QuickView for Escitalopram (compound)

Summary
General Info

DrugBank

Identification

Name:	Escitalopram
Name (isomeric):	DB01175
Drug Type:	small molecule
Description:	S-enantiomer of citalopram.
Synonyms:	Escitalopram Oxalate
Brand:	Cipralex, Lexapro
Category:	Antidepressive Agents, Second-Generation, Serotonin Uptake Inhibitors
CAS number:	128196-01-0

Pharmacology

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.
Pharmacology:	Escitalopram is one of a class of antidepressants known as selective serotonin reuptake inhibitors (SSRIs). It is used to treat the depression associated with mood disorders. It is also used on occassion in the treatment of body dysmorphic disorder and anxiety. The antidepressant, antiobsessive-compulsive, and antibulimic actions of escitalopram ar... show more » Escitalopram is one of a class of antidepressants known as selective serotonin reuptake inhibitors (SSRIs). It is used to treat the depression associated with mood disorders. It is also used on occassion in the treatment of body dysmorphic disorder and anxiety. The antidepressant, antiobsessive-compulsive, and antibulimic actions of escitalopram are presumed to be linked to its inhibition of CNS neuronal uptake of serotonin. In vitro studies show that escitalopram is a potent and selective inhibitor of neuronal serotonin reuptake and has only very weak effects on norepinephrine and dopamine neuronal reuptake. Escitalopram has no significant affinity for adrenergic (alpha1, alpha2, beta), cholinergic, GABA, dopaminergic, histaminergic, serotonergic (5HT_1A, 5HT_1B, 5HT₂), or benzodiazepine receptors; antagonism of such receptors has been hypothesized to be associated with various anticholinergic, sedative, and cardiovascular effects for other psychotropic drugs. The chronic administration of escitalopram was found to downregulate brain norepinephrine receptors, as has been observed with other drugs effective in the treatment of major depressive disorder. Escitalopram does not inhibit monoamine oxidase. show less «
Mechanism of Action:	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 5HT_1A autoreceptors. SSRIs bind... show more » 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 5HT_1A autoreceptors. SSRIs bind with significantly less affinity to histamine, acetylcholine, and norepinephrine receptors than tricyclic antidepressant drugs. show less «
Absorption:	The absolute bioavailability of citalopram is about 80% relative to an intravenous dose.
Protein binding:	~56%
Biotransformation:	Mainly hepatic. Escitalopram undergoes N-demethylation to S-demethylcitalopram (S-DCT) and S-didemethylcitalopram (S-DDCT). CYP3A4 and CYP2C19 are the enzymes responsible for this N-demethylation reaction.
Route of elimination:	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).
Half Life:	27-32 hours
Clearance:	oral cl=600 mL/min [Following oral administrations]
Toxicity:	Signs of overdose include convulsions, coma, dizziness, hypotension, insomnia, nausea, vomiting, sinus tachycardia, somnolence, and ECG changes (including QT prolongation).
Affected organisms:	Humans and other mammals

Interactions

Food interaction:

Take without regard to meals.

Drug interaction:

Phenelzine	Possible severe adverse reaction with this combination
Almotriptan	Increased risk of CNS adverse effects
Triprolidine	The CNS depressants, Triprolidine and Escitalopram, may increase adverse/toxic effects due to additivity. Monitor for increased CNS depressant effects during concomitant therapy.
Selegiline	Possible severe adverse reaction with this combination
Treprostinil	The prostacyclin analogue, Treprostinil, increases the risk of bleeding when combined with the antiplatelet agent, Escitalopram. Monitor for increased bleeding during concomitant thearpy.

Phenelzine	Possible severe adverse reaction with this combination
Almotriptan	Increased risk of CNS adverse effects
Triprolidine	The CNS depressants, Triprolidine and Escitalopram, may increase adverse/toxic effects due to additivity. Monitor for increased CNS depressant effects during concomitant therapy.
Selegiline	Possible severe adverse reaction with this combination
Treprostinil	The prostacyclin analogue, Treprostinil, increases the risk of bleeding when combined with the antiplatelet agent, Escitalopram. Monitor for increased bleeding during concomitant thearpy.
Trimipramine	The SSRI, Escitalopram, may decrease the metabolism and clearance of Trimipramine. Increased risk of serotonin syndrome. Monitor for changes in Trimipramine efficacy and toxicity if Escitalopram is initiated, discontinued or dose changed.
Linezolid	Combination associated with possible serotoninergic syndrome
St. John's Wort	St. John's Wort increases the effect and toxicity of the SSRI, escitalopram.
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.
Pimozide	The SSRI, escitalopram, increases the effect and toxicity of pimozide.
Ticlopidine	Ticlopidine may decrease the metabolism and clearance of Escitalopram. Consider alternate therapy or monitor for adverse/toxic effects of Ambrisentan if Escitalopram is initiated, discontinued or dose changed.
Venlafaxine	Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Lumefantrine	Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
Isocarboxazid	Possible severe adverse reaction with this combination
Ziprasidone	Additive QTc-prolongation may occur increasing the risk of life-threatening ventricular arrhythmias and torsade de pointes. Concomitant therapy should be avoided.
Zuclopenthixol	Additive QTc prolongation may occur. Consider alternate therapy or use caution and monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
Tiaprofenic acid	Additive antiplatelet effects increase the risk of bleeding. Consider alternate therapy or monitor for increased bleeding.
Metoprolol	The SSRI, escitalopram, may increase the bradycardic effect of the beta-blocker, metoprolol.
Rasagiline	Possible severe adverse reaction with this combination
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.
Oxycodone	Increased risk of serotonin syndrome
Frovatriptan	Increased risk of CNS adverse effects
Telithromycin	Telithromycin may reduce clearance of Escitalopram. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Escitalopram if Telithromycin is initiated, discontinued or dose changed.
Carvedilol	The SSRI, escitalopram, may increase the bradycardic effect of the beta-blocker, carvedilol.
Sibutramine	Risk of serotoninergic syndrome
Artemether	Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
Eletriptan	Increased risk of CNS adverse effects
Sumatriptan	Increased risk of CNS adverse effects
Zolmitriptan	Use of two serotonin modulators, such as zolmitriptan and escitalopram, may increase the risk of serotonin syndrome. Consider alternate therapy or monitor for serotonin syndrome during concomitant therapy.
Tramadol	Tramadol may increase the risk of serotonin syndrome and seizures.
Ginkgo biloba	Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Rizatriptan	Increased risk of CNS adverse effects
Voriconazole	Voriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of escitalopram by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of escitalopram if voriconazole is initiated, discontinued or dose changed.
Propranolol	The SSRI, escitalopram, may increase the bradycardic effect of the beta-blocker, propranolol.
Ketoprofen	Concomitant therapy may result in additive antiplatelet effects and increase the risk of bleeding. Monitor for increased risk of bleeding during concomitant therapy.

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Targets

Sodium-dependent serotonin transporter

Sodium-dependent dopamine transporter

Sodium-dependent noradrenaline transporter

Alpha-1A adrenergic receptor

Muscarinic acetylcholine receptor M1

Histamine H1 receptor

Enzymes

Cytochrome P450 3A4

Cytochrome P450 2C19

Cytochrome P450 2D6