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Namespace Prefixes

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Statements

Subject Item: n2:DB01175
rdf:type: n5:Drug
n5:description: Escitalopram, the S-enantiomer of citalopram, belongs to a class of antidepressant agents known as selective serotonin-reuptake inhibitors (SSRIs). Despite distinct structural differences between compounds in this class, SSRIs possess similar pharmacological activity. As with other antidepressant agents, several weeks of therapy may be required before a clinical effect is seen. SSRIs are potent inhibitors of neuronal serotonin reuptake. They have little to no effect on norepinephrine or dopamine reuptake and do not antagonize α- or β-adrenergic, dopamine D2 or histamine H1 receptors. During acute use, SSRIs block serotonin reuptake and increase serotonin stimulation of somatodendritic 5-HT1A and terminal autoreceptors. Chronic use leads to desensitization of somatodendritic 5-HT1A and terminal autoreceptors. The overall clinical effect of increased mood and decreased anxiety is thought to be due to adaptive changes in neuronal function that leads to enhanced serotonergic neurotransmission. Side effects include dry mouth, nausea, dizziness, drowsiness, sexual dysfunction and headache. Side effects generally occur within the first two weeks of therapy and are usually less severe and frequent than those observed with tricyclic antidepressants. Escitalopram may be used to treat major depressive disorder (MDD) and generalized anxiety disorder (GAD).
n5:dosage: n26:271B4F08-363D-11E5-9242-09173F13E4C5 n26:271B4F09-363D-11E5-9242-09173F13E4C5 n26:271B4F0A-363D-11E5-9242-09173F13E4C5 n26:271B4F0B-363D-11E5-9242-09173F13E4C5 n26:271B4F06-363D-11E5-9242-09173F13E4C5 n26:271B4F07-363D-11E5-9242-09173F13E4C5 n26:271B4F0C-363D-11E5-9242-09173F13E4C5 n26:271B4F0D-363D-11E5-9242-09173F13E4C5 n26:271B4F0E-363D-11E5-9242-09173F13E4C5
n5:generalReferences: # Moore N, Verdoux H, Fantino B: Prospective, multicentre, randomized, double-blind study of the efficacy of escitalopram versus citalopram in outpatient treatment of major depressive disorder. Int Clin Psychopharmacol. 2005 May;20(3):131-7. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/15812262 # Boulenger JP, Huusom AK, Florea I, Baekdal T, Sarchiapone M: A comparative study of the efficacy of long-term treatment with escitalopram and paroxetine in severely depressed patients. Curr Med Res Opin. 2006 Jul;22(7):1331-41. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/16834832 # Bielski RJ, Ventura D, Chang CC: A double-blind comparison of escitalopram and venlafaxine extended release in the treatment of major depressive disorder. J Clin Psychiatry. 2004 Sep;65(9):1190-6. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/15367045 # Nierenberg AA, Greist JH, Mallinckrodt CH, Prakash A, Sambunaris A, Tollefson GD, Wohlreich MM: Duloxetine versus escitalopram and placebo in the treatment of patients with major depressive disorder: onset of antidepressant action, a non-inferiority study. Curr Med Res Opin. 2007 Feb;23(2):401-16. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/17288694 # Chen F, Larsen MB, Sanchez C, Wiborg O: The S-enantiomer of R,S-citalopram, increases inhibitor binding to the human serotonin transporter by an allosteric mechanism. Comparison with other serotonin transporter inhibitors. Eur Neuropsychopharmacol. 2005 Mar;15(2):193-8. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/15695064
n5:group: investigational approved
n5:halfLife: 27-32 hours
n5:indication: Labeled indications include major depressive disorder (MDD) and generalized anxiety disorder (GAD). Unlabeled indications include treatment of mild dementia-associated agitation in nonpsychotic patients.
owl:sameAs: n18:DB01175 n30:DB01175
dcterms:title: Escitalopram
adms:identifier: n11:129277 n12:DB01175 n13:36791 n14:PA10074 n15:146570 n16:0456-2005-01 n19:46507040 n27:Escitalopram
n5:mechanismOfAction: The antidepressant, antiobsessive-compulsive, and antibulimic actions of escitalopram are presumed to be linked to its inhibition of CNS neuronal uptake of serotonin. Escitalopram blocks the reuptake of serotonin at the serotonin reuptake pump of the neuronal membrane, enhancing the actions of serotonin on 5HT1A autoreceptors. SSRIs bind with significantly less affinity to histamine, acetylcholine, and norepinephrine receptors than tricyclic antidepressant drugs.
n5:packager: n6:271B4EED-363D-11E5-9242-09173F13E4C5 n6:271B4EEE-363D-11E5-9242-09173F13E4C5 n6:271B4EEC-363D-11E5-9242-09173F13E4C5 n6:271B4EFC-363D-11E5-9242-09173F13E4C5 n6:271B4EFD-363D-11E5-9242-09173F13E4C5 n6:271B4EFA-363D-11E5-9242-09173F13E4C5 n6:271B4EFB-363D-11E5-9242-09173F13E4C5 n6:271B4EF8-363D-11E5-9242-09173F13E4C5 n6:271B4EF9-363D-11E5-9242-09173F13E4C5 n6:271B4EF6-363D-11E5-9242-09173F13E4C5 n6:271B4EF7-363D-11E5-9242-09173F13E4C5 n6:271B4EF4-363D-11E5-9242-09173F13E4C5 n6:271B4EF5-363D-11E5-9242-09173F13E4C5 n6:271B4EF2-363D-11E5-9242-09173F13E4C5 n6:271B4EF3-363D-11E5-9242-09173F13E4C5 n6:271B4EF0-363D-11E5-9242-09173F13E4C5 n6:271B4EF1-363D-11E5-9242-09173F13E4C5 n6:271B4EEF-363D-11E5-9242-09173F13E4C5 n6:271B4F00-363D-11E5-9242-09173F13E4C5 n6:271B4F01-363D-11E5-9242-09173F13E4C5 n6:271B4EFE-363D-11E5-9242-09173F13E4C5 n6:271B4EFF-363D-11E5-9242-09173F13E4C5
n5:patent: n23:RE34712 n23:6916941 n23:1339452 n23:2373757
n5:routeOfElimination: Following oral administrations of escitalopram, the fraction of drug recovered in the urine as escitalopram and S-demethylcitalopram (S-DCT) is about 8% and 10%, respectively. The oral clearance of escitalopram is 600 mL/min, with approximately 7% of that due to renal clearance. Escitalopram is metabolized to S-DCT and S-didemethylcitalopram (S-DDCT).
n5:synonym: Esertia S-(+)-Citalopram Escitalopramum (S)-Citalopram S(+)-Citalopram Escitalopram Oxalate (+)-Citalopram
n5:toxicity: Signs of overdose include convulsions, coma, dizziness, hypotension, insomnia, nausea, vomiting, sinus tachycardia, somnolence, and ECG changes (including QT prolongation).
n5:volumeOfDistribution: * 12 L/kg
n8:hasAHFSCode: n24:28-16-04-20
n5:foodInteraction: Take without regard to meals.
n5:proteinBinding: ~56%
n5:synthesisReference: Robert Dancer, "Escitalopram hydrobromide and a method for the preparation thereof." U.S. Patent US20040167209, issued August 26, 2004.
n3:hasConcept: n4:M0406596
foaf:page: n21:lex1642.shtml n22:lexapro.htm n29:escitalopram.html
n5:IUPAC-Name: n7:271B4F13-363D-11E5-9242-09173F13E4C5
n5:InChI: n7:271B4F19-363D-11E5-9242-09173F13E4C5
n5:Molecular-Formula: n7:271B4F18-363D-11E5-9242-09173F13E4C5
n5:Molecular-Weight: n7:271B4F15-363D-11E5-9242-09173F13E4C5
n5:Monoisotopic-Weight: n7:271B4F16-363D-11E5-9242-09173F13E4C5
n5:SMILES: n7:271B4F17-363D-11E5-9242-09173F13E4C5
n5:Water-Solubility: n7:271B4F11-363D-11E5-9242-09173F13E4C5
n5:logP: n7:271B4F12-363D-11E5-9242-09173F13E4C5 n7:271B4F0F-363D-11E5-9242-09173F13E4C5 n7:271B4F28-363D-11E5-9242-09173F13E4C5
n5:logS: n7:271B4F10-363D-11E5-9242-09173F13E4C5
n8:hasATCCode: n9:N06AB10
n5:H-Bond-Acceptor-Count: n7:271B4F1F-363D-11E5-9242-09173F13E4C5
n5:H-Bond-Donor-Count: n7:271B4F20-363D-11E5-9242-09173F13E4C5
n5:InChIKey: n7:271B4F1A-363D-11E5-9242-09173F13E4C5
n5:Polar-Surface-Area--PSA-: n7:271B4F1B-363D-11E5-9242-09173F13E4C5
n5:Polarizability: n7:271B4F1D-363D-11E5-9242-09173F13E4C5
n5:Refractivity: n7:271B4F1C-363D-11E5-9242-09173F13E4C5
n5:Rotatable-Bond-Count: n7:271B4F1E-363D-11E5-9242-09173F13E4C5
n5:absorption: The absolute bioavailability of citalopram is about 80% relative to an intravenous dose.
n5:affectedOrganism: Humans and other mammals
n5:casRegistryNumber: 128196-01-0
n5:category
n5:clearance: * oral cl=600 mL/min [Following oral administrations]
n5:containedIn: n28:271B4F05-363D-11E5-9242-09173F13E4C5 n28:271B4F03-363D-11E5-9242-09173F13E4C5 n28:271B4F04-363D-11E5-9242-09173F13E4C5 n28:271B4F02-363D-11E5-9242-09173F13E4C5
n5:Bioavailability: n7:271B4F24-363D-11E5-9242-09173F13E4C5
n5:Ghose-Filter: n7:271B4F26-363D-11E5-9242-09173F13E4C5
n5:MDDR-Like-Rule: n7:271B4F27-363D-11E5-9242-09173F13E4C5
n5:Number-of-Rings: n7:271B4F23-363D-11E5-9242-09173F13E4C5
n5:Physiological-Charge: n7:271B4F22-363D-11E5-9242-09173F13E4C5
n5:Rule-of-Five: n7:271B4F25-363D-11E5-9242-09173F13E4C5
n5:Traditional-IUPAC-Name: n7:271B4F14-363D-11E5-9242-09173F13E4C5
n5:pKa--strongest-basic-: n7:271B4F21-363D-11E5-9242-09173F13E4C5