Record Information
Version3.6
Creation Date2006-10-17 08:56:49 UTC
Update Date2013-02-09 00:13:47 UTC
HMDB IDHMDB05020
Secondary Accession NumbersNone
Metabolite Identification
Common NameRisperidone
DescriptionRisperidone 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
Synonyms
  1. Belivon
  2. Buspirone
  3. Rispen
  4. Risperdal
  5. Risperdal M-Tab
  6. Risperidone
  7. Spiron
Chemical FormulaC23H27FN4O2
Average Molecular Weight410.4845
Monoisotopic Molecular Weight410.211804333
IUPAC Name3-{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 Namerisperidone
CAS Registry Number106266-06-2
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 KeyRAPZEAPATHNIPO-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Heteropolycyclic Compounds
ClassPyridopyrimidines
Sub ClassN/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 ParentPyridopyrimidines
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point170 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility0.17 g/LALOGPS
logP3.27ALOGPS
logP2.63ChemAxon
logS-3.4ALOGPS
pKa (strongest basic)8.76ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count4ChemAxon
hydrogen donor count0ChemAxon
polar surface area61.94ChemAxon
rotatable bond count4ChemAxon
refractivity114.55ChemAxon
polarizability44.91ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023591
KNApSAcK IDNot Available
Chemspider ID4895
KEGG Compound IDC06861
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkRisperidone
NuGOwiki LinkHMDB05020
Metagene LinkHMDB05020
METLIN ID2348
PubChem Compound5073
PDB IDNot Available
ChEBI ID8871
References
Synthesis ReferenceKennis, 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)Not Available
General ReferencesNot Available

Enzymes

Gene Name:
CYP2D6
Uniprot ID:
P10635
Gene Name:
ADRB1
Uniprot ID:
P08588
Gene Name:
DRD2
Uniprot ID:
P14416
Gene Name:
HTR2A
Uniprot ID:
P28223
Gene Name:
HRH1
Uniprot ID:
P35367
Gene Name:
ADRA1A
Uniprot ID:
P35348
Gene Name:
ADRA1B
Uniprot ID:
P35368