials.	2004 Sep 8	15355546
Efficacy of duloxetine, a potent and balanced serotonergic and noradrenergic reuptake inhibitor, in inflammatory and acute pain models in rodents.	2005 Feb	15494550
Comparative effects of duloxetine and desipramine on sleep EEG in healthy subjects.	2005 Feb	15290000

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:05:46 GMT 2025` Edited by `admin` on `Mon Mar 31 18:05:46 GMT 2025`
Record UNII	9044SC542W
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ARICLAIM

Preferred Name

English

Duloxetine hydrochloride

Official Name

English

Duloxetine hydrochloride [JAN]

Common Name

English

(S)-(+)-N-Methyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine hydrochloride

Systematic Name

English

Duloxetine (as hydrochloride)

Common Name

English

DULOXETINE LILLY

Systematic Name

English

(S)-(+)-Duloxetine hydrochloride

Common Name

English

Duloxetine hydrochloride [MART.]

Common Name

English

Duloxetine hydrochloride [WHO-DD]

Common Name

English

LY-248686 HCL

Code

English

Cymbalta

Brand Name

English

(+)-(S)-N-METHYL-.GAMMA.-(1-NAPHTHYLOXY)-2-THIOPHENEPROPYLAMINE HYDROCHLORIDE

Systematic Name

English

Duloxetine hydrochloride [EP MONOGRAPH]

Common Name

English

LY248686 HCL

Code

English

DULOXETINE BOEHRINGER INGELHEIM

Brand Name

English

2-Thiophenepropanamine, N-methyl-?-(1-naphthalenyloxy)-, hydrochloride, (S)-

Systematic Name

English

Duloxetine hydrochloride [MI]

Common Name

English

XERISTAR

Brand Name

English

DULOXETINE MYLAN

Brand Name

English

Duloxetine hydrochloride [ORANGE BOOK]

Common Name

English

Duloxetine hydrochloride [USP MONOGRAPH]

Common Name

English

Duloxetine HCL

Common Name

English

Duloxetine hydrochloride [USP-RS]

Common Name

English

NSC-759112

Code

English

Duloxetine hydrochloride [USAN]

Common Name

English

Classification Tree Code System Code

EMA ASSESSMENT REPORTS

DULOXETINE MYLAN (AUTHORIZED: DEPRESSIVE DISORDER, MAJOR)