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Details

Stereochemistry ACHIRAL
Molecular Formula C21H25N3O2S
Molecular Weight 383.507
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of QUETIAPINE

SMILES

OCCOCCN1CCN(CC1)C2=NC3=CC=CC=C3SC4=CC=CC=C24

InChI

InChIKey=URKOMYMAXPYINW-UHFFFAOYSA-N
InChI=1S/C21H25N3O2S/c25-14-16-26-15-13-23-9-11-24(12-10-23)21-17-5-1-3-7-19(17)27-20-8-4-2-6-18(20)22-21/h1-8,25H,9-16H2

HIDE SMILES / InChI

Molecular Formula C21H25N3O2S
Molecular Weight 383.507
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/12973385 | https://www.ncbi.nlm.nih.gov/pubmed/10839333

Quetiapine, marketed as SEROQUEL XR, is an atypical antipsychotic approved for the treatment of schizophrenia, bipolar disorder, and along with an antidepressant to treat major depressive disorder. The mechanism of action of SEROQUEL XR in the treatment of schizophrenia, bipolar disorder and major depressive disorder (MDD), is unknown. However, its efficacy in schizophrenia could be mediated through a combination of dopamine type 2 (D2) and serotonin type 2A (5HT2A) antagonism. The active metabolite, N-desalkyl quetiapine (norquetiapine), has similar activity at D2, but greater activity at 5HT2A receptors, than the parent drug (quetiapine). Quetiapine’s efficacy in bipolar depression and MDD may partly be explained by the high affinity and potent inhibitory effects that norquetiapine exhibits for the norepinephrine transporter. Antagonism at receptors other than dopamine and serotonin with similar or greater affinities may explain some of the other effects of quetiapine and norquetiapine: antagonism at histamine H1 receptors may explain the somnolence, antagonism at adrenergic α1b receptors may explain the orthostatic hypotension, and antagonism at muscarinic M1 receptors may explain the anticholinergic effects. Quetiapine and norquetiapine have affinity for multiple neurotransmitter receptors including dopamine D1 and D2, serotonin 5HT1A and 5HT2A, histamine H1, muscarinic M1, and adrenergic α1b and α2 receptors. Quetiapine differs from norquetiapine in having no appreciable affinity for muscarinic M1 receptors whereas norquetiapine has high affinity. Quetiapine and norquetiapine lack appreciable affinity for benzodiazepine receptors.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
SEROQUEL XR

Approved Use

1.1 Schizophrenia. SEROQUEL XR is indicated for the treatment of schizophrenia. The efficacy of SEROQUEL XR in schizophrenia was established in one 6-week and one maintenance trial in adults with schizophrenia. Efficacy was supported by three 6 week trials in adults with schizophrenia and one 6-week trial in adolescents with schizophrenia (13-17 years) treated with SEROQUEL. 1.2 Bipolar Disorder SEROQUEL XR is indicated for the acute treatment of manic or mixed episodes associated with bipolar I disorder, both as monotherapy and as an adjunct to lithium or divalproex. The efficacy of SEROQUEL XR in manic or mixed episodes of bipolar I disorder was established in one 3-week trial in adults with manic or mixed episodes associated with bipolar I disorder. Efficacy was supported by two 12-week monotherapy trials and one 3-week adjunctive trial in adults with manic episodes associated with bipolar I disorder as well as one 3-week monotherapy trial in children and adolescents (10– 17 years) with manic episodes associated with bipolar I disorder treated with SEROQUEL. 1.3 Adjunctive Treatment of Major Depressive Disorder (MDD) ROQUEL XR is indicated for use as adjunctive therapy to antidepressants for the treatment of MDD. The efficacy of SEROQUEL XR as adjunctive therapy to antidepressants in MDD was established in two 6-week trials in adults with MDD who had an inadequate response to antidepressant treatment.

Launch Date

2007
Primary
SEROQUEL XR

Approved Use

1.1 Schizophrenia. SEROQUEL XR is indicated for the treatment of schizophrenia. The efficacy of SEROQUEL XR in schizophrenia was established in one 6-week and one maintenance trial in adults with schizophrenia. Efficacy was supported by three 6 week trials in adults with schizophrenia and one 6-week trial in adolescents with schizophrenia (13-17 years) treated with SEROQUEL. 1.2 Bipolar Disorder SEROQUEL XR is indicated for the acute treatment of manic or mixed episodes associated with bipolar I disorder, both as monotherapy and as an adjunct to lithium or divalproex. The efficacy of SEROQUEL XR in manic or mixed episodes of bipolar I disorder was established in one 3-week trial in adults with manic or mixed episodes associated with bipolar I disorder. Efficacy was supported by two 12-week monotherapy trials and one 3-week adjunctive trial in adults with manic episodes associated with bipolar I disorder as well as one 3-week monotherapy trial in children and adolescents (10– 17 years) with manic episodes associated with bipolar I disorder treated with SEROQUEL. 1.3 Adjunctive Treatment of Major Depressive Disorder (MDD) ROQUEL XR is indicated for use as adjunctive therapy to antidepressants for the treatment of MDD. The efficacy of SEROQUEL XR as adjunctive therapy to antidepressants in MDD was established in two 6-week trials in adults with MDD who had an inadequate response to antidepressant treatment.

Launch Date

2007
Palliative
SEROQUEL XR

Approved Use

1.1 Schizophrenia. SEROQUEL XR is indicated for the treatment of schizophrenia. The efficacy of SEROQUEL XR in schizophrenia was established in one 6-week and one maintenance trial in adults with schizophrenia. Efficacy was supported by three 6 week trials in adults with schizophrenia and one 6-week trial in adolescents with schizophrenia (13-17 years) treated with SEROQUEL. 1.2 Bipolar Disorder SEROQUEL XR is indicated for the acute treatment of manic or mixed episodes associated with bipolar I disorder, both as monotherapy and as an adjunct to lithium or divalproex. The efficacy of SEROQUEL XR in manic or mixed episodes of bipolar I disorder was established in one 3-week trial in adults with manic or mixed episodes associated with bipolar I disorder. Efficacy was supported by two 12-week monotherapy trials and one 3-week adjunctive trial in adults with manic episodes associated with bipolar I disorder as well as one 3-week monotherapy trial in children and adolescents (10– 17 years) with manic episodes associated with bipolar I disorder treated with SEROQUEL. 1.3 Adjunctive Treatment of Major Depressive Disorder (MDD) ROQUEL XR is indicated for use as adjunctive therapy to antidepressants for the treatment of MDD. The efficacy of SEROQUEL XR as adjunctive therapy to antidepressants in MDD was established in two 6-week trials in adults with MDD who had an inadequate response to antidepressant treatment.

Launch Date

2007
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
58.23 ng/mL
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
QUETIAPINE FUMARATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
58.42 ng/mL
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
QUETIAPINE FUMARATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
60.11 ng/mL
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
QUETIAPINE FUMARATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
187.44 ng × h/mL
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
QUETIAPINE FUMARATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
197.55 ng × h/mL
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
QUETIAPINE FUMARATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
190.39 ng × h/mL
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
QUETIAPINE FUMARATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3.86 h
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
QUETIAPINE FUMARATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
3.85 h
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
QUETIAPINE FUMARATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
3.98 h
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
QUETIAPINE FUMARATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
17%
unknown, unknown
QUETIAPINE FUMARATE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes [Km 12.3 uM]
yes
yes
yes (co-administration study)
Comment: all metabolites (5) formed from CYP3A4 metabolism; ketoconazole reduces clearance by 84%, increasing maximum plasma concentration by 335%; phenytoin increases clearance by 5-fold
Page: 4.0
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Review of atypical antipsychotics and weight gain.
2001
New antidepressive and antipsychotic drugs in juvenile neuronal ceroid lipofuscinoses--a pilot study.
2001
Clinical pharmacokinetics of quetiapine: an atypical antipsychotic.
2001
Hypothesis and hypothesis testing in the clinical trial.
2001
Asymptomatic QTc prolongation associated with quetiapine fumarate overdose in a patient being treated with risperidone.
2001 Apr
Antipsychotic metabolic effects: weight gain, diabetes mellitus, and lipid abnormalities.
2001 Apr
Quetiapine for Tourette's syndrome.
2001 Apr
D(2) and 5HT(2A) receptor occupancy of different doses of quetiapine in schizophrenia: a PET study.
2001 Apr
The health economic implications of treatment with quetiapine: an audit of long-term treatment for patients with chronic schizophrenia.
2001 Aug
In vivo 5-HT2A receptor blockade by quetiapine: an R91150 single photon emission tomography study.
2001 Aug
Novel antipsychotics and severe hyperlipidemia.
2001 Aug
Management of psychosis in Parkinson's disease.
2001 Aug
Ziprasidone: a novel antipsychotic agent with a unique human receptor binding profile.
2001 Aug 17
Broad therapeutic uses of atypical antipsychotic medications.
2001 Dec 1
Long-term remission of schizophrenia in an adolescent treated with quetiapine.
2001 Fall
New onset diabetes and atypical antipsychotics.
2001 Feb
The effects of concomitant phenytoin administration on the steady-state pharmacokinetics of quetiapine.
2001 Feb
Behavioral approach to nondyskinetic dopamine antagonists: identification of seroquel.
2001 Feb 1
Cost effectiveness of the newer atypical antipsychotics: a review of the pharmacoeconomic research evidence.
2001 Jan
Quetiapine and obsessive-compulsive symptoms (OCS): case report and review of atypical antipsychotic-induced OCS.
2001 Jan
New Rx for psychoses in Alzheimer's, Parkinson's.
2001 Jan
Consistency of atypical antipsychotic superiority to placebo in recent clinical trials.
2001 Jan 1
Use of atypical antipsychotics in mood disorders.
2001 Jul
Acute neutropenia in a patient treated with quetiapine.
2001 Jul-Aug
Diabetes mellitus associated with atypical antipsychotic medications: new case report and review of the literature.
2001 Jul-Aug
Ziprasidone: a new atypical antipsychotic.
2001 Jun
Neuropsychological change in patients with schizophrenia after treatment with quetiapine or haloperidol.
2001 Mar
Quetiapine-associated hypomania in a woman with schizoaffective disorder.
2001 Mar
Differing tolerability profiles among atypical antipsychotics.
2001 Mar
Reduction of tardive dyskinesia with quetiapine.
2001 Mar 1
Pharmacotherapy of target symptoms in autistic spectrum disorders.
2001 May
Long-term effects of olanzapine, risperidone, and quetiapine on dopamine receptor types in regions of rat brain: implications for antipsychotic drug treatment.
2001 May
Successful outcome using quetiapine in a case of treatment-resistant schizophrenia with assaultive behavior.
2001 May 30
A comparison of the relative safety, efficacy, and tolerability of quetiapine and risperidone in outpatients with schizophrenia and other psychotic disorders: the quetiapine experience with safety and tolerability (QUEST) study.
2001 Nov
Antipsychotic drugs: prolonged QTc interval, torsade de pointes, and sudden death.
2001 Nov
[Quetiapine poisoning].
2001 Nov 17
Ziprasidone: profile on safety.
2001 Oct
Agranulocytosis and granulocytopenia associated with quetiapine.
2001 Oct
Quetiapine: efficacy and tolerability in schizophrenia.
2001 Oct
Quetiapine-related tardive dyskinesia.
2001 Oct
Inverse agonist actions of typical and atypical antipsychotic drugs at the human 5-hydroxytryptamine(2C) receptor.
2001 Oct
Efficacy of antipsychotic agents at human 5-HT(1A) receptors determined by [3H]WAY100,635 binding affinity ratios: relationship to efficacy for G-protein activation.
2001 Oct 5
A case of depersonalization-derealization syndrome during treatment with quetiapine.
2001 Sep
Priapism from quetiapine overdose: first report and proposal of mechanism.
2001 Sep
Symptom reduction and suicide risk among patients treated with placebo in antipsychotic clinical trials: an analysis of the food and drug administration database.
2001 Sep
Quetiapine treatment of children with Tourette's syndrome: report of two cases.
2001 Summer
Ziprasidone: an atypical antipsychotic drug for the treatment of schizophrenia.
2002 Jan
Quetiapine augmentation of serotonin reuptake inhibitors in obsessive-compulsive disorder.
2002 Jan
EEG abnormalities during treatment with typical and atypical antipsychotics.
2002 Jan
[Drug-induced akathisia].
2002 Jan 19
Patents

Sample Use Guides

Schizophrenia- Adults: Day 1: 300 mg/day Dose increases can be made at intervals as short as 1 day and in increments of up to 300 mg/day Schizophrenia-Adolescents: (13 to 17 years): Day 1: 50 mg/day; Day 2: 100 mg/day; Day 3: 200 mg/day; Day 4: 300 mg/day; Day 5: 400 mg/day; Bipolar I Disorder manic or mixed-Acute monotherapy or adjunct to lithium or divalproex-Adults: Day 1: 300 mg/day; Day 2: 600 mg/day; Day 3: between 400 and 800 mg/day. Major Depressive Disorder Adjunctive Therapy with Antidepressants: Adults: Day 1: 50 mg/day; Day 2: 50 mg/day; Day 3: 150 mg/day Bipolar I Disorder, manic ­Acute monotherapy: Children and Adolescents (10 to 17 years) : Day 1: 50 mg/day; Day 2: 100 mg/day; Day 3: 200 mg/day; Day 4: 300 mg/day; Day 5: 400 mg/day.
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment: The antidepressant activity of quetiapine is considered to be mediated by the active metabolite N-desalkylquetiapine, which is mainly formed by CYP3A4. N-desalkylquetiapine is metabolized by both CYP2D6 and CYP3A4 in vitro with preference for the former enzyme. The pharmacologically active metabolite, 7-hydroxy-N-desalkylquetiapine, was exclusively formed by CYP2D6, whereas the two other metabolites were mainly formed by CYP3A4.
Unknown
Substance Class Chemical
Created
by admin
on Wed Apr 02 09:03:14 GMT 2025
Edited
by admin
on Wed Apr 02 09:03:14 GMT 2025
Record UNII
BGL0JSY5SI
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
QUETIAPINE
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
NORSIC
Preferred Name English
QUETIAPINE [MI]
Common Name English
quetiapine [INN]
Common Name English
QUETIAPINE EXTENDED RELEASE
Common Name English
Quetiapine [WHO-DD]
Common Name English
QUETIAPINE [VANDF]
Common Name English
ETHANOL, 2-(2-(4-DIBENZO(B,F)(1,4)THIAZEPIN-11-YL-1-PIPERAZINYL)ETHOXY)-
Systematic Name English
QUETIAPINE [HSDB]
Common Name English
NSC-758918
Code English
2-(2-(4-DIBENZO(B,F)(1,4)THIAZEPIN-11-YLPIPERAZIN-1-YL)ETHOXY)ETHANOL
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C66885
Created by admin on Wed Apr 02 09:03:14 GMT 2025 , Edited by admin on Wed Apr 02 09:03:14 GMT 2025
WHO-ATC N05AH04
Created by admin on Wed Apr 02 09:03:14 GMT 2025 , Edited by admin on Wed Apr 02 09:03:14 GMT 2025
WHO-VATC QN05AH04
Created by admin on Wed Apr 02 09:03:14 GMT 2025 , Edited by admin on Wed Apr 02 09:03:14 GMT 2025
LIVERTOX NBK548616
Created by admin on Wed Apr 02 09:03:14 GMT 2025 , Edited by admin on Wed Apr 02 09:03:14 GMT 2025
NDF-RT N0000175430
Created by admin on Wed Apr 02 09:03:14 GMT 2025 , Edited by admin on Wed Apr 02 09:03:14 GMT 2025
NCI_THESAURUS C29710
Created by admin on Wed Apr 02 09:03:14 GMT 2025 , Edited by admin on Wed Apr 02 09:03:14 GMT 2025
Code System Code Type Description
LACTMED
Quetiapine
Created by admin on Wed Apr 02 09:03:14 GMT 2025 , Edited by admin on Wed Apr 02 09:03:14 GMT 2025
PRIMARY
ChEMBL
CHEMBL716
Created by admin on Wed Apr 02 09:03:14 GMT 2025 , Edited by admin on Wed Apr 02 09:03:14 GMT 2025
PRIMARY
SMS_ID
100000081102
Created by admin on Wed Apr 02 09:03:14 GMT 2025 , Edited by admin on Wed Apr 02 09:03:14 GMT 2025
PRIMARY
MERCK INDEX
m9425
Created by admin on Wed Apr 02 09:03:14 GMT 2025 , Edited by admin on Wed Apr 02 09:03:14 GMT 2025
PRIMARY Merck Index
DRUG BANK
DB01224
Created by admin on Wed Apr 02 09:03:14 GMT 2025 , Edited by admin on Wed Apr 02 09:03:14 GMT 2025
PRIMARY
EPA CompTox
DTXSID9023546
Created by admin on Wed Apr 02 09:03:14 GMT 2025 , Edited by admin on Wed Apr 02 09:03:14 GMT 2025
PRIMARY
RXCUI
51272
Created by admin on Wed Apr 02 09:03:14 GMT 2025 , Edited by admin on Wed Apr 02 09:03:14 GMT 2025
PRIMARY RxNorm
DAILYMED
BGL0JSY5SI
Created by admin on Wed Apr 02 09:03:14 GMT 2025 , Edited by admin on Wed Apr 02 09:03:14 GMT 2025
PRIMARY
EVMPD
SUB10192MIG
Created by admin on Wed Apr 02 09:03:14 GMT 2025 , Edited by admin on Wed Apr 02 09:03:14 GMT 2025
PRIMARY
HSDB
7557
Created by admin on Wed Apr 02 09:03:14 GMT 2025 , Edited by admin on Wed Apr 02 09:03:14 GMT 2025
PRIMARY
NCI_THESAURUS
C61917
Created by admin on Wed Apr 02 09:03:14 GMT 2025 , Edited by admin on Wed Apr 02 09:03:14 GMT 2025
PRIMARY
INN
7467
Created by admin on Wed Apr 02 09:03:14 GMT 2025 , Edited by admin on Wed Apr 02 09:03:14 GMT 2025
PRIMARY
DRUG CENTRAL
2337
Created by admin on Wed Apr 02 09:03:14 GMT 2025 , Edited by admin on Wed Apr 02 09:03:14 GMT 2025
PRIMARY
IUPHAR
50
Created by admin on Wed Apr 02 09:03:14 GMT 2025 , Edited by admin on Wed Apr 02 09:03:14 GMT 2025
PRIMARY
CHEBI
8707
Created by admin on Wed Apr 02 09:03:14 GMT 2025 , Edited by admin on Wed Apr 02 09:03:14 GMT 2025
PRIMARY
MESH
C069541
Created by admin on Wed Apr 02 09:03:14 GMT 2025 , Edited by admin on Wed Apr 02 09:03:14 GMT 2025
PRIMARY
CAS
111974-69-7
Created by admin on Wed Apr 02 09:03:14 GMT 2025 , Edited by admin on Wed Apr 02 09:03:14 GMT 2025
PRIMARY
FDA UNII
BGL0JSY5SI
Created by admin on Wed Apr 02 09:03:14 GMT 2025 , Edited by admin on Wed Apr 02 09:03:14 GMT 2025
PRIMARY
PUBCHEM
5002
Created by admin on Wed Apr 02 09:03:14 GMT 2025 , Edited by admin on Wed Apr 02 09:03:14 GMT 2025
PRIMARY
NSC
758918
Created by admin on Wed Apr 02 09:03:14 GMT 2025 , Edited by admin on Wed Apr 02 09:03:14 GMT 2025
PRIMARY
WIKIPEDIA
QUETIAPINE
Created by admin on Wed Apr 02 09:03:14 GMT 2025 , Edited by admin on Wed Apr 02 09:03:14 GMT 2025
PRIMARY
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