Duloxetine

Title: Duloxetine
CAS Registry Number: 116539-59-4
CAS Name: (gS)-N-Methyl-g-(1-naphthalenyloxy)-2-thiophenepropanamine
Additional Names: (+)-(S)-N-methyl-g-(1-naphthyloxy)-2-thiophenepropylamine; (+)-N-methyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine
Manufacturers' Codes: LY-248686
Molecular Formula: C18H19NOS
Molecular Weight: 297.41
Percent Composition: C 72.69%, H 6.44%, N 4.71%, O 5.38%, S 10.78%
Literature References: Dual serotonin and norepinephrine reuptake inhibitor (SNRI). Prepn: D. W. Robertson et al., EP 273658; eidem, US 5023269 (1988, 1991 both to Lilly); and abs config: J. Deeter et al., Tetrahedron Lett. 31, 7101 (1990). Improved process: R. A. Berglund, US 5362886 (1994 to Lilly). Pharmacology: D. T. Wong et al., Neuropsychopharmacology 8, 23 (1993). Neurochemical effects in vivo: R. W. Fuller et al., J. Pharmacol. Exp. Ther. 269, 132 (1994). Determn of chiral purity: E. C. Rickard, R. J. Bopp, J. Chromatogr. A 680, 609 (1994). Clinical pharmacokinetics: A. Sharma et al., J. Clin. Pharmacol. 40, 161 (2000). Clinical trial in stress incontinence: P. A. Norton et al., Am. J. Obstet. Gynecol. 187, 40 (2002); in depression: M. J. Detke et al., J. Psychiatr. Res. 36, 383 (2002).
Derivative Type: Hydrochloride
CAS Registry Number: 136434-34-9
Trademarks: Ariclaim (Lilly); Cymbalta (Lilly); Yentreve (Lilly)
Molecular Formula: C18H19NOS.HCl
Molecular Weight: 333.88
Percent Composition: C 64.75%, H 6.04%, N 4.20%, O 4.79%, S 9.60%, Cl 10.62%
Properties: White solid. pKa in DMF-water (66:34): 9.6.
pKa: pKa in DMF-water (66:34): 9.6
Therap-Cat: Antidepressant; in treatment of stress urinary incontinence.
Keywords: Antidepressant; Serotonin Noradrenaline Reuptake Inhibitor (SNRI).
DuPHOS Durapatite Durene Durohydroquinone Duroquinone

Duloxetine
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Systematic (IUPAC) name
(+)-(S)-N-Methyl-3-(naphthalen-1-yloxy)-3-(thiophen-2-yl)propan-1-amine
Clinical data
Trade names Cymbalta
AHFS/Drugs.com monograph
MedlinePlus a604030
Licence data EMA:Link, US FDA:link
Pregnancy cat. C (US)
Legal status -only (US)
Routes Oral
Pharmacokinetic data
Bioavailability ~ 50% (32% to 80%)
Protein binding ~ 95%
Metabolism Liver, two P450 isozymes, CYP2D6 and CYP1A2
Half-life 12.1 hours
Excretion 70% in urine, 20% in feces
Identifiers
CAS number 116539-59-4 N (free base)
136434-34-9 (hydrochloride)
ATC code N06AX21
PubChem CID 60835
IUPHAR ligand 202
DrugBank DB00476
ChemSpider 54822 YesY
UNII O5TNM5N07U YesY
KEGG D07880 YesY
ChEBI CHEBI:36795 YesY
ChEMBL CHEMBL1175 YesY
Chemical data
Formula C18H19NOS 
Mol. mass 297.41456 g/mol
 N (what is this?)  (verify)

Duloxetine (sold under the brand names Cymbalta, Ariclaim, Xeristar, Yentreve, Duzela, Dulane) is a serotonin-norepinephrine reuptake inhibitor (SNRI) manufactured and marketed by Eli Lilly. It is prescribed for major depressive disorder and generalized anxiety disorder (GAD). Duloxetine also has approval for use in osteoarthiritis and musculoskeletal pain. Duloxetine failed the US approval for stress urinary incontinence amidst concerns over liver toxicity and suicidal events; however, it was approved for this indication in Europe, where it is recommended as an add-on medication in stress urinary incontinence instead of surgery.[1] It can also relieve the symptoms of painful peripheral neuropathy, particularly diabetic neuropathy,[2][3] and it is used to control the symptoms of fibromyalgia.