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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-10-17 09:02:18 UTC
Update Date2017-10-23 19:04:15 UTC
HMDB IDHMDB0005021
Secondary Accession Numbers
  • HMDB05021
Metabolite Identification
Common NameQuetiapine
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.
Structure
Thumb
Synonyms
ValueSource
2-[2-(4-dibenzo[b,F][1,4]Thiazepin-11-yl-1-piperazinyl)ethoxy]ethanolChEBI
QuetiapinaChEBI
QuetiapinumChEBI
Quetiapine fumarateHMDB
SeroquelHMDB
Ethanol, 2-(2-(4-dibenzo(b,F)(1,4)thiazepin-11-yl-1-piperazinyl)ethoxy)-, (e)-2-butenedioate (2:1) (salt)MeSH
Fumarate, quetiapineMeSH
2-(2-(4-dibenzo(b,F)(1,4)Thiazepine-11-yl-1-piperazinyl)ethoxy)ethanolMeSH
Chemical FormulaC21H25N3O2S
Average Molecular Weight383.507
Monoisotopic Molecular Weight383.166747749
IUPAC Name2-[2-(4-{2-thia-9-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,9,11,13-heptaen-10-yl}piperazin-1-yl)ethoxy]ethan-1-ol
Traditional Namequetiapine
CAS Registry Number111974-69-7
SMILES
OCCOCCN1CCN(CC1)C1=NC2=CC=CC=C2SC2=CC=CC=C12
InChI Identifier
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
InChI KeyURKOMYMAXPYINW-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as dibenzothiazepines. These are compounds containing a dibenzothiazepine moiety, which consists of two benzene connected by a thiazepine ring.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassBenzothiazepines
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
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Route of exposure:

  Parenteral:

  Enteral:

Role

Industrial application:

  Pharmaceutical industry:

Indirect biological role:

Physiological effect

Health effect:

  Health condition:

    Vascular disorders:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0007-9264000000-4758f7f7f4947282ccbbView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fdo-9543200000-188eddba94dd2a57f908View in MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-001i-0039000000-6e58caa07d6f7951f23eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001i-0089000000-b7b1c7d0bf6bb604c5cbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0uk9-1390000000-ce855b6e08dee583681bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0019000000-380bdfab40abc4fe9104View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00e9-2019000000-9a9f0ea1ddcfe3e51fbaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-6942000000-82ff888287705b61f40dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1039000000-026ca51b770ab0fc287dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001l-2019000000-503cee9b3e7cc04ade6aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08fu-9710000000-457979a8d0088bdeade2View in MoNA
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue Location
  • Brain
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
Not Available
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified20.7 (1.04-198.0) uMAdult (>18 years old)BothQuetiapine poisoning details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0783 (0.00157-0.146) uMAdult (>18 years old)Bothschizophrenia (CYP2D6) details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0809 (0.00157-0.146) uMAdult (>18 years old)Not Specifiedschizophrenia (CYP3A4 rs4646437) details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0626 (0.00157-0.146) uMAdult (>18 years old)Not Specifiedschizophrenia (CYP3A5) details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0652 (0.00157-0.146) uMAdult (>18 years old)Not Specifiedschizophrenia (CYP3A7) details
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-3 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-1 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease References
Quetiapine poisoning
  1. Flammia DD, Valouch T, Venuti S: Tissue distribution of quetiapine in 20 cases in Virginia. J Anal Toxicol. 2006 May;30(4):287-92. [PubMed:16803670 ]
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023592
KNApSAcK IDNot Available
Chemspider ID4827
KEGG Compound IDC07397
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkQuetiapine
METLIN IDNot Available
PubChem Compound5002
PDB IDNot Available
ChEBI ID8707
References
Synthesis ReferenceBozsing, 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.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Parker DR, McIntyre IM: Case studies of postmortem quetiapine: therapeutic or toxic concentrations? J Anal Toxicol. 2005 Jul-Aug;29(5):407-12. [PubMed:16105271 ]
  2. 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. [PubMed:15610941 ]
  3. Langman LJ, Kaliciak HA, Carlyle S: Fatal overdoses associated with quetiapine. J Anal Toxicol. 2004 Sep;28(6):520-5. [PubMed:15516308 ]
  4. 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. [PubMed:16871470 ]
  5. 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. [PubMed:16012281 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:
DRD2
Uniprot ID:
P14416
Molecular weight:
50618.9
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system
Gene Name:
HTR2B
Uniprot ID:
P41595
Molecular weight:
54297.4
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:
HTR1A
Uniprot ID:
P08908
Molecular weight:
46106.3
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. This receptor is involved in tracheal smooth muscle contraction, bronchoconstriction, and control of aldosterone production
Gene Name:
HTR2A
Uniprot ID:
P28223
Molecular weight:
52602.6
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system
Gene Name:
HTR2C
Uniprot ID:
P28335
Molecular weight:
51820.7
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system
Gene Name:
HRH1
Uniprot ID:
P35367
Molecular weight:
55783.6
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system
Gene Name:
ADRA1B
Uniprot ID:
P35368
Molecular weight:
56835.4
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase
Gene Name:
DRD1
Uniprot ID:
P21728
Molecular weight:
49292.8