QuickView for Sertraline (compound)

Summary
General Info

PubChem

PubChem Compound 11722782

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

DrugBank

Identification

Name:	Sertraline
Name (isomeric):	DB01104
Drug Type:	small molecule
Description:	A selective serotonin uptake inhibitor that is used in the treatment of depression.
Synonyms:	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

Pharmacology

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.
Pharmacology:	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... show more » 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 clinically important anticholinergic, antihistamine, or adrenergic blocking activity. show less «
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... show more » 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. show less «
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

Interactions

Food interaction:

Avoid St.John's Wort.

Avoid alcohol.

Avoid taking with grapefruit juice.

Take with food.

Drug interaction:

Propranolol	The SSRI, sertraline, may increase the bradycardic effect of the beta-blocker, propranolol.
Zolmitriptan	Use 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.
Phenelzine	Possible severe adverse reaction with this combination
Almotriptan	Increased risk of CNS adverse effects
Tamoxifen	Sertraline may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Consider alternate therapy.

Propranolol	The SSRI, sertraline, may increase the bradycardic effect of the beta-blocker, propranolol.
Zolmitriptan	Use 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.
Phenelzine	Possible severe adverse reaction with this combination
Almotriptan	Increased risk of CNS adverse effects
Tamoxifen	Sertraline may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Consider alternate therapy.
Phenytoin	Sertraline increases the effect of hydantoin
Carbamazepine	Sertraline increases the effect of carbamazepine
Cilostazol	Sertraline increases the effect of cilostazol
Linezolid	Combination associated with possible serotoninergic syndrome
Tranylcypromine	Increased risk of serotonin syndrome. Concomitant therapy should be avoided. A significant washout period, dependent on the half-lives of the agents, should be employed between therapies.
Tramadol	Tramadol increases the risk of serotonin syndrome and seizures. Sertraline may increase Tramadol toxicity by decreasing Tramadol metabolism and clearance. Sertraline may decrease the effect of Tramadol by decreasing active metabolite production.
Venlafaxine	Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Isocarboxazid	Possible severe adverse reaction with this combination
Donepezil	Possible antagonism of action
Treprostinil	The prostacyclin analogue, Treprostinil, increases the risk of bleeding when combined with the antiplatelet agent, Sertraline. Monitor for increased bleeding during concomitant thearpy.
Fosphenytoin	Sertraline increases the effect of hydantoin
Tiaprofenic acid	Additive antiplatelet effects increase the risk of bleeding. Consider alternate therapy or monitor for increased bleeding.
Rasagiline	Possible severe adverse reaction with this combination
Pimozide	The SSRI, sertraline, increases the effect and toxicity of pimozide.
Tolmetin	Increased antiplatelet effects may enhance the risk of bleeding. Alternate therapy may be considered or monitor for inreased bleeding during concomitant therapy.
Trazodone	Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Naratriptan	Increased risk of CNS adverse effects
Desvenlafaxine	Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Tolterodine	Sertraline may decrease the metabolism and clearance of Tolterodine. Adjust Tolterodine dose and monitor for efficacy and toxicity.
Oxycodone	Increased risk of serotonin syndrome
Frovatriptan	Increased risk of CNS adverse effects
Erythromycin	Possible serotoninergic syndrome with this combination
Moclobemide	Possible severe adverse reaction with this combination
Tipranavir	Tipranavir increases the concentration of Sertraline. The Sertraline dose may require an adjustment.
Trimipramine	The SSRI, Sertraline, may decrease the metabolism and clearance of Trimipramine. Increased risk of serotonin syndrome. Monitor for changes in Trimipramine efficacy and toxicity if Sertraline is initiated, discontinued or dose changed.
Galantamine	Possible antagonism of action
Clarithromycin	Possible serotoninergic syndrome with this combination
Tamsulosin	Sertraline, a CYP3A4/2D6 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP3A4/2D6 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Sertraline is initiated, discontinued, or dose changed.
Eletriptan	Increased risk of CNS adverse effects
Metoprolol	The SSRI increases the effect of the beta-blocker
Ginkgo biloba	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Propafenone	Fluoxetine increases the effect and toxicity of propafenone
Ketoprofen	Concomitant therapy may result in additive antiplatelet effects and increase the risk of bleeding. Monitor for increased risk of bleeding during concomitant therapy.
Terbinafine	Terbinafine may reduce the metabolism and clearance of Sertraline. Consider alternate therapy or monitor for therapeutic/adverse effects of Sertraline if Terbinafine is initiated, discontinued or dose changed.
Clozapine	The antidepressant increases the effect of clozapine
Triprolidine	The CNS depressants, Triprolidine and Sertraline, may increase adverse/toxic effects due to additivity. Monitor for increased CNS depressant effects during concomitant therapy.
Carvedilol	The SSRI, sertraline, may increase the bradycardic effect of the beta-blocker, carvedilol.

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Targets

Sodium-dependent serotonin transporter

Sodium-dependent dopamine transporter

Enzymes

Amine oxidase [flavin-containing] B

Amine oxidase [flavin-containing] A

CYP2B protein

Transporters

Multidrug resistance protein 1