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Statements

Subject Item
n2:DB01104
rdf:type
n3:Drug
n3:description
Sertraline hydrochloride 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 &alpha;- or &beta;-adrenergic, dopamine D<sub>2</sub> or histamine H<sub>1</sub> receptors. During acute use, SSRIs block serotonin reuptake and increase serotonin stimulation of somatodendritic 5-HT<sub>1A</sub> and terminal autoreceptors. Chronic use leads to desensitization of somatodendritic 5-HT<sub>1A</sub> 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 (see Toxicity section below for a more detailed listing of side effects). Compared to other agents in this class, sertraline may cause greater diarrheal and male sexual dysfunction effects. Side effects generally occur within the first two weeks of therapy and are usually less severe and frequent than those observed with tricyclic antidepressants. Sertraline may be used to treat major depressive disorder, obsessive-compulsive disorder (OCD), panic disorder, post-traumatic stress disorder (PTSD), premenstrual dysphoric disorder (PMDD) and social anxiety disorder (social phobia).
n3:dosage
n10:271B3FFD-363D-11E5-9242-09173F13E4C5 n10:271B3FFE-363D-11E5-9242-09173F13E4C5 n10:271B3FFF-363D-11E5-9242-09173F13E4C5 n10:271B4000-363D-11E5-9242-09173F13E4C5 n10:271B4005-363D-11E5-9242-09173F13E4C5 n10:271B4006-363D-11E5-9242-09173F13E4C5 n10:271B4007-363D-11E5-9242-09173F13E4C5 n10:271B4008-363D-11E5-9242-09173F13E4C5 n10:271B4001-363D-11E5-9242-09173F13E4C5 n10:271B4002-363D-11E5-9242-09173F13E4C5 n10:271B4003-363D-11E5-9242-09173F13E4C5 n10:271B4004-363D-11E5-9242-09173F13E4C5 n10:271B4009-363D-11E5-9242-09173F13E4C5 n10:271B400A-363D-11E5-9242-09173F13E4C5 n10:271B400B-363D-11E5-9242-09173F13E4C5 n10:271B400C-363D-11E5-9242-09173F13E4C5
n3:generalReferences
# Couzin J: The brains behind blockbusters. Science. 2005 Jul 29;309(5735):728. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/16051786 # Fabre LF, Abuzzahab FS, Amin M, Claghorn JL, Mendels J, Petrie WM, Dube S, Small JG: Sertraline safety and efficacy in major depression: a double-blind fixed-dose comparison with placebo. Biol Psychiatry. 1995 Nov 1;38(9):592-602. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/8573661 # Kronig MH, Apter J, Asnis G, Bystritsky A, Curtis G, Ferguson J, Landbloom R, Munjack D, Riesenberg R, Robinson D, Roy-Byrne P, Phillips K, Du Pont IJ: Placebo-controlled, multicenter study of sertraline treatment for obsessive-compulsive disorder. J Clin Psychopharmacol. 1999 Apr;19(2):172-6. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/10211919 # Brady K, Pearlstein T, Asnis GM, Baker D, Rothbaum B, Sikes CR, Farfel GM: Efficacy and safety of sertraline treatment of posttraumatic stress disorder: a randomized controlled trial. JAMA. 2000 Apr 12;283(14):1837-44. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/10770145 # Yonkers KA, Halbreich U, Freeman E, Brown C, Endicott J, Frank E, Parry B, Pearlstein T, Severino S, Stout A, Stone A, Harrison W: Symptomatic improvement of premenstrual dysphoric disorder with sertraline treatment. A randomized controlled trial. Sertraline Premenstrual Dysphoric Collaborative Study Group. JAMA. 1997 Sep 24;278(12):983-8. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/9307345 # Shelton RC: The role of sertraline in the management of depression. Clin Ther. 1994 Sep-Oct;16(5):768-82; discussion 767. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/7859236 # Murdoch D, McTavish D: Sertraline. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic potential in depression and obsessive-compulsive disorder. Drugs. 1992 Oct;44(4):604-24. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/1281075
n3:group
approved
n3:halfLife
The elimination half-life of sertraline is approximately 25-26 hours. The elimination half-life of desmethylsertraline is approximately 62-104 hours.
n3:indication
For the management of major depressive disorder, posttraumatic stress disorder, obsessive-compulsive disorder, panic disorder with or without agoraphobia, premenstrual dysphoric disorder, social phobia, premature ejaculation, and vascular headaches.
owl:sameAs
n9:DB01104 n11:DB01104
dcterms:title
Sertraline
adms:identifier
n18:61881 n19:DB01104 n20:9123 n21:D02360 n22:0049-4960-30 n23:C07246 n24:46505341 n25:PA451333 n26:68617 n31:Sertraline
n3:mechanismOfAction
The exact mechanism of action sertraline is not fully known, but the drug appears to selectively inhibit the reuptake of serotonin at the presynaptic membrane. This results in an increased synaptic concentration of serotonin in the CNS, which leads to numerous functional changes associated with enhanced serotonergic neurotransmission. It is suggested that these modifications are responsible for the antidepressant action observed during long term administration of antidepressants. It has also been hypothesized that obsessive-compulsive disorder is caused by the dysregulation of serotonin, as it is treated by sertraline, and the drug corrects this imbalance.
n3:packager
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n3:patent
n13:7067555 n13:2029065 n13:4962128
n3:routeOfElimination
Sertraline is extensively metabolized and excretion of unchanged drug in urine is a minor route of elimination.
n3:synonym
Sertraline Sertralina (+)-Sertraline CP 51974 Sertralinum (1S-cis)-1,2,3,4-Tetrahydro-4-(3,4-dichlorophenyl)-N-methyl-1-naphthalenamine cis-(+)-Sertraline (1S,4S)-Sertraline
n3:toxicity
Symptoms of toxicity include alopecia, decreased libido, diarrhea, ejaculation disorder, fatigue, insomnia, somnolence and serotonin syndrome. The most frequently observed side effects include: GI effects such as nausea, diarrhea or loose stools, dyspepsia, and dry mouth; nervous system effects such as somnolence, dizziness, insomnia, and tremor; sexual dysfunction in males (principally ejaculatory delay); and sweating.
n5:hasAHFSCode
n6:28-16-04-20
n3:foodInteraction
Avoid taking with grapefruit juice. Take with food. Avoid St.John's Wort. Avoid alcohol.
n3:proteinBinding
98% bound to serum proteins, principally to albumin and &alpha;<sub>1</sub>-acid glycoprotein
n3:salt
n3:synthesisReference
George J. Quallich, Michael T. Williams, "Process for preparing sertraline intermediates." U.S. Patent US4839104, issued February, 1977.
n28:hasConcept
n29:M0029930
foaf:page
n15:sertral.htm n30:sertraline.html
n3:IUPAC-Name
n4:271B4011-363D-11E5-9242-09173F13E4C5
n3:InChI
n4:271B4017-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n4:271B4016-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n4:271B4013-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n4:271B4014-363D-11E5-9242-09173F13E4C5
n3:SMILES
n4:271B4015-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
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n3:logP
n4:271B4028-363D-11E5-9242-09173F13E4C5 n4:271B400D-363D-11E5-9242-09173F13E4C5 n4:271B4010-363D-11E5-9242-09173F13E4C5
n3:logS
n4:271B400E-363D-11E5-9242-09173F13E4C5
n5:hasATCCode
n7:N06AB06
n3:H-Bond-Acceptor-Count
n4:271B401D-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n4:271B401E-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n4:271B4018-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n4:271B4019-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n4:271B401B-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n4:271B401A-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n4:271B401C-363D-11E5-9242-09173F13E4C5
n3:absorption
The effects of food on the bioavailability of the sertraline tablet and oral concentrate were studied in subjects administered a single dose with and without food. For the tablet, AUC was slightly increased when drug was administered with food but the Cmax was 25% greater, while the time to reach peak plasma concentration (Tmax) decreased from 8 hours post-dosing to 5.5 hours. For the oral concentrate, Tmax was slightly prolonged from 5.9 hours to 7.0 hours with food.
n3:affectedOrganism
Humans and other mammals
n3:casRegistryNumber
79617-96-2
n3:category
n3:containedIn
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n3:Bioavailability
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n3:Ghose-Filter
n4:271B4024-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n4:271B4025-363D-11E5-9242-09173F13E4C5
n3:Melting-Point
n4:271B4027-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n4:271B4021-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n4:271B4020-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n4:271B4023-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n4:271B4012-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
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