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QuickView for Sertraline (compound)

Name: Sertraline
PubChem Compound ID: 11722782
Description: A selective serotonin uptake inhibitor that is used in the treatment of depression.
Molecular formula: C17H17Cl2N
Molecular weight: 308.237 g/mol
Name: Sertraline
Name (isomeric): DB01104
Drug Type: small molecule
Description: A selective serotonin uptake inhibitor that is used in the treatment of depression.
Sertralina [Spanish]; Sertralinum [Latin]; Sertraline Hydrochloride
Brand: Zoloft, Apo-Sertraline, Lustral
Category: Antidepressants, Selective Serotonin Reuptake Inhibitors (SSRIs), Serotonin Uptake Inhibitors, Antidepressive Agents
CAS number: 79617-96-2
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.
Sertraline, an antidepressant drug similar to citalopram, fluoxetine, and paroxetine, is of the selective serotonin reuptake inhibitor (SSRI) type. Sertraline has one active metabolite and, like the other SSRIs, have less sedative, anticholinergic, and cardiovascular effects than the tricyclic antidepressant drugs because it does not have clinicall...
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Mechanism of Action:
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 suggest...
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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.
Protein binding: 98% bound to serum proteins, principally to albumin and α1-acid glycoprotein
Biotransformation: Extensively metabolized in the liver. Sertraline metabolism involves N-demethylation, N-hydroxylation, oxidative deamination, and glucuronidation of sertraline carbamic acid. Sertraline undergoes N-demethylation primarily catalyzed by cytochrome P450 (CYP) 2B6, with CYP2C19, CYP3A4 and CYP2D6 contributing to a lesser extent. Deamination occurs via CYP3A4 and CYP2C19. In vitro studies have shown that monoamine oxidase A and B may also catalyze sertraline deamination. Sertraline N-carbamoyl glucuronidation has also been observed in human liver microsomes.
Route of elimination: Sertraline is extensively metabolized and excretion of unchanged drug in urine is a minor route of elimination.
Half Life: The elimination half-life of sertraline is approximately 25-26 hours. The elimination half-life of desmethylsertraline is approximately 62-104 hours.
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.
Affected organisms: Humans and other mammals
Food interaction:
Avoid St.John's Wort.
Avoid alcohol.
Avoid taking with grapefruit juice.
Take with food.
Drug interaction:
PropranololThe SSRI, sertraline, may increase the bradycardic effect of the beta-blocker, propranolol.
ZolmitriptanUse of two serotonin modulators, such as zolmitriptan and sertraline, increases the risk of serotonin syndrome. Consider alternate therapy or monitor for serotonin syndrome during concomitant therapy.
PhenelzinePossible severe adverse reaction with this combination
AlmotriptanIncreased risk of CNS adverse effects
TamoxifenSertraline may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Consider alternate therapy.
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