QuickView for Quetiapine (compound)

Summary
General Info

PubChem

PubChem Compound 5002

Name:	quetiapine
PubChem Compound ID:	5002
Molecular formula:	C₂₁H₂₅N₃O₂S
Molecular weight:	383.508 g/mol
Synonyms:	111974-69-7; Ethanol, 2-(2-(4-dibenzo(b,f)(1,4)thiazepin-11-yl-1-piperazinyl)ethoxy)-; AIDS-085406; 2-[2-(4-Dibenzo[b,f][1,4]thiazepin-11-yl-1-piperazinyl)ethoxy]ethanol; ZM 204,636; Seroquel; ZD5077; AIDS085406; Ethanol, 2-[2-(4-dibenzo[b,f][1,4]thiazepin-11-yl-1-piperazinyl)ethoxy]-; 2-(2-(4-DIBENZO(B,F)(1,4)THIAZEPIN-11-YL-1-PIPERAZINYL)ETHOXY)ETHANOL FUMARATE (. show more » 111974-69-7; Ethanol, 2-(2-(4-dibenzo(b,f)(1,4)thiazepin-11-yl-1-piperazinyl)ethoxy)-; AIDS-085406; 2-[2-(4-Dibenzo[b,f][1,4]thiazepin-11-yl-1-piperazinyl)ethoxy]ethanol; ZM 204,636; Seroquel; ZD5077; AIDS085406; Ethanol, 2-[2-(4-dibenzo[b,f][1,4]thiazepin-11-yl-1-piperazinyl)ethoxy]-; 2-(2-(4-DIBENZO(B,F)(1,4)THIAZEPIN-11-YL-1-PIPERAZINYL)ETHOXY)ETHANOL FUMARATE (; C07397; ICI 204,636; 2-(2-(4-Dibenzo(b,f)(1,4)thiazepin-11-yl-1-piperazinyl)ethoxy)ethanol; Quetiapine; 111974-72-2; Seroquel (Fumarate) show less «

DrugBank

Identification

Name:	quetiapine
Name (isomeric):	DB01224
Drug Type:	small molecule
Synonyms:	Quetiapine fumarate; Quetiapine hemifumarate
Brand:	Seroquel XR, Seroquel
Category:	Antipsychotic Agents, Antipsychotics
CAS number:	111974-69-7

Pharmacology

Indication:	For the treatment of schizophrenia and related psychotic disorders.
Pharmacology:	Quetiapine is a psychotropic agent belonging to the chemical class of benzisoxazole derivatives and is indicated for the treatment of schizophrenia. Quetiapine is a selective monoaminergic antagonist with high affinity for the serotonin Type 2 (5HT₂), and dopamine type 2 (D2) receptors. Quetiapine is an antagonist at serotonin 5-HT_{1... show more »} Quetiapine is a psychotropic agent belonging to the chemical class of benzisoxazole derivatives and is indicated for the treatment of schizophrenia. Quetiapine is a selective monoaminergic antagonist with high affinity for the serotonin Type 2 (5HT₂), and dopamine type 2 (D2) receptors. Quetiapine is an antagonist at serotonin 5-HT_1A and 5HT₂, dopamine D1 and D2, histamine H1, and adrenergic alpha 1 and alpha 2 receptors. Quetiapine has no significant affinity for cholinergic muscarinic or benzodiazepine receptors. Drowsiness and orthostatic hypotension associated with use of quetiapine may be explained by its antagonism of histamine H1 and adrenergic alpha 1 receptors, respectively. Quetiapine's antagonism of adrenergic a1 receptors may explain the orthostatic hypotension observed with this drug. show less «
Mechanism of Action:	Quetiapine's antipsychotic activity is likely due to a combination of antagonism at D2 receptors in the mesolimbic pathway and 5HT2A receptors in the frontal cortex. Antagonism at D2 receptors relieves positive symptoms while antagonism at 5HT2A receptors relieves negative symptoms of schizophrenia.
Absorption:	Rapidly and well absorbed.
Protein binding:	83%
Biotransformation:	Hepatic. The major metabolic pathways are sulfoxidation, mediated by cytochrome P450 3A4 (CYP3A4), and oxidation of the terminal alcohol to a carboxylic acid. The major sulfoxide metabolite of quetiapine is inactive. Quetiapine also undergoes hydroxylation of the dibenzothiazepine ring, O-deakylation, N-dealkylation, and phase II conjugation. The 7-hydroxy and 7-hydroxy- N-delakylated metabolites appear to be active, but are present in very low concentrations.
Route of elimination:	Elimination of quetiapine is mainly via hepatic metabolism. Following a single oral dose of 14C-quetiapine, less than 1% of the administered dose was excreted as unchanged drug, indicating that quetiapine is highly metabolized. Approximately 73% and 20% of the dose was recovered in the urine and feces, respectively.
Half Life:	6 hours
Toxicity:	Symptoms of overdose include drowsiness and sedation, tachycardia, and hypotension.
Affected organisms:	Humans and other mammals

Interactions

Food interaction:

Avoid alcohol.

Take without regard to meals.

Drug interaction:

Mephenytoin	Phenytoin decreases the effect of quetiapine
Triprolidine	Triprolidine and Quetiapine, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Additive CNS depressant effects may also occur. Monitor for enhanced anticholinergic and CNS depressant effects.
Tetrabenazine	May cause dopamine deficiency. Monitor for Tetrabenazine adverse effects.
Erythromycin	The macrolide, erythromycin, may increase the effect and toxicity of quetiapine.
Phenytoin	Phenytoin decreases the effect of quetiapine

Mephenytoin	Phenytoin decreases the effect of quetiapine
Triprolidine	Triprolidine and Quetiapine, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Additive CNS depressant effects may also occur. Monitor for enhanced anticholinergic and CNS depressant effects.
Tetrabenazine	May cause dopamine deficiency. Monitor for Tetrabenazine adverse effects.
Erythromycin	The macrolide, erythromycin, may increase the effect and toxicity of quetiapine.
Phenytoin	Phenytoin decreases the effect of quetiapine
Lumefantrine	Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
Donepezil	Possible antagonism of action
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).
Fosphenytoin	Phenytoin decreases the effect of quetiapine
Ethotoin	Phenytoin decreases the effect of quetiapine
Tacrine	The therapeutic effects of the central acetylcholinesterase inhibitor (AChEI), Tacrine, and/or the anticholinergic/antipsychotic, Quetiapine, may be reduced due to antagonism. This interaction may be beneficial when the anticholinergic action is a side effect. AChEIs may also augment the central neurotoxic effect of antipsychotics. Monitor for extrapyramidal symptoms and decreased efficacy of both agents.
Thiothixene	May cause additive QTc-prolonging effects. Increased risk of ventricular arrhythmias. Consider alternate therapy. Thorough risk:benefit assessment is required prior to co-administration.
Vorinostat	Additive QTc prolongation may occur. Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
Clarithromycin	The macrolide, clarithromycin, may increase the effect and toxicity of quetiapine.
Trimethobenzamide	Trimethobenzamide and Quetiapine, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Galantamine	Possible antagonism of action
Ziprasidone	Additive QTc-prolonging effects may increase the risk of severe arrhythmias. Concomitant therapy is contraindicated.
Quinupristin	This combination presents an increased risk of toxicity
Artemether	Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
Tacrolimus	Additive QTc-prolongation may occur increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution.
Toremifene	Additive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Consider alternate therapy. A thorough risk:benefit assessment is required prior to co-administration.
Trospium	Trospium and Quetiapine, two anticholinergics, may cause additive anticholinergic effects and enhanced adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Trimipramine	Additive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution.
Voriconazole	Voriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of quetiapine by decreasing its metabolism. Additive QTc prolongation may also occur. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of quetiapine if voriconazole is initiated, discontinued or dose changed.
Ketoconazole	Ketoconazole may increase the therapeutic and adverse effects of quetiapine.
Rivastigmine	Possible antagonism of action
Telithromycin	Telithromycin may reduce clearance of Quetiapine. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Quetiapine if Telithromycin is initiated, discontinued or dose changed.