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Quetiapine

Catalog No. DB01224 Name DrugBank
CAS Number 111974-69-7 Website http://www.ualberta.ca/
M. F. C21H25N3O2S Telephone (780) 492-3111
M. W. 383.5071 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 1094

SYNONYMS

IUPAC name
2-[2-(4-{2-thia-9-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-10-yl}piperazin-1-yl)ethoxy]ethan-1-ol
IUPAC Traditional name
quetiapine
Brand Name
Seroquel XR
Seroquel
Synonyms
Quetiapine hemifumarate
Quetiapine fumarate

DATABASE IDS

CAS Number 111974-69-7
PubChem SID 46504800
PubChem CID 5002

PROPERTIES

Hydrophobicity(logP) 2.8
Solubility Moderate

DETAILS

Description (English)
Item Information
Drug Groups approved
Description Quetiapine is indicated for the treatment of schizophrenia as well as for the treatment of acute manic episodes associated with bipolar I disorder. The antipsychotic effect of quetiapine is thought by some to be mediated through antagonist activity at dopamine and serotonin receptors. Specifically the D1 and D2 dopamine, the alpha 1 adrenoreceptor and alpha 2 adrenoreceptor, and 5-HT1A and 5-HT2 serotonin receptor subtypes are antagonized. Quetiapine also has an antagonistic effect on the histamine H1 receptor.
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-HT1A 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.
Toxicity Symptoms of overdose include drowsiness and sedation, tachycardia, and hypotension.
Affected Organisms
Humans and other mammals
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.
Absorption Rapidly and well absorbed.
Half Life 6 hours
Protein Binding 83%
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.
Distribution * 10±4 L/kg
References
Dev V, Raniwalla J: Quetiapine: a review of its safety in the management of schizophrenia. Drug Saf. 2000 Oct;23(4):295-307. [Pubmed]
Mukaddes NM, Abali O: Quetiapine treatment of children and adolescents with Tourette's disorder. J Child Adolesc Psychopharmacol. 2003 Fall;13(3):295-9. [Pubmed]
Tallerico T, Novak G, Liu IS, Ulpian C, Seeman P: Schizophrenia: elevated mRNA for dopamine D2(Longer) receptors in frontal cortex. Brain Res Mol Brain Res. 2001 Mar 5;87(2):160-5. [Pubmed]
Urichuk L, Prior TI, Dursun S, Baker G: Metabolism of atypical antipsychotics: involvement of cytochrome p450 enzymes and relevance for drug-drug interactions. Curr Drug Metab. 2008 Jun;9(5):410-8. [Pubmed]
External Links
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REFERENCES

  • Dev V, Raniwalla J: Quetiapine: a review of its safety in the management of schizophrenia. Drug Saf. 2000 Oct;23(4):295-307. Pubmed
  • Mukaddes NM, Abali O: Quetiapine treatment of children and adolescents with Tourette's disorder. J Child Adolesc Psychopharmacol. 2003 Fall;13(3):295-9. Pubmed
  • Tallerico T, Novak G, Liu IS, Ulpian C, Seeman P: Schizophrenia: elevated mRNA for dopamine D2(Longer) receptors in frontal cortex. Brain Res Mol Brain Res. 2001 Mar 5;87(2):160-5. Pubmed
  • Urichuk L, Prior TI, Dursun S, Baker G: Metabolism of atypical antipsychotics: involvement of cytochrome p450 enzymes and relevance for drug-drug interactions. Curr Drug Metab. 2008 Jun;9(5):410-8. Pubmed