U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C18H17N3O2
Molecular Weight 307.3465
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIRODOMAST

SMILES

OC1=C(N2CCCC2)C(=O)N(C3=CC=CC=C3)C4=C1C=CC=N4

InChI

InChIKey=ULGABHCZIJXUFO-UHFFFAOYSA-N
InChI=1S/C18H17N3O2/c22-16-14-9-6-10-19-17(14)21(13-7-2-1-3-8-13)18(23)15(16)20-11-4-5-12-20/h1-3,6-10,22H,4-5,11-12H2

HIDE SMILES / InChI
Pirodomast is Thromboxane A (TXA2) synthetase inhibitor. Pirodomast can inhibit leukotriene (LT) D4, C4, E4 formation and Thromboxane B2 (TXB2) activities. It was weak or ineffective as an antagonist of histamine, methacholine, serotonin, LTC4 or platelet activating factor induced bronchospasms in guinea pigs. Also, pirodomast was not a bronchodilator or calcium influx blocker and had only weak relaxant activity on guinea pig trachea in vitro. Pirodomast is, therefore, a potential antiallergic agent that inhibits leukotriene (LT) release. Pirodomast inhibited tryptase proteolytic activity in-vitro. In experimental studies in vivo, pirodomast blocked antigen-induced immediate and late asthmatic responses in allergic sheep. Pirodomast inhibited antigen-induced airway hyperresponsiveness to both histamine and carbachol in allergic sheep. Pirodomast was being investigated for use in asthma and allergic rhinitis.

Approval Year

PubMed

PubMed

TitleDatePubMed
Antiallergy activity of Sch 37224, a new inhibitor of leukotriene formation.
1988 Dec
A leukotriene and thromboxane inhibitor (Sch 37224) blocks antigen-induced immediate and late responses and airway hyperresponsiveness in allergic sheep.
1988 Dec
Anaphylactic challenge causes eosinophil accumulation in bronchoalveolar lavage fluid of guinea pigs. Modulation by betamethasone, phenidone, indomethacin, WEB 2086, and a novel antiallergy agent, SCH 37224.
1990 Sep
Effect of SCH 37224 on anti-IgE-induced formation of sulfidopeptide leukotrienes in human lung parenchyma.
1992 Aug 14
Effect of leukotriene inhibitor on cochlear blood flow in salicylate ototoxicity.
1995 Mar
Effect of leukotriene inhibitor on otoacoustic emissions in salicylate ototoxicity.
1996 Sep
Sch 37224, an experimental antiallergy compound, inhibits the neuropeptide component of hyperventilation- and nicotine-induced bronchoconstriction in guinea pigs.
1997 Jan
Tryptase-induced airway microvascular leakage in guinea pigs: involvement of tachykinins and leukotrienes.
2001 May 11
Effect of inhibitors of leukotriene and/or platelet activating factor on killed H. influenzae induced experimental otitis media with effusion.
2004 Jan
Patents
Name Type Language
PIRODOMAST
INN  
INN  
Official Name English
4-HYDROXY-1-PHENYL-3-(1-PYRROLIDINYL)-1,8-NAPHTHYRIDIN-2-(1H)-ONE
Common Name English
pirodomast [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29712
Created by admin on Sat Dec 16 17:52:59 GMT 2023 , Edited by admin on Sat Dec 16 17:52:59 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C82230
Created by admin on Sat Dec 16 17:52:59 GMT 2023 , Edited by admin on Sat Dec 16 17:52:59 GMT 2023
PRIMARY
INN
6669
Created by admin on Sat Dec 16 17:52:59 GMT 2023 , Edited by admin on Sat Dec 16 17:52:59 GMT 2023
PRIMARY
PUBCHEM
54680204
Created by admin on Sat Dec 16 17:52:59 GMT 2023 , Edited by admin on Sat Dec 16 17:52:59 GMT 2023
PRIMARY
EPA CompTox
DTXSID20148498
Created by admin on Sat Dec 16 17:52:59 GMT 2023 , Edited by admin on Sat Dec 16 17:52:59 GMT 2023
PRIMARY
ChEMBL
CHEMBL2105217
Created by admin on Sat Dec 16 17:52:59 GMT 2023 , Edited by admin on Sat Dec 16 17:52:59 GMT 2023
PRIMARY
SMS_ID
100000081695
Created by admin on Sat Dec 16 17:52:59 GMT 2023 , Edited by admin on Sat Dec 16 17:52:59 GMT 2023
PRIMARY
FDA UNII
1S2EOV9V3Z
Created by admin on Sat Dec 16 17:52:59 GMT 2023 , Edited by admin on Sat Dec 16 17:52:59 GMT 2023
PRIMARY
CAS
108310-20-9
Created by admin on Sat Dec 16 17:52:59 GMT 2023 , Edited by admin on Sat Dec 16 17:52:59 GMT 2023
PRIMARY
EVMPD
SUB09929MIG
Created by admin on Sat Dec 16 17:52:59 GMT 2023 , Edited by admin on Sat Dec 16 17:52:59 GMT 2023
PRIMARY