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Details

Stereochemistry ACHIRAL
Molecular Formula C24H25FN4O2
Molecular Weight 420.4802
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OCAPERIDONE

SMILES

Cc1cccn2c1nc(C)c(CCN3CCC(CC3)c4c5ccc(cc5on4)F)c2=O

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

HIDE SMILES / InChI

Molecular Formula C24H25FN4O2
Molecular Weight 420.4802
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
9.52 null [pKi]
7.55 null [pKi]
8.43 null [pKi]
PubMed

PubMed

TitleDatePubMed
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
5-HT1A receptor activates Na+/H+ exchange in CHO-K1 cells through Gialpha2 and Gialpha3.
1997 Mar 21
Agonistic properties of alniditan, sumatriptan and dihydroergotamine on human 5-HT1B and 5-HT1D receptors expressed in various mammalian cell lines.
1998 Apr
Patents

Sample Use Guides

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
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.
Substance Class Chemical
Created
by admin
on Fri Jun 25 22:21:26 UTC 2021
Edited
by admin
on Fri Jun 25 22:21:26 UTC 2021
Record UNII
26HUS7139V
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OCAPERIDONE
INN   USAN  
USAN   INN  
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
Created by admin on Fri Jun 25 22:21:26 UTC 2021 , Edited by admin on Fri Jun 25 22:21:26 UTC 2021
Code System Code Type Description
ChEMBL
CHEMBL2104619
Created by admin on Fri Jun 25 22:21:26 UTC 2021 , Edited by admin on Fri Jun 25 22:21:26 UTC 2021
PRIMARY
EVMPD
SUB09395MIG
Created by admin on Fri Jun 25 22:21:26 UTC 2021 , Edited by admin on Fri Jun 25 22:21:26 UTC 2021
PRIMARY
FDA UNII
26HUS7139V
Created by admin on Fri Jun 25 22:21:26 UTC 2021 , Edited by admin on Fri Jun 25 22:21:26 UTC 2021
PRIMARY
WIKIPEDIA
Ocaperidone
Created by admin on Fri Jun 25 22:21:26 UTC 2021 , Edited by admin on Fri Jun 25 22:21:26 UTC 2021
PRIMARY
INN
6679
Created by admin on Fri Jun 25 22:21:26 UTC 2021 , Edited by admin on Fri Jun 25 22:21:26 UTC 2021
PRIMARY
PUBCHEM
71351
Created by admin on Fri Jun 25 22:21:26 UTC 2021 , Edited by admin on Fri Jun 25 22:21:26 UTC 2021
PRIMARY
CAS
129029-23-8
Created by admin on Fri Jun 25 22:21:26 UTC 2021 , Edited by admin on Fri Jun 25 22:21:26 UTC 2021
PRIMARY
DRUG BANK
DB06229
Created by admin on Fri Jun 25 22:21:26 UTC 2021 , Edited by admin on Fri Jun 25 22:21:26 UTC 2021
PRIMARY
EPA CompTox
129029-23-8
Created by admin on Fri Jun 25 22:21:26 UTC 2021 , Edited by admin on Fri Jun 25 22:21:26 UTC 2021
PRIMARY
NCI_THESAURUS
C76441
Created by admin on Fri Jun 25 22:21:26 UTC 2021 , Edited by admin on Fri Jun 25 22:21:26 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
TARGET -> AGONIST
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY