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Record Information
Version3.6
Creation Date2006-10-17 09:02:18 UTC
Update Date2013-02-09 00:13:47 UTC
HMDB IDHMDB05021
Secondary Accession NumbersNone
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
  1. Quetiapine fumarate
  2. Seroquel
Chemical FormulaC21H25N3O2S
Average Molecular Weight383.507
Monoisotopic Molecular Weight383.166747749
IUPAC Name2-[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
Traditional IUPAC 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
KingdomOrganic Compounds
Super ClassAromatic Heteropolycyclic Compounds
ClassBenzothiazepines
Sub ClassDibenzothiazepines
Other Descriptors
  • N-alkylpiperazine(ChEBI)
  • N-arylpiperazine(ChEBI)
  • Organic Compounds
  • dibenzothiazepine(ChEBI)
Substituents
  • Carboxylic Acid Amidine
  • Dialkyl Ether
  • Para Thiazepine
  • Piperazine
  • Primary Alcohol
  • Tertiary Aliphatic Amine (Trialkylamine)
  • Thioether
Direct ParentDibenzothiazepines
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
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 area48.3ChemAxon
rotatable bond count5ChemAxon
refractivity114.09ChemAxon
polarizability42.62ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue Location
  • Brain
  • Liver
PathwaysNot Available
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
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
NuGOwiki LinkHMDB05021
Metagene LinkHMDB05021
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