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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-10-17 08:56:49 UTC
Update Date2022-03-07 02:49:25 UTC
HMDB IDHMDB0005020
Secondary Accession Numbers
  • HMDB05020
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
Data?1582752340
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 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 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
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
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point170 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM205.530932474
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+201.1830932474
DeepCCS[M-H]-198.82230932474
DeepCCS[M-2H]-232.93630932474
DeepCCS[M+Na]+208.26330932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
RisperidoneCC1=C(CCN2CCC(CC2)C2=NOC3=C2C=CC(F)=C3)C(=O)N2CCCCC2=N13744.2Standard polar33892256
RisperidoneCC1=C(CCN2CCC(CC2)C2=NOC3=C2C=CC(F)=C3)C(=O)N2CCCCC2=N13368.5Standard non polar33892256
RisperidoneCC1=C(CCN2CCC(CC2)C2=NOC3=C2C=CC(F)=C3)C(=O)N2CCCCC2=N13589.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Risperidone GC-MS (Non-derivatized) - 70eV, Positivesplash10-003r-3943000000-ac9dc593f66de665b41f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Risperidone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Risperidone LC-ESI-QTOF , positive-QTOFsplash10-03di-0000900000-b0fe7f692a00657a09702017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Risperidone LC-ESI-QTOF , positive-QTOFsplash10-03dl-0800900000-4e0f5ed855c5bb92c98f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Risperidone LC-ESI-QTOF , positive-QTOFsplash10-01ox-0900600000-8473cdb789508bd753a42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Risperidone LC-ESI-QTOF , positive-QTOFsplash10-0006-0900000000-3d06f3ad1210b94821392017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Risperidone LC-ESI-QTOF , positive-QTOFsplash10-0006-0900000000-d0dcf9d7f61a2c2bc6522017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Risperidone LC-ESI-QFT , positive-QTOFsplash10-03di-0000900000-dde599ea867efca2809b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Risperidone LC-ESI-QFT , positive-QTOFsplash10-0006-0900300000-9a423e6e6775ee9189242017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Risperidone LC-ESI-QFT , positive-QTOFsplash10-0006-0900000000-b3a1059a8514321aac842017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Risperidone LC-ESI-QFT , positive-QTOFsplash10-0006-0900000000-3160d58bf1d154a8d21c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Risperidone LC-ESI-QFT , positive-QTOFsplash10-0006-2900000000-530259828e362c7f2a3c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Risperidone LC-ESI-QFT , positive-QTOFsplash10-02u3-8900000000-c5ae8612478a7ea315c02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Risperidone LC-ESI-QFT , positive-QTOFsplash10-066r-9200000000-466435c830554a2d51ea2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Risperidone LC-ESI-QFT , positive-QTOFsplash10-066r-9100000000-352e00f2fbc78e81df2c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Risperidone LC-ESI-QFT , positive-QTOFsplash10-066r-9000000000-de0b42c9894812c690152017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Risperidone , positive-QTOFsplash10-03dl-1901800000-c9a45676bc3a1d1829b72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Risperidone , positive-QTOFsplash10-0a4i-2980000000-3574e0025348c64db6fc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Risperidone , positive-QTOFsplash10-03dl-0900800000-6edaf8e46040d5648f3f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Risperidone , positive-QTOFsplash10-0a4i-0790000000-e0be2a4dba2d14313d6c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Risperidone , positive-QTOFsplash10-0006-2900000000-81e94f588db0cd3c9ea82017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Risperidone 10V, Positive-QTOFsplash10-03di-0101900000-3b466daa9c41370f48542016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Risperidone 20V, Positive-QTOFsplash10-007o-3691300000-55512c8d0bd8674ec2002016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Risperidone 40V, Positive-QTOFsplash10-0006-4911000000-3a317742f6b195590ad62016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Risperidone 10V, Negative-QTOFsplash10-0a4i-0100900000-07ab322b943804185f192016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Risperidone 20V, Negative-QTOFsplash10-0aor-0963800000-9bd0f93b2f4ad45645c82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Risperidone 40V, Negative-QTOFsplash10-014i-1981000000-05e48d9b8d09b65bf6642016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00734
Phenol Explorer Compound IDNot Available
FooDB IDFDB023591
KNApSAcK IDNot Available
Chemspider ID4895
KEGG Compound IDC06861
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkRisperidone
METLIN ID2348
PubChem Compound5073
PDB IDNot Available
ChEBI ID8871
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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)Download (PDF)
General ReferencesNot Available

Enzymes

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:
Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately equal affinity
Gene Name:
ADRB1
Uniprot ID:
P08588
Molecular weight:
51322.1
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. 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:
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. Its effect is mediated by G(q) and G(11) proteins
Gene Name:
ADRA1A
Uniprot ID:
P35348
Molecular weight:
51486.0
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