OCAPERIDONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C24H25FN4O2
Molecular Weight	420.4793
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CC=CN2C(=O)C(CCN3CCC(CC3)C4=NOC5=C4C=CC(F)=C5)=C(C)N=C12

InChI

InChIKey=ZZQNEJILGNNOEP-UHFFFAOYSA-N

InChI=1S/C24H25FN4O2/c1-15-4-3-10-29-23(15)26-16(2)19(24(29)30)9-13-28-11-7-17(8-12-28)22-20-6-5-18(25)14-21(20)31-27-22/h3-6,10,14,17H,7-9,11-13H2,1-2H3

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Description
Sources: https://adisinsight.springer.com/drugs/800001114 | https://www.drugbank.ca/drugs/DB06229

Ocaperidone [R 79598] is an equipotent antagonist of central dopamine D2 and serotonin2 receptors being investigated as a potential antipsychotic agent. Ocaperidone is a benzisoxazol piperidine antipsychotic primarily binds and with high affinity to 5-HT2 (serotonin) receptors, alpha1 and alpha 2 adrenergic receptors, dopamine D2 receptors and histamine H1 receptors. Ocaperidone is an antagonist primarily at the 5HT and D2 receptors. A proposed mechanism of action is the central D2 receptor blockade which is common to all neuroleptics that are used to treat positive symptoms of schizophrenia.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Dopamine D2 receptor 297 Target ID: CHEMBL217 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11522469	Antagonist 2778	9.52 null [pKi]
5-hydroxytryptamine receptor 1B 21 Target ID: CHEMBL5717 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11522469	Inverse Agonist 80	7.55 null [pKi]
Serotonin 1d (5-HT1d) receptor 52 Target ID: CHEMBL1983 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11522469	Inverse Agonist 80	8.43 null [pKi]

PubMed

Title	Date	PubMed
Alniditan, a new 5-hydroxytryptamine1D agonist and migraine-abortive agent: ligand-binding properties of human 5-hydroxytryptamine1D alpha, human 5-hydroxytryptamine1D beta, and calf 5-hydroxytryptamine1D receptors investigated with [3H]5-hydroxytryptamine and [3H]alniditan.	1996 Dec	8967979
5-HT1A receptor activates Na+/H+ exchange in CHO-K1 cells through Gialpha2 and Gialpha3.	1997 Mar 21	9065439
Agonistic properties of alniditan, sumatriptan and dihydroergotamine on human 5-HT1B and 5-HT1D receptors expressed in various mammalian cell lines.	1998 Apr	9605573

Patents

Sample Use Guides

In Vivo Use Guide

Ocaperidone was studied at various time intervals after s.c. (10 ml/kg for rats and 0.5 ml/kg for dogs), oral (10 ml/kg for mice and rats and 0.5 ml/kg for dogs) or i.v. administration (10 ml/kg for mice, 2 ml/kg for rats and 0.5 ml/kg for dogs).

Route of Administration: Other

In Vitro Use Guide

Ocaperidone is an effective antipsychotic agent, acting as a potent 5-HT2 and dopamine D2 antagonist, and a 5-HT1A agonist, with Kis of 0.14 nM, 0.46 nM, 0.75 nM, 1.6 nM and 5.4 nM for 5-HT2, a1-adrenergic receptor, dopamine D2, histamine H1 and a2-adrenergic receptor, respectively, and a pEC50 and pKi of 7.60 and 8.08 for h5-HT1A.

Name

Type

Language

OCAPERIDONE

Official Name

English

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

Systematic Name

English

3-[2-[4-(6-Fluoro-1,2-benzisoxazol-3-yl)piperidino]ethyl]-2,9-dimethyl-4H-pyrido[1,2-a]pyrimidin-4-one

Systematic Name

English

OCAPERIDONE [USAN]

Common Name

English

R-79598

Code

English

ocaperidone [INN]

Common Name

English

R 79598

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C29710