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Namespace Prefixes

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Statements

Subject Item
n2:DB00476
rdf:type
n5:Drug
n5:description
Duloxetine (brand names Cymbalta, Yentreve, and in parts of Europe, Xeristar or Ariclaim) is a drug which primarily targets major depressive disorder (MDD), generalized anxiety disorder (GAD), pain related to diabetic peripheral neuropathy and in some countries stress urinary incontinence (SUI). 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.
n5:dosage
n18:271B59CF-363D-11E5-9242-09173F13E4C5 n18:271B59D4-363D-11E5-9242-09173F13E4C5 n18:271B59D5-363D-11E5-9242-09173F13E4C5 n18:271B59D6-363D-11E5-9242-09173F13E4C5 n18:271B59D0-363D-11E5-9242-09173F13E4C5 n18:271B59D1-363D-11E5-9242-09173F13E4C5 n18:271B59D2-363D-11E5-9242-09173F13E4C5 n18:271B59D3-363D-11E5-9242-09173F13E4C5
n5:generalReferences
# Turcotte JE, Debonnel G, de Montigny C, Hebert C, Blier P: Assessment of the serotonin and norepinephrine reuptake blocking properties of duloxetine in healthy subjects. Neuropsychopharmacology. 2001 May;24(5):511-21. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/11282251 # Anttila S, Leinonen E: Duloxetine Eli Lilly. Curr Opin Investig Drugs. 2002 Aug;3(8):1217-21. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/12211418 # Karpa KD, Cavanaugh JE, Lakoski JM: Duloxetine pharmacology: profile of a dual monoamine modulator. CNS Drug Rev. 2002 Winter;8(4):361-76. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/12481192 # van Groeningen CJ, Peters GJ, Pinedo HM: Lack of effectiveness of combined 5-fluorouracil and leucovorin in patients with 5-fluorouracil-resistant advanced colorectal cancer. Eur J Cancer Clin Oncol. 1989 Jan;25(1):45-9. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/2784100 # Jost W, Marsalek P: Duloxetine: mechanism of action at the lower urinary tract and Onuf's nucleus. Clin Auton Res. 2004 Aug;14(4):220-7. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/15316838 # Carter NJ, McCormack PL: Duloxetine: a review of its use in the treatment of generalized anxiety disorder. CNS Drugs. 2009;23(6):523-41. doi: 10.2165/00023210-200923060-00006. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/19480470
n5:group
approved
n5:halfLife
12 hours (range 8-17 hours)
n5:indication
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.
n5:manufacturer
n13:271B59C8-363D-11E5-9242-09173F13E4C5
owl:sameAs
n10:DB00476 n27:DB00476
dcterms:title
Duloxetine
adms:identifier
n15:Duloxetine n21:54822 n22:DB00476 n23:36795 n24:D01179 n25:54868-5215-2 n26:202 n28:202 n29:46507937 n30:PA10066 n31:60835
n5:mechanismOfAction
Duloxetine is a potent inhibitor of neuronal serotonin and norepinephrine reuptake and a less potent inhibitor of dopamine reuptake. Duloxetine has no significant affinity for dopaminergic, adrenergic, cholinergic, histaminergic, opioid, glutamate, and GABA receptors. The antidepressant and pain inhibitory actions of duloxetine are believed to be related to its potentiation of serotonergic and noradrenergic activity in the CNS. The mechanism of action of duloxetine in SUI has not been determined, but is thought to be associated with the potentiation of serotonin and norepinephrine activity in the spinal cord, which increases urethral closure forces and thereby reduces involuntary urine loss.
n5:packager
n13:271B59BC-363D-11E5-9242-09173F13E4C5 n13:271B59BD-363D-11E5-9242-09173F13E4C5 n13:271B59BA-363D-11E5-9242-09173F13E4C5 n13:271B59BB-363D-11E5-9242-09173F13E4C5 n13:271B59B9-363D-11E5-9242-09173F13E4C5 n13:271B59C6-363D-11E5-9242-09173F13E4C5 n13:271B59C7-363D-11E5-9242-09173F13E4C5 n13:271B59C4-363D-11E5-9242-09173F13E4C5 n13:271B59C5-363D-11E5-9242-09173F13E4C5 n13:271B59C2-363D-11E5-9242-09173F13E4C5 n13:271B59C3-363D-11E5-9242-09173F13E4C5 n13:271B59C0-363D-11E5-9242-09173F13E4C5 n13:271B59C1-363D-11E5-9242-09173F13E4C5 n13:271B59BE-363D-11E5-9242-09173F13E4C5 n13:271B59BF-363D-11E5-9242-09173F13E4C5 n13:271B59B4-363D-11E5-9242-09173F13E4C5 n13:271B59B7-363D-11E5-9242-09173F13E4C5 n13:271B59B8-363D-11E5-9242-09173F13E4C5 n13:271B59B5-363D-11E5-9242-09173F13E4C5 n13:271B59B6-363D-11E5-9242-09173F13E4C5
n5:patent
n8:2153856 n8:2344057 n8:5023269 n8:6596756
n5:routeOfElimination
Many additional metabolites have been identified in urine, some representing only minor pathways of elimination. Most (about 70%) of the duloxetine dose appears in the urine as metabolites of duloxetine; about 20% is excreted in the feces.
n5:synonym
(3S)-N-Methyl-3-(1-naphthyloxy)-3-(2-thienyl)propan-1-amine LY 248686
n5:toxicity
Oral, rat LD<sub>50</sub>: 491 mg/kg for males and 279 mg/kg for females. Symptoms of overdose include tremors, convulsions, reduced activity, slow pupillary response, intermittent tremors, and rigidity.
n5:volumeOfDistribution
* 1640 L
n5:foodInteraction
Take without regard to meals. People taking this product who drink large amounts of alcohol are exposed to a higher risk of liver toxicity. Food does not affect maximum levels reached, but delays it (from 6 to 10 hours) and total product exposure appears to be reduced by only 10%.
n5:proteinBinding
Protein binding is greater than 90%.
n5:salt
n5:synthesisReference
Richard A. Berglund, "Intermediate useful for the asymmetric synthesis of duloxetine." U.S. Patent US5491243, issued June, 1991.
n16:hasConcept
n17:M0162461
foaf:page
n7:cymbalta.htm n19:duloxetine-delayed-release-capsules.html
n5:IUPAC-Name
n12:271B59DB-363D-11E5-9242-09173F13E4C5
n5:InChI
n12:271B59E1-363D-11E5-9242-09173F13E4C5
n5:Molecular-Formula
n12:271B59E0-363D-11E5-9242-09173F13E4C5
n5:Molecular-Weight
n12:271B59DD-363D-11E5-9242-09173F13E4C5
n5:Monoisotopic-Weight
n12:271B59DE-363D-11E5-9242-09173F13E4C5
n5:SMILES
n12:271B59DF-363D-11E5-9242-09173F13E4C5
n5:Water-Solubility
n12:271B59D9-363D-11E5-9242-09173F13E4C5
n5:logP
n12:271B59D7-363D-11E5-9242-09173F13E4C5 n12:271B59DA-363D-11E5-9242-09173F13E4C5 n12:271B59F0-363D-11E5-9242-09173F13E4C5
n5:logS
n12:271B59D8-363D-11E5-9242-09173F13E4C5
n3:hasATCCode
n4:N06AX21
n5:H-Bond-Acceptor-Count
n12:271B59E7-363D-11E5-9242-09173F13E4C5
n5:H-Bond-Donor-Count
n12:271B59E8-363D-11E5-9242-09173F13E4C5
n5:InChIKey
n12:271B59E2-363D-11E5-9242-09173F13E4C5
n5:Polar-Surface-Area--PSA-
n12:271B59E3-363D-11E5-9242-09173F13E4C5
n5:Polarizability
n12:271B59E5-363D-11E5-9242-09173F13E4C5
n5:Refractivity
n12:271B59E4-363D-11E5-9242-09173F13E4C5
n5:Rotatable-Bond-Count
n12:271B59E6-363D-11E5-9242-09173F13E4C5
n5:absorption
Orally administered duloxetine hydrochloride is well absorbed.
n5:affectedOrganism
Humans and other mammals
n5:casRegistryNumber
136434-34-9
n5:containedIn
n11:271B59CE-363D-11E5-9242-09173F13E4C5 n11:271B59CC-363D-11E5-9242-09173F13E4C5 n11:271B59CD-363D-11E5-9242-09173F13E4C5 n11:271B59CA-363D-11E5-9242-09173F13E4C5 n11:271B59CB-363D-11E5-9242-09173F13E4C5 n11:271B59C9-363D-11E5-9242-09173F13E4C5
n5:Bioavailability
n12:271B59EC-363D-11E5-9242-09173F13E4C5
n5:Ghose-Filter
n12:271B59EE-363D-11E5-9242-09173F13E4C5
n5:MDDR-Like-Rule
n12:271B59EF-363D-11E5-9242-09173F13E4C5
n5:Number-of-Rings
n12:271B59EB-363D-11E5-9242-09173F13E4C5
n5:Physiological-Charge
n12:271B59EA-363D-11E5-9242-09173F13E4C5
n5:Rule-of-Five
n12:271B59ED-363D-11E5-9242-09173F13E4C5
n5:Traditional-IUPAC-Name
n12:271B59DC-363D-11E5-9242-09173F13E4C5
n5:pKa--strongest-basic-
n12:271B59E9-363D-11E5-9242-09173F13E4C5