Risperidone (CHEM002259)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (32)XML
Record Information
Version1.0
Creation Date2009-07-21 20:27:30 UTC
Update Date2026-05-14 16:47:24 UTC
Accession NumberCHEM002259
Identification
Common NameRisperidone
ClassSmall Molecule
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.
Contaminant Sources
  • FooDB Chemicals
  • STOFF IDENT Compounds
  • Suspected Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amine
  • Antipsychotic Agent
  • Dopamine Antagonist
  • Drug
  • Ester
  • Food Toxin
  • Human Neurotoxin
  • Metabolite
  • Organic Compound
  • Organofluoride
  • Serotonin Antagonist
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
RisperdalChEBI
RisperidonaChEBI
RisperidonumChEBI
RisperinChEBI
RispoleptChEBI
RispolinChEBI
SequinanChEBI
BelivonHMDB
BuspironeHMDB
RispenHMDB
Risperdal m-tabHMDB
SpironHMDB
Consta, risperdalHMDB
Risperdal constaHMDB
RisperidalHMDB
Chemical FormulaC23H27FN4O2
Average Molecular Mass410.485 g/mol
Monoisotopic Mass410.212 g/mol
CAS Registry Number106266-06-2
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 Namerisperidone
SMILESCC1=C(CCN2CCC(CC2)C2=NOC3=C2C=CC(F)=C3)C(=O)N2CCCCC2=N1
InChI IdentifierInChI=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
Description belongs to the class of organic compounds known as pyridopyrimidines. Pyridopyrimidines are compounds containing a pyridopyrimidine, which consists of a pyridine fused to a pyrimidine. Pyridine is 6-membered ring consisting of five carbon atoms and a nitrogen atom. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridopyrimidines
Sub ClassNot Available
Direct ParentPyridopyrimidines
Alternative Parents
Substituents
  • Pyridopyrimidine
  • Benzisoxazole
  • Aralkylamine
  • Pyrimidone
  • Aryl fluoride
  • Aryl halide
  • Piperidine
  • Pyridine
  • Benzenoid
  • Pyrimidine
  • Azole
  • Isoxazole
  • Heteroaromatic compound
  • Lactam
  • Tertiary aliphatic amine
  • Tertiary amine
  • Oxacycle
  • Azacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical Roles
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point170°C
Boiling PointNot Available
Solubility2.8mg/L
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 Area61.94 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity114.55 m³·mol⁻¹ChemAxon
Polarizability45.27 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-003r-3943000000-ac9dc593f66de665b41fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0000900000-b0fe7f692a00657a0970Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03dl-0800900000-4e0f5ed855c5bb92c98fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-01ox-0900600000-8473cdb789508bd753a4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-0900000000-3d06f3ad1210b9482139Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-0900000000-d0dcf9d7f61a2c2bc652Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-0000900000-dde599ea867efca2809bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0006-0900300000-9a423e6e6775ee918924Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0006-0900000000-b3a1059a8514321aac84Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0006-0900000000-3160d58bf1d154a8d21cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0006-2900000000-530259828e362c7f2a3cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-02u3-8900000000-c5ae8612478a7ea315c0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-066r-9200000000-466435c830554a2d51eaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-066r-9100000000-352e00f2fbc78e81df2cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-066r-9000000000-de0b42c9894812c69015Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03dl-1901800000-c9a45676bc3a1d1829b7Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4i-2980000000-3574e0025348c64db6fcSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03dl-0900800000-6edaf8e46040d5648f3fSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4i-0790000000-e0be2a4dba2d14313d6cSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0006-2900000000-81e94f588db0cd3c9ea8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0101900000-3b466daa9c41370f4854Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-007o-3691300000-55512c8d0bd8674ec200Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-4911000000-3a317742f6b195590ad6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0100900000-07ab322b943804185f19Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aor-0963800000-9bd0f93b2f4ad45645c8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-1981000000-05e48d9b8d09b65bf664Spectrum
Toxicity Profile
Route of ExposureWell absorbed. The absolute oral bioavailability of risperidone is 70% (CV=25%). The relative oral bioavailability of risperidone from a tablet is 94% (CV=10%) when compared to a solution.
Mechanism of ToxicityBlockade of dopaminergic D2 receptors in the limbic system alleviates positive symptoms of schizophrenia such as hallucinations, delusions, and erratic behavior and speech. Blockade of serotonergic 5-HT2 receptors in the mesocortical tract, causes an excess of dopamine and an increase in dopamine transmission, resulting in an increase in dopamine transmission and an elimination of core negative symptoms. Dopamine receptors in the nigrostriatal pathway are not affected by risperidone and extrapyramidal effects are avoided. Like other 5-HT2 antagonists, risperidone also binds at alpha(1)-adrenergic receptors and, to a lesser extent, at histamine H1 and alpha(2)-adrenergic receptors.
MetabolismExtensively metabolized by hepatic cytochrome P450 2D6 isozyme to 9-hydroxyrisperidone, which has approximately the same receptor binding affinity as risperidone. Hydroxylation is dependent on debrisoquine 4-hydroxylase and metabolism is sensitive to genetic polymorphisms in debrisoquine 4-hydroxylase. Risperidone also undergoes N-dealkylation to a lesser extent. Route of Elimination: Risperidone is extensively metabolized in the liver.In healthy elderly subjects, renal clearance of both risperidone and 9-hydroxyrisperidone was decreased, and elimination half-lives were prolonged compared to young healthy subjects. Half Life: 20-24 hours
Toxicity ValuesLD50=82.1mg/kg (orally in mice).
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the treatment of schizophrenia in adults and in adolescents, ages 13 to 17, and for the short-term treatment of manic or mixed episodes of bipolar I disorder in children and adolescents ages 10 to 17. May also be used to manage symptoms of inappropriate behavior due to aggression and/or psychosis in patients with severe dementia.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsSymptoms of overdose include drowsiness, sedation, tachycardia, hypotension, and extrapyramidal symptoms.
TreatmentIn case of acute overdosage, establish and maintain an airway and ensure adequate oxygenation and ventilation. Gastric lavage (after intubation, if patient is unconscious) and administration of activated charcoal together with a laxative should be considered. The possibility of obtundation, seizures, or dystonic reaction of the head and neck following overdose may create a risk of aspiration with induced emesis. Cardiovascular monitoring should commence immediately and should include continuous electrocardiographic monitoring to detect possible arrhythmias. If antiarrhythmic therapy is administered, disopyramide, procainamide, and quinidine carry a theoretical hazard of QT-prolonging effects that might be additive to those of risperidone. Similarly, it is reasonable to expect that the alpha-blocking properties of bretylium might be additive to those of risperidone, resulting in problematic hypotension. There is no specific antidote to Risperidone. (9)
Concentrations
Not Available
DrugBank IDDB00734
HMDB IDHMDB0005020
FooDB IDFDB023591
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID2348
PDB IDNot Available
Wikipedia LinkRisperidone
Chemspider ID4895
ChEBI ID8871
PubChem Compound ID5073
Kegg Compound IDC06861
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

DrugSyn.org

MSDSLink
General References
1. 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
2. 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
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=11229618
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=11476125
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=14687852
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=14728058
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=15096074
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=17054229
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=18545060
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=18722468
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=19412457
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=20825390
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=23327578