SynCED: Risperidone

Record Information

Version

1.0

Creation Date

2009-07-21 20:27:30 UTC

Update Date

2026-05-14 16:47:24 UTC

Accession Number

CHEM002259

Identification

Common Name

Risperidone

Class

Small Molecule

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.

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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Risperdal	ChEBI
Risperidona	ChEBI
Risperidonum	ChEBI
Risperin	ChEBI
Rispolept	ChEBI
Rispolin	ChEBI
Sequinan	ChEBI
Belivon	HMDB
Buspirone	HMDB
Rispen	HMDB
Risperdal m-tab	HMDB
Spiron	HMDB
Consta, risperdal	HMDB
Risperdal consta	HMDB
Risperidal	HMDB

Chemical Formula

C₂₃H₂₇FN₄O₂

Average Molecular Mass

410.485 g/mol

Monoisotopic Mass

410.212 g/mol

CAS Registry Number

106266-06-2

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 Name

risperidone

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

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridopyrimidines

Sub Class

Not Available

Direct Parent

Pyridopyrimidines

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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

organofluorine compound (CHEBI:8871 )
pyridopyrimidine (CHEBI:8871 )
1,2-benzoxazoles (CHEBI:8871 )
heteroarylpiperidine (CHEBI:8871 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

Chemical Roles

EC 3.4.21.26 (prolyl oligopeptidase) inhibitor

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	170°C
Boiling Point	Not Available
Solubility	2.8mg/L

Predicted Properties

Property	Value	Source
Water Solubility	0.17 g/L	ALOGPS
logP	3.27	ALOGPS
logP	2.63	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Basic)	8.76	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	61.94 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	114.55 m³·mol⁻¹	ChemAxon
Polarizability	45.27 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Toxicity Profile

Route of Exposure

Well 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 Toxicity

Blockade 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.

Metabolism

Extensively 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 Values

LD₅₀=82.1mg/kg (orally in mice).

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For 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 Level

Not Available

Health Effects

Not Available

Symptoms

Symptoms of overdose include drowsiness, sedation, tachycardia, hypotension, and extrapyramidal symptoms.

Treatment

In 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

External Links

DrugBank ID

DB00734

HMDB ID

HMDB0005020

FooDB ID

FDB023591

Phenol Explorer ID

Not Available

KNApSAcK ID