Quetiapine (CHEM002082)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (30)XML
Record Information
Version1.0
Creation Date2009-07-05 02:44:12 UTC
Update Date2026-05-14 16:58:52 UTC
Accession NumberCHEM002082
Identification
Common NameQuetiapine
ClassSmall Molecule
DescriptionThe most common side effect is sedation, and is prescribed specifically for this effect in patients with sleep disorders. Seroquel will put the patient into a drowsy state, and will help the patient fall asleep. It is one of the most sedating of all anti psychotic drugs, rivaling even the most sedating older antipsychotics. Many prescriptions call for the entire dose to be taken before bedtime because of its sedative effects. Although quetiapine is approved by the FDA for the treatment of schizophrenia and bipolar disorder, it is frequently prescribed for off-label purposes including insomnia or the treatment of anxiety disorders. Due to its sedative side effects, reports of quetiapine abuse (sometimes by insufflating crushed tablets) have emerged in medical literature; Quetiapine belongs to a series of neuroleptics known as atypical antipsychotics, which have become increasingly popular alternatives to typical antipsychotics such as haloperidol. Quetiapine HAS approvals for the treatment of schizophrenia and acute mania in bipolar disorder. It is also used off-label to treat other disorders, such as post-traumatic stress disorder, alcoholism, obsessive compulsive disorder, anxiety disorders, hallucinations in Parkinson's disease patients using ropinirole, and as a sedative for those with sleep disorders. The most common side effect is sedation, and is prescribed specifically for this effect in patients with sleep disorders. Seroquel will put the patient into a drowsy state, and will help the patient fall asleep. It is one of the most sedating of all anti psychotic drugs, rivaling even the most sedating older antipsychotics. Many prescriptions call for the entire dose to be taken before bedtime because of its sedative effects. Although quetiapine is approved by the FDA for the treatment of schizophrenia and bipolar disorder, it is frequently prescribed for off-label purposes including insomnia or the treatment of anxiety disorders. Due to its sedative side effects, reports of quetiapine abuse (sometimes by insufflating crushed tablets) have emerged in medical literature; for the same reason, abuse of other antipsychotics, such as chlorpromazine (Thorazine), may occur as well, but research related to the abuse of typical antipsychotics is limited. for the same reason, abuse of other antipsychotics, such as chlorpromazine (Thorazine), may occur as well, but research related to the abuse of typical antipsychotics is limited.
Contaminant Sources
  • FooDB Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amine
  • Antipsychotic Agent
  • Drug
  • Ether
  • Food Toxin
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-[2-(4-Dibenzo[b,F][1,4]thiazepin-11-yl-1-piperazinyl)ethoxy]ethanolChEBI
QuetiapinaChEBI
QuetiapinumChEBI
NorsicKegg
Quetiapine fumarateHMDB
SeroquelHMDB
Ethanol, 2-(2-(4-dibenzo(b,F)(1,4)thiazepin-11-yl-1-piperazinyl)ethoxy)-, (e)-2-butenedioate (2:1) (salt)HMDB
Fumarate, quetiapineHMDB
2-(2-(4-Dibenzo(b,F)(1,4)thiazepine-11-yl-1-piperazinyl)ethoxy)ethanolHMDB
Chemical FormulaC21H25N3O2S
Average Molecular Mass383.507 g/mol
Monoisotopic Mass383.167 g/mol
CAS Registry Number111974-69-7
IUPAC Name2-[2-(4-{2-thia-9-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,9,11,13-heptaen-10-yl}piperazin-1-yl)ethoxy]ethan-1-ol
Traditional Namequetiapine
SMILESOCCOCCN1CCN(CC1)C1=NC2=CC=CC=C2SC2=CC=CC=C12
InChI IdentifierInChI=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
InChI KeyURKOMYMAXPYINW-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dibenzothiazepines. Dibenzothiazepines are compounds containing a dibenzothiazepine moiety, which consists of two benzene connected by a thiazepine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzothiazepines
Sub ClassDibenzothiazepines
Direct ParentDibenzothiazepines
Alternative Parents
Substituents
  • Dibenzothiazepine
  • Diarylthioether
  • Aryl thioether
  • N-alkylpiperazine
  • 1,4-diazinane
  • Piperazine
  • Benzenoid
  • Imidolactam
  • Tertiary amine
  • Tertiary aliphatic amine
  • Azacycle
  • Carboxylic acid amidine
  • Dialkyl ether
  • Ether
  • Amidine
  • Organic 1,3-dipolar compound
  • Thioether
  • Propargyl-type 1,3-dipolar organic compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Organic nitrogen compound
  • Organic oxygen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue Locations
  • Brain
  • Liver
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceSolid (1).
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityModerate
Predicted Properties
PropertyValueSource
Water Solubility0.04 g/LALOGPS
logP2.93ALOGPS
logP2.81ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)15.12ChemAxon
pKa (Strongest Basic)7.06ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area48.3 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity114.09 m³·mol⁻¹ChemAxon
Polarizability42.78 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0007-9264000000-4758f7f7f4947282ccbbSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fdo-9543200000-188eddba94dd2a57f908Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-001i-0039000000-6e58caa07d6f7951f23eSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001i-0089000000-b7b1c7d0bf6bb604c5cbSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0uk9-1390000000-ce855b6e08dee583681bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0ul0-0092000000-b8ad82fb58fb41b6f4faSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0019000000-380bdfab40abc4fe9104Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00e9-2019000000-9a9f0ea1ddcfe3e51fbaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-6942000000-82ff888287705b61f40dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1039000000-026ca51b770ab0fc287dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001l-2019000000-503cee9b3e7cc04ade6aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08fu-9710000000-457979a8d0088bdeade2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0009000000-e07800842abb48579469Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000x-0019000000-f62857d5511d39f2c201Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0w29-0191000000-5ce92b5e3a22486cc2f2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1009000000-74ca90c52d883a3f4f25Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-9027000000-059f5ab035332d4b8f68Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01p6-2192000000-1ea11b461430b2f762a1Spectrum
Toxicity Profile
Route of ExposureInhalation (MSDS, A308); ingestion (MSDS, A308); dermal (MSDS, A308) Rapidly and well absorbed.
Mechanism of ToxicityThe mechanism of action of quetiapine, as with other drugs used to treat schizophrenia, is unknown. However, it is thought that the drug's therapeutic activity in schizophrenia is mediated through a combination of dopamine type 2 (D2) and serotonin type 2 (5HT2) receptor antagonism. Although quetiapine is known to bind other receptors with similar affinity, only the dopamine D2 and serotonin 5HT2 receptor binding is responsible for quetiapine's therapeutic activity in schizophrenia.
MetabolismHepatic. 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 ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesQuetiapine is indicated for the treatment of schizophrenia, depressive episodes associated with bipolar disorder, acute manic episodes associated with bipolar I disorder, and maintenance treatment of bipolar I disorder (12).
Minimum Risk LevelNot Available
Health EffectsTachycardia, development of tardive dyskinesia, an incurable neurological disorder, and a neuroleptic malignant syndrome may result from use or overdose of Quetiapine (12).
SymptomsSymptoms of overdose include drowsiness and sedation, tachycardia, and hypotension.
TreatmentThere is no specific antidote. Treat quinidine-like cardiotoxic effects with bicarbonate. Maintain an open airway and assist ventilation if necessary. Administer supplemental oxygen. (11)
Concentrations
Not Available
DrugBank IDDB01224
HMDB IDHMDB0005021
FooDB IDFDB023592
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkQuetiapine
Chemspider ID4827
ChEBI ID8707
PubChem Compound ID5002
Kegg Compound IDC07397
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

DrugSyn.org

MSDSLink
General References
1. Bozsing, Daniel; Kovanyine, Lax Gyoergyi; Simig, Gyula; Rakoczy, Gyoergyne; Toempe, Peter; Krasznai, Gyoergy; Vereczkeyne, Donath Gyoergyi; Nagy, Kalman. A process for the preparation of quetiapine and its intermediates. 2001, Patent WO2001055125A1 (https://patents.google.com/patent/WO2001055125A1/en)
2. Parker DR, McIntyre IM: Case studies of postmortem quetiapine: therapeutic or toxic concentrations? J Anal Toxicol. 2005 Jul-Aug;29(5):407-12.
3. Stip E, Fahim C, Mancini-Marie A, Bentaleb LA, Mensour B, Mendrek A, Beauregard M: Restoration of frontal activation during a treatment with quetiapine: an fMRI study of blunted affect in schizophrenia. Prog Neuropsychopharmacol Biol Psychiatry. 2005 Jan;29(1):21-6. Epub 2004 Nov 5.
4. Langman LJ, Kaliciak HA, Carlyle S: Fatal overdoses associated with quetiapine. J Anal Toxicol. 2004 Sep;28(6):520-5.
5. Stephan PL, Jaquenoud Sirot E, Mueller B, Eap CB, Baumann P: Adverse drug reactions following nonresponse in a depressed patient with CYP2D6 deficiency and low CYP 3A4/5 activity. Pharmacopsychiatry. 2006 Jul;39(4):150-2.
6. Fahim C, Stip E, Mancini-Marie A, Gendron A, Mensour B, Beauregard M: Differential hemodynamic brain activity in schizophrenia patients with blunted affect during quetiapine treatment. J Clin Psychopharmacol. 2005 Aug;25(4):367-71.