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Details

Stereochemistry ACHIRAL
Molecular Formula 2C21H25N3O2S.C4H4O4
Molecular Weight 883.086
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of QUETIAPINE FUMARATE

SMILES

OC(=O)\C=C\C(O)=O.OCCOCCN1CCN(CC1)C2=NC3=C(SC4=C2C=CC=C4)C=CC=C3.OCCOCCN5CCN(CC5)C6=NC7=C(SC8=C6C=CC=C8)C=CC=C7

InChI

InChIKey=ZTHJULTYCAQOIJ-WXXKFALUSA-N
InChI=1S/2C21H25N3O2S.C4H4O4/c2*25-14-16-26-15-13-23-9-11-24(12-10-23)21-17-5-1-3-7-19(17)27-20-8-4-2-6-18(20)22-21;5-3(6)1-2-4(7)8/h2*1-8,25H,9-16H2;1-2H,(H,5,6)(H,7,8)/b;;2-1+

HIDE SMILES / InChI

Molecular Formula C21H25N3O2S
Molecular Weight 383.507
Charge 0
Count
MOL RATIO 2 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

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.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
SEROQUEL XR
Primary
SEROQUEL XR
Palliative
SEROQUEL XR

Cmax

ValueDoseCo-administeredAnalytePopulation
58.23 ng/mL
25 mg single, oral
QUETIAPINE FUMARATE plasma
Homo sapiens
60.11 ng/mL
25 mg single, oral
QUETIAPINE FUMARATE plasma
Homo sapiens
58.42 ng/mL
25 mg single, oral
QUETIAPINE FUMARATE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
187.44 ng × h/mL
25 mg single, oral
QUETIAPINE FUMARATE plasma
Homo sapiens
190.39 ng × h/mL
25 mg single, oral
QUETIAPINE FUMARATE plasma
Homo sapiens
197.55 ng × h/mL
25 mg single, oral
QUETIAPINE FUMARATE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
3.86 h
25 mg single, oral
QUETIAPINE FUMARATE plasma
Homo sapiens
3.98 h
25 mg single, oral
QUETIAPINE FUMARATE plasma
Homo sapiens
3.85 h
25 mg single, oral
QUETIAPINE FUMARATE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
17%
unknown, unknown
QUETIAPINE FUMARATE plasma
Homo sapiens

Doses

AEs

OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
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
Unknown
Substance Class Chemical
Record UNII
2S3PL1B6UJ
Record Status Validated (UNII)
Record Version