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Details

Stereochemistry ACHIRAL
Molecular Formula C23H24FN3O2
Molecular Weight 393.4548
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIRENPERONE

SMILES

Cc1c(CCN2CCC(CC2)C(=O)c3ccc(cc3)F)c(=O)n4ccccc4n1

InChI

InChIKey=HXCNRYXBZNHDNE-UHFFFAOYSA-N
InChI=1S/C23H24FN3O2/c1-16-20(23(29)27-12-3-2-4-21(27)25-16)11-15-26-13-9-18(10-14-26)22(28)17-5-7-19(24)8-6-17/h2-8,12,18H,9-11,13-15H2,1H3

HIDE SMILES / InChI

Molecular Formula C23H24FN3O2
Molecular Weight 393.4548
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Pirenperone, a quinazoline derivative, is a selective antagonist at serotonin receptor 2A binding sites. The liposoluble compound pirenperone has been studied in a variety of behavioral tests including the sensitive d-lysergic acid diethylamide (LSD) cue discrimination assay, in which it served as a potent LSD-antagonist. Pirenperone also proved to be an effective antagonist of serotonin-mediated behavioral responses including the head twitch response thought to be mediated by serotonin receptors.

Originator

Curator's Comment:: # Janssen Pharmaceutica N.V.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Central antiserotonergic and antidopaminergic action of pirenperone, a putative 5-HT2 receptor antagonist.
1985 Mar-Apr
Cocaine-induced convulsions: pharmacological antagonism at serotonergic, muscarinic and sigma receptors.
1997 Feb
Cloning, expression and pharmacology of a truncated splice variant of the human 5-HT7 receptor (h5-HT7b).
1997 Sep
The role of serotonin(2) receptors in mediating cocaine-induced convulsions.
2000 Apr
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
The steric chemical information was used to predict the activity of serotonergic compounds that had never been analyzed at serotonin 3 (5-HT3) receptor binding sites. Two serotonergic drugs that meet all steric criteria were found to be active at the 5-HT3 receptor binding site (i.e., pizotifen, Ki = 42 +/- 10 nM, and clozapine, Ki = 52 +/- 8 nM). By contrast, two serotonergic agents that do not meet the criteria were found to be inactive at the 5-HT3 receptor binding site (i.e., ipsapirone and pirenperone, Ki values greater than 1000 nM).
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:53:40 UTC 2021
Edited
by admin
on Fri Jun 25 21:53:40 UTC 2021
Record UNII
Y9FMC4513X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PIRENPERONE
USAN   INN  
Official Name English
R-47,465
Code English
PIRENPERONE [INN]
Common Name English
4H-PYRIDO(1,2-A)PYRIMIDIN-4-ONE, 3-(2-(4-(4-FLUOROBENZOYL)-1-PIPERIDINYL)ETHYL)-2-METHYL-
Systematic Name English
3-(2-(4-(4-FLUOROBENZOYL)PIPERIDIN-1-YL)ETHYL)-2-METHYL-4H-PYRIDO(1,2-A)PYRIMIDIN-4-ONE
Systematic Name English
R-47465
Code English
NSC-760095
Code English
PIRENPERONE [USAN]
Common Name English
PIRENPERONE [MART.]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C28197
Created by admin on Fri Jun 25 21:53:40 UTC 2021 , Edited by admin on Fri Jun 25 21:53:40 UTC 2021
Code System Code Type Description
EPA CompTox
75444-65-4
Created by admin on Fri Jun 25 21:53:40 UTC 2021 , Edited by admin on Fri Jun 25 21:53:40 UTC 2021
PRIMARY
MESH
C034177
Created by admin on Fri Jun 25 21:53:40 UTC 2021 , Edited by admin on Fri Jun 25 21:53:40 UTC 2021
PRIMARY
FDA UNII
Y9FMC4513X
Created by admin on Fri Jun 25 21:53:40 UTC 2021 , Edited by admin on Fri Jun 25 21:53:40 UTC 2021
PRIMARY
INN
5065
Created by admin on Fri Jun 25 21:53:40 UTC 2021 , Edited by admin on Fri Jun 25 21:53:40 UTC 2021
PRIMARY
ChEMBL
CHEMBL18331
Created by admin on Fri Jun 25 21:53:40 UTC 2021 , Edited by admin on Fri Jun 25 21:53:40 UTC 2021
PRIMARY
ECHA (EC/EINECS)
278-213-5
Created by admin on Fri Jun 25 21:53:40 UTC 2021 , Edited by admin on Fri Jun 25 21:53:40 UTC 2021
PRIMARY
EVMPD
SUB09903MIG
Created by admin on Fri Jun 25 21:53:40 UTC 2021 , Edited by admin on Fri Jun 25 21:53:40 UTC 2021
PRIMARY
PUBCHEM
4847
Created by admin on Fri Jun 25 21:53:40 UTC 2021 , Edited by admin on Fri Jun 25 21:53:40 UTC 2021
PRIMARY
CAS
75444-65-4
Created by admin on Fri Jun 25 21:53:40 UTC 2021 , Edited by admin on Fri Jun 25 21:53:40 UTC 2021
PRIMARY
NCI_THESAURUS
C66417
Created by admin on Fri Jun 25 21:53:40 UTC 2021 , Edited by admin on Fri Jun 25 21:53:40 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY