PIRENPERONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C23H24FN3O2
Molecular Weight	393.454
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=C(CCN2CCC(CC2)C(=O)C3=CC=C(F)C=C3)C(=O)N4C=CC=CC4=N1

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	393.454
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6202264 | https://www.ncbi.nlm.nih.gov/pubmed/3081929

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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Serotonin 2b (5-HT2b) receptor 60 Target ID: CHEMBL1833 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8632342	Antagonist 2778	61.0 nM [Ki]
Serotonin 2a (5-HT2a) receptor 231 Target ID: CHEMBL224 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8632342	Antagonist 2778	1.08 nM [Ki]
Serotonin 2c (5-HT2c) receptor 124 Target ID: CHEMBL225 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8632342	Antagonist 2778	77.0 nM [Ki]
Serotonin 7 (5-HT7) receptor 31 Target ID: CHEMBL3155 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9298538	Antagonist 2778	8.19 null [pKi]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Central antiserotonergic and antidopaminergic action of pirenperone, a putative 5-HT2 receptor antagonist.	1985 Mar-Apr	4048012
Cocaine-induced convulsions: pharmacological antagonism at serotonergic, muscarinic and sigma receptors.	1997 Feb	9085399
Cloning, expression and pharmacology of a truncated splice variant of the human 5-HT7 receptor (h5-HT7b).	1997 Sep	9298538
The role of serotonin(2) receptors in mediating cocaine-induced convulsions.	2000 Apr	10764922

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 Dec 15 16:25:35 UTC 2023` Edited by `admin` on `Fri Dec 15 16:25:35 UTC 2023`
Record UNII	Y9FMC4513X
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PIRENPERONE

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