Human Metabolome Database Version 3.5

Showing metabocard for Quetiapine (HMDB05021)

Record Information
Version 3.5
Creation Date 2006-10-17 03:02:18 -0600
Update Date 2013-02-08 17:13:47 -0700
HMDB ID HMDB05021
Secondary Accession Numbers None
Metabolite Identification
Common Name Quetiapine
Description 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; 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Quetiapine fumarate
  2. Seroquel
Chemical Formula C21H25N3O2S
Average Molecular Weight 383.507
Monoisotopic Molecular Weight 383.166747749
IUPAC Name 2-[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 Name quetiapine
CAS Registry Number 111974-69-7
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 Key URKOMYMAXPYINW-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Benzothiazepines
Sub Class Dibenzothiazepines
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 Parent Dibenzothiazepines
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.04 g/L ALOGPS
LogP 2.93 ALOGPS
LogP 2.81 ChemAxon
LogS -3.98 ALOGPS
pKa (strongest acidic) 15.12 ChemAxon
pKa (strongest basic) 7.06 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 48.3 A2 ChemAxon
Rotatable Bond Count 5 ChemAxon
Refractivity 114.09 ChemAxon
Polarizability 42.62 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue Location
  • Liver
  • Brain
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 20.7 (1.04-198.0) uM Adult (>18 years old) Both Quetiapine poisoning
Cerebrospinal Fluid (CSF) Detected and Quantified 0.0783 (0.00157-0.146) uM Adult (>18 years old) Both schizophrenia (CYP2D6)
Cerebrospinal Fluid (CSF) Detected and Quantified 0.0809 (0.00157-0.146) uM Adult (>18 years old) Not Specified schizophrenia (CYP3A4 rs4646437)
Cerebrospinal Fluid (CSF) Detected and Quantified 0.0626 (0.00157-0.146) uM Adult (>18 years old) Not Specified schizophrenia (CYP3A5)
Cerebrospinal Fluid (CSF) Detected and Quantified 0.0652 (0.00157-0.146) uM Adult (>18 years old) Not Specified schizophrenia (CYP3A7)
Associated Disorders and Diseases
Disease References
Quetiapine poisoning
  • 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 Link_out
      Associated OMIM IDs None
      DrugBank ID Not Available
      DrugBank Metabolite ID Not Available
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB023592
      KNApSAcK ID Not Available
      Chemspider ID 4827 Link_out
      KEGG Compound ID C07397 Link_out
      BioCyc ID Not Available
      BiGG ID Not Available
      Wikipedia Link Quetiapine Link_out
      NuGOwiki Link HMDB05021 Link_out
      Metagene Link HMDB05021 Link_out
      METLIN ID Not Available
      PubChem Compound 5002 Link_out
      PDB ID Not Available
      ChEBI ID 8707 Link_out
      References
      Synthesis Reference 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.
      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 Link_out
      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 Link_out
      3. Langman LJ, Kaliciak HA, Carlyle S: Fatal overdoses associated with quetiapine. J Anal Toxicol. 2004 Sep;28(6):520-5. Pubmed: 15516308 Link_out
      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 Link_out
      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 Link_out

      Enzymes
      Name: Cytochrome P450 3A4
      Reactions: Not Available
      Gene Name: CYP3A4
      Uniprot ID: P08684 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Cytochrome P450 2D6
      Reactions: Not Available
      Gene Name: CYP2D6
      Uniprot ID: P10635 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: D(2) dopamine receptor
      Reactions: Not Available
      Gene Name: DRD2
      Uniprot ID: P14416 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: 5-hydroxytryptamine receptor 2B
      Reactions: Not Available
      Gene Name: HTR2B
      Uniprot ID: P41595 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: 5-hydroxytryptamine receptor 1A
      Reactions: Not Available
      Gene Name: HTR1A
      Uniprot ID: P08908 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: 5-hydroxytryptamine receptor 2A
      Reactions: Not Available
      Gene Name: HTR2A
      Uniprot ID: P28223 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: 5-hydroxytryptamine receptor 2C
      Reactions: Not Available
      Gene Name: HTR2C
      Uniprot ID: P28335 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Histamine H1 receptor
      Reactions: Not Available
      Gene Name: HRH1
      Uniprot ID: P35367 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Alpha-1B adrenergic receptor
      Reactions: Not Available
      Gene Name: ADRA1B
      Uniprot ID: P35368 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: D(1A) dopamine receptor
      Reactions: Not Available
      Gene Name: DRD1
      Uniprot ID: P21728 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA