RISPERIDONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C23H27FN4O2
Molecular Weight	410.4845
Optical Activity	UNSPECIFIED
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=C(CCN2CCC(CC2)C3=NOC4=C3C=CC(F)=C4)C(=O)N5CCCCC5=N1

InChI

InChIKey=RAPZEAPATHNIPO-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C23H27FN4O2
Molecular Weight	410.4845
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

Risperidone, a benzisoxazole derivative, is an atypical antipsychotic drug with high affinity for 5-hydrotryptamine (5-HT) and dopamine D2 receptors. It is FDA approved for the treatment of schizophrenia, bipolar mania, irritability associated with autistic disorder. Carbamazepine and other enzyme inducers decrease plasma concentrations of risperidone. Vice versa, Fluoxetine, paroxetine, and other CYP 2D6 enzyme inhibitors increase plasma concentrations of risperidone. Common adverse reactions include increased mortality in elderly patients with dementia-related psychosis, cerebrovascular adverse events, including stroke, in elderly patients with dementia-related psychosis, neuroleptic malignant syndrome, tardive dyskinesia , metabolic Changes (hyperglycemia and diabetes mellitus, dyslipidemia, weight gain), hyperprolactinemia, orthostatic hypotension, leukopenia, neutropenia, agranulocytosis, potential for cognitive and motor impairment, seizures, dysphagia, priapism, disruption of body temperature regulation.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serotonin 1d (5-HT1d) receptor 45	Antagonist 2438	Schizophrenia	3.9 nM [Kd]
Adrenergic receptor alpha-1 157	Antagonist 2438	Schizophrenia	2.7 nM [Kd]
Serotonin 2a (5-HT2a) receptor 183	Antagonist 2438	Schizophrenia	0.15 nM [Kd]
Dopamine D2 receptor 270	Antagonist 2438	Schizophrenia	3.8 nM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Schizophrenia 292	Primary	Adrenergic receptor alpha-1 Serotonin 2a (5-HT2a) receptor Serotonin 1d (5-HT1d) receptor Dopamine D2 receptor	Approved 7777	RISPERDAL
Autistic Disorder 10	Primary	Adrenergic receptor alpha-1 Serotonin 2a (5-HT2a) receptor Serotonin 1d (5-HT1d) receptor Dopamine D2 receptor	Approved 7777	RISPERDAL
Bipolar Disorder 98	Primary	Adrenergic receptor alpha-1 Serotonin 2a (5-HT2a) receptor Serotonin 1d (5-HT1d) receptor Dopamine D2 receptor	Approved 7777	RISPERDAL
Anorexia Nervosa 4			Approved (off-label) 7
Borderline personality disorder 1			Approved (off-label) 7
Major depressive disorder 1			Approved (off-label) 7

PubMed

Title	Date	PubMed
Use of the dopamine agonists bromocriptine and cabergoline in the management of risperidone-induced hyperprolactinemia in patients with psychotic disorders.	2000 Dec	11194712
[Neuropsychiatric symptoms in preventive antimalarial treatment with mefloquine: apropos of 2 cases].	2000 Jul-Aug	11064842
Serotonin and dopamine antagonism in obsessive-compulsive disorder: effect of atypical antipsychotic drugs.	2000 Nov	11147933
Risperidone-associated hyperprolactinemia.	2000 Nov-Dec	11155212
Weight change and atypical antipsychotic treatment in patients with schizophrenia.	2001	11232752
Evidence for the effectiveness of olanzapine among patients nonresponsive and/or intolerant to risperidone.	2001	11232749
Antipsychotic medications and the elderly: effects on cognition and implications for use.	2001	11232738
Olanzapine: an updated review of its use in the management of schizophrenia.	2001	11217867
Atypical antipsychotics: new directions and new challenges in the treatment of schizophrenia.	2001	11160792
Novel treatments for bipolar disorder.	2001 Apr	11281816
Protein thiol oxidation by haloperidol results in inhibition of mitochondrial complex I in brain regions: comparison with atypical antipsychotics.	2001 Apr	11222923
Health care utilization in patients with schizophrenia maintained on atypical versus conventional antipsychotics.	2001 Feb	11294482
Dose relationship of limbic-cortical D2-dopamine receptor occupancy with risperidone.	2001 Feb	11292000
Addition of risperidone to clozapine therapy in chronically psychotic inpatients.	2001 Feb	11247102
Priapism associated with polypharmacy.	2001 Feb	11247100
Weight gain with risperidone among patients with mental retardation: effect of calorie restriction.	2001 Feb	11247096
Long-term treatment of chronic schizophrenia with risperidone: a study with plasma levels.	2001 Feb	11246293
Drug induced akathisia, suicidal ideation and its treatment in the elderly.	2001 Feb	11241732
Tolerability and effectiveness of atypical antipsychotics in male geriatric inpatients.	2001 Feb	11241729
Combination risperidone and quetiapine therapy in refractory schizophrenia.	2001 Feb	11221496
A case of risperidone-induced stuttering.	2001 Feb	11199937
Atypical antipsychotics and cardiovascular risk in schizophrenic patients.	2001 Feb	11199934
Adverse drug interaction between risperidone and carbamazepine in a patient with chronic schizophrenia and deficient CYP2D6 activity.	2001 Feb	11199933
Rehospitalization rates of chronically ill schizophrenic patients discharged on a regimen of risperidone, olanzapine, or conventional antipsychotics.	2001 Feb	11156809
Hyperthermia and chronic pancerebellar syndrome after cocaine abuse.	2001 Feb 26	11252123
Receptor-mediated regulation of serotonin output in the rat dorsal raphe nucleus: effects of risperidone.	2001 Jan	11271402
Risperidone versus pimozide in Tourette's disorder: a comparative double-blind parallel-group study.	2001 Jan	11235929
Acute and long-term treatment of catatonia with risperidone.	2001 Jan	11229618
Bodyweight gain with atypical antipsychotics. A comparative review.	2001 Jan	11219487
Risperidone-induced cholestatic hepatitis.	2001 Jan	11204814
Does risperidone have a place in the treatment of nonschizophrenic patients?	2001 Jan	11195255
Clozapine therapy for a patient with a history of Hodgkin's disease.	2001 Jan	11141545
Relationship between plasma risperidone and 9-hydroxyrisperidone concentrations and clinical response in patients with schizophrenia.	2001 Jan 1	11205425
Consistency of atypical antipsychotic superiority to placebo in recent clinical trials.	2001 Jan 1	11163781
Dopamine transporter density in young patients with schizophrenia assessed with [123]FP-CIT SPECT.	2001 Jan 15	11163545
Hyperfunction of dopaminergic and serotonergic neuronal systems in mice lacking the NMDA receptor epsilon1 subunit.	2001 Jan 15	11160454
Antipsychotic drugs classified by their effects on the release of dopamine and noradrenaline in the prefrontal cortex and striatum.	2001 Jan 26	11165224
[Viewpoint of schizophrenic patients: a European survey].	2001 Jan-Feb	11294036
Effects of dopamine antagonists with different receptor blockade profiles on morphine-induced place preference in male mice.	2001 Jun	11275296
Effectiveness of ECT combined with risperidone against aggression in schizophrenia.	2001 Mar	11281510
Suspected induction of a pyoderma gangrenosum-like eruption due to sulpiride treatment.	2001 Mar	11270303
5-HT(2A) and D(2) receptor blockade increases cortical DA release via 5-HT(1A) receptor activation: a possible mechanism of atypical antipsychotic-induced cortical dopamine release.	2001 Mar	11238736
Fixed-dosed risperidone in mania: an open experimental trial.	2001 Mar	11236068
Does fast dissociation from the dopamine d(2) receptor explain the action of atypical antipsychotics?: A new hypothesis.	2001 Mar	11229973
Pharmacological characterization of locomotor sensitization induced by chronic phencyclidine administration.	2001 Mar	11181923
Estrogen - a potential treatment for schizophrenia.	2001 Mar 1	11278160
Effects of olanzapine and other antipsychotics on cognitive function in chronic schizophrenia: a longitudinal study.	2001 Mar 1	11278151
Short-term inpatient pharmacotherapy of schizophrenia.	2001 May-Jun	11287404
Risperidone addition and psychotic exacerbation.	2001 Winter	11207341
Full remission of panic attacks in a schizophrenic patient after switching from haloperidol to risperidone.	2001 Winter	11207340

Patents

Sample Use Guides

In Vivo Use Guide

Initial dosing is generally 2 mg/day. Dose increases should then occur at intervals not less than 24 hours, in increments of 1–2 mg/day, as tolerated, to a recommended dose of 4–8 mg/day. Effective dose range - 0.5-16 mg (disease dependent).

Route of Administration: Intramuscular; Oral

In Vitro Use Guide

Measurement of ATP contents in the neuronal cell line showed significantly increased levels after a 24-h treatment with 25 microg/mL risperidone.

Substance Class	Chemical Created by `admin` on `Tue Oct 22 00:15:49 UTC 2019` Edited by `admin` on `Tue Oct 22 00:15:49 UTC 2019`
Record UNII	L6UH7ZF8HC
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

RISPERIDONE

Official Name

English

R-64766

Code

English

R 64 766

Code

English

RISPERIDONE [WHO-DD]

Common Name

English

RISPERIDONE [USAN]

Common Name

English

N05AX08

Code

English

RISPERIDONE [ORANGE BOOK]

Common Name

English

R-64,766

Code

English

PERSERIS

Brand Name

English

RISPERIDONE [HSDB]

Common Name

English

LY03004

Code

English

RISPERIDONE [USP-RS]

Common Name

English

RISPERIDONE [MART.]

Common Name

English

RCN3028

Code

English

RISPERDAL

Brand Name

English

RCN-3028

Code

English

RISPERIDONE [JAN]

Common Name

English

3-(2-(4-(6-FLUORO-1,2-BENZISOXAZOL-3-YL)-1-PIPERIDINYL)ETHYL)-6,7,8,9-TETRAHYDRO-2-METHYL-4H-PYRIDO(1,2-A)PYRIMIDIN-4-ONE

Systematic Name

English

R-64-766

Code

English

RISPERIDONE [EP]

Common Name

English

LY-03004

Code

English

RISPERIDONE [INN]

Common Name

English

RISPERIDONE [USP]

Common Name

English

4H-PYRIDO(1,2-A)PYRIMIDIN-4-ONE, 3-(2-(4-(6-FLUORO-1,2-BENZISOXAZOL-3-YL)-1-PIPERIDINYL)ETHYL)-6,7,8,9-TETRAHYDRO-2-METHYL-

Systematic Name

English

RISPERIDONE [VANDF]

Common Name

English

RISPERIDONE [MI]

Common Name

English

Classification Tree Code System Code

WHO-ATC

N05AX08