Human Metabolome Database Version 3.5

Showing metabocard for Risperidone (HMDB05020)

Record Information
Version 3.5
Creation Date 2006-10-17 02:56:49 -0600
Update Date 2013-02-08 17:13:47 -0700
HMDB ID HMDB05020
Secondary Accession Numbers None
Metabolite Identification
Common Name Risperidone
Description Risperidone is an atypical antipsychotic medication approved in 1993. It is most often used to treat delusional psychosis (including schizophrenia), but risperidone (like other atypical antipsychotics) is also used to treat some forms of bipolar disorder, psychotic depression and Tourette syndrome. Generally lower doses are used for autistic spectrum disorders than are used for schizophrenia and other forms of psychosis; Risperidone is a very strong dopamine blocker (antagonist); Risperidone is a very strong dopamine blocker (antagonist); i.e., it inhibits functioning of postsynaptic dopamine receptors. An anxiolytic agent and a serotonin receptor agonist belonging to the azaspirodecanedione class of compounds. Its structure is unrelated to those of the benzodiazepines, but it has an efficacy comparable to diazepam; i.e., it inhibits functioning of postsynaptic dopamine receptors. Risperidone (Belivon, Rispen, Risperdal; in the United States) is an atypical antipsychotic medication. It was approved by the United States Food and Drug Administration (FDA) in 1993. It is most often used to treat delusional psychosis (including schizophrenia), but risperidone (like other atypical antipsychotics) is also used to treat some forms of bipolar disorder, psychotic depression and Tourette syndrome; risperidone has received approval from the Food and Drug Administration (FDA) for symptomatic treatment of irritability in autistic children and adolescents. Risperidone is now the most commonly prescribed antipsychotic medication in the United States.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Belivon
  2. Buspirone
  3. Rispen
  4. Risperdal
  5. Risperdal M-Tab
  6. Risperidone
  7. Spiron
Chemical Formula C23H27FN4O2
Average Molecular Weight 410.4845
Monoisotopic Molecular Weight 410.211804333
IUPAC Name 3-{2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl}-2-methyl-4H,6H,7H,8H,9H-pyrido[1,2-a]pyrimidin-4-one
Traditional IUPAC Name risperidone
CAS Registry Number 106266-06-2
SMILES CC1=C(CCN2CCC(CC2)C2=NOC3=C2C=CC(F)=C3)C(=O)N2CCCCC2=N1
InChI Identifier InChI=1S/C23H27FN4O2/c1-15-18(23(29)28-10-3-2-4-21(28)25-15)9-13-27-11-7-16(8-12-27)22-19-6-5-17(24)14-20(19)30-26-22/h5-6,14,16H,2-4,7-13H2,1H3
InChI Key RAPZEAPATHNIPO-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Pyridopyrimidines
Sub Class N/A
Other Descriptors
  • 1,2-benzoxazoles(ChEBI)
  • cyclic pseudoketone(ChEBI)
  • heteroarylpiperidine(ChEBI)
  • organofluorine compound(ChEBI)
  • pyridopyrimidine(ChEBI)
Substituents
  • Aryl Fluoride
  • Fluorobenzene
  • Isoxazole
  • Organofluoride
  • Oxazole
  • Piperidine
  • Pyridine
  • Pyrimidine
  • Pyrimidone
  • Tertiary Aliphatic Amine (Trialkylamine)
Direct Parent Pyridopyrimidines
Ontology
Status Expected and Not 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 170 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
LogP 3.27 ALOGPS
LogP 2.63 ChemAxon
LogS -3.38 ALOGPS
pKa (strongest basic) 8.76 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 61.94 A2 ChemAxon
Rotatable Bond Count 4 ChemAxon
Refractivity 114.55 ChemAxon
Polarizability 44.91 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
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 FDB023591
KNApSAcK ID Not Available
Chemspider ID 4895 Link_out
KEGG Compound ID C06861 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Risperidone Link_out
NuGOwiki Link HMDB05020 Link_out
Metagene Link HMDB05020 Link_out
METLIN ID 2348 Link_out
PubChem Compound 5073 Link_out
PDB ID Not Available
ChEBI ID 8871 Link_out
References
Synthesis Reference Kennis, Ludo Edmond Josephine; Vandenberk, Jan. Preparation of 1,2-benzisoxazol-3-yl and 1,2-benzisothiazol-3-yl derivatives as antipsychotics. Eur. Pat. Appl. (1986), 33 pp. CODEN: EPXXDW EP 196132 A2 19861001 CAN 106:67292 AN 1987:67292
Material Safety Data Sheet (MSDS) Download (PDF)
General References Not Available

Enzymes
Name: Cytochrome P450 2D6
Reactions: Not Available
Gene Name: CYP2D6
Uniprot ID: P10635 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Beta-1 adrenergic receptor
Reactions: Not Available
Gene Name: ADRB1
Uniprot ID: P08588 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 2A
Reactions: Not Available
Gene Name: HTR2A
Uniprot ID: P28223 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-1A adrenergic receptor
Reactions: Not Available
Gene Name: ADRA1A
Uniprot ID: P35348 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