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Details

Stereochemistry ACHIRAL
Molecular Formula C13H16N2O2
Molecular Weight 232.2783
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIRMAGREL

SMILES

OC(=O)CCCCCC1=CC=CC2=CN=CN12

InChI

InChIKey=LIFOFTJHFFTNRV-UHFFFAOYSA-N
InChI=1S/C13H16N2O2/c16-13(17)8-3-1-2-5-11-6-4-7-12-9-14-10-15(11)12/h4,6-7,9-10H,1-3,5,8H2,(H,16,17)

HIDE SMILES / InChI

Molecular Formula C13H16N2O2
Molecular Weight 232.2783
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Pirmagrel is the selective thromboxane synthetase inhibitor. The compound was well tolerated by all subjects without evidence of any adverse reactions. Serum thromboxane B2 levels (the stable metabolic product of thromboxane A2) were significantly reduced after administration of the compound, with the maximal effect of a 99 per cent reduction occurring at 0.5 and 1 hour after administration. Bleeding times showed a slight increase 2 hours after administration of the compound. Pirmagrel was able to completely prevent the increase in serum thromboxane B2 following allergen challenge in asthmatic patients; while it caused a very small reduction in the early response to allergen, there was no effect on the late response or on airway hyperresponsiveness. Pirmagrel was developed for the treatment of ischemic heart disorders and thrombosis. However, this development was discontinued.

Approval Year

PubMed

PubMed

TitleDatePubMed
Antioxidants condition pleiotropic vascular responses to exogenous H(2)O(2): role of modulation of vascular TP receptors and the heme oxygenase system.
2013-02-10
Modulation of prostacyclin and thromboxane secretion by cytotrophoblasts from normal and pre-eclamptic human pregnancies.
2002-10-04
Critical role of endothelial nitric oxide synthase and cyclooxygenase in response of rabbit basilar artery to serotonin.
2002-09
Effects of ethanol and arachidonic acid pathway inhibitors on the effectiveness of gastric mucosa cytoprotection.
2001
Effects of hypoxia on regulation of prostanoid production in decidual endothelial cells in normal and preeclamptic pregnancy.
2000-04-29
Thromboxane A2 contributes to the enhanced tubuloglomerular feedback activity in young SHR.
1999-05
Endothelial dysfunction in the aorta of transgenic rats harboring the mouse Ren-2 gene.
1999
The influence of certain arachidonic acid pathway inhibitors on central nervous system catecholamine level in rats administered with ethanol.
1998
Autacoids mediate coronary vasoconstriction induced by nitric oxide synthesis inhibition.
1997-11
Analysis of eicosanoid mediation of the renal functional effects of hyperchloremia.
1997-07
Endothelial vasoconstrictor prostanoids modulate contractions to acetylcholine and ANG II in Ren-2 rats.
1997-01
Peroxide-cyclooxygenase interactions in postasphyxial changes in retinal and choroidal hemodynamics.
1995-06
Increased thromboxane-mediated contractions of retinal vessels of newborn pigs to peroxides.
1995-02
Long-term renal preservation and prevention of acute tubular necrosis by inhibition of arachidonate metabolism.
1995
1986: Pharmacological, hematological, and physiological effects of a new thromboxane synthetase inhibitor (CGS-13080) during cardiopulmonary bypass in dogs. Updated in 1994.
1994-03
Differential antagonism of airway contractile responses to prostaglandin (PG)D2 and 9 alpha, 11 beta-PGF2 by atropine, SK&F 88046 and SQ 29,548 in the guinea pig.
1994-01
Chronic thromboxane synthase inhibition with CGS 12970 in human cyclosporine nephrotoxicity.
1993-12
Endothelial dysfunction augments myogenic arteriolar constriction in hypertension.
1993-12
Suppression of S-antigen-induced experimental autoimmune uveoretinitis in Lewis rats by oral administration with CGS-13080, a thromboxane synthetase inhibitor.
1993-11
Long-term renal preservation and prevention of acute tubular necrosis by inhibition of arachidonate metabolism.
1993-08
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:57:42 GMT 2025
Edited
by admin
on Mon Mar 31 17:57:42 GMT 2025
Record UNII
9J5H2VA91V
Record Status Validated (UNII)
Record Version
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Name Type Language
PIRMAGREL
INN   MART.   USAN  
INN   USAN  
Official Name English
CGS 13080
Preferred Name English
pirmagrel [INN]
Common Name English
PIRMAGREL [MART.]
Common Name English
PIRMAGREL [USAN]
Common Name English
Imidazo[1,5-a]pyridine-5-hexanoic acid
Systematic Name English
CGS-13080
Code English
Classification Tree Code System Code
NCI_THESAURUS C1327
Created by admin on Mon Mar 31 17:57:42 GMT 2025 , Edited by admin on Mon Mar 31 17:57:42 GMT 2025
NCI_THESAURUS C574
Created by admin on Mon Mar 31 17:57:42 GMT 2025 , Edited by admin on Mon Mar 31 17:57:42 GMT 2025
Code System Code Type Description
FDA UNII
9J5H2VA91V
Created by admin on Mon Mar 31 17:57:42 GMT 2025 , Edited by admin on Mon Mar 31 17:57:42 GMT 2025
PRIMARY
EVMPD
SUB09924MIG
Created by admin on Mon Mar 31 17:57:42 GMT 2025 , Edited by admin on Mon Mar 31 17:57:42 GMT 2025
PRIMARY
EPA CompTox
DTXSID80234982
Created by admin on Mon Mar 31 17:57:42 GMT 2025 , Edited by admin on Mon Mar 31 17:57:42 GMT 2025
PRIMARY
ChEMBL
CHEMBL2104615
Created by admin on Mon Mar 31 17:57:42 GMT 2025 , Edited by admin on Mon Mar 31 17:57:42 GMT 2025
PRIMARY
PUBCHEM
55390
Created by admin on Mon Mar 31 17:57:42 GMT 2025 , Edited by admin on Mon Mar 31 17:57:42 GMT 2025
PRIMARY
NCI_THESAURUS
C96933
Created by admin on Mon Mar 31 17:57:42 GMT 2025 , Edited by admin on Mon Mar 31 17:57:42 GMT 2025
PRIMARY
USAN
W-46
Created by admin on Mon Mar 31 17:57:42 GMT 2025 , Edited by admin on Mon Mar 31 17:57:42 GMT 2025
PRIMARY
CAS
85691-74-3
Created by admin on Mon Mar 31 17:57:42 GMT 2025 , Edited by admin on Mon Mar 31 17:57:42 GMT 2025
PRIMARY
INN
5691
Created by admin on Mon Mar 31 17:57:42 GMT 2025 , Edited by admin on Mon Mar 31 17:57:42 GMT 2025
PRIMARY
SMS_ID
100000081673
Created by admin on Mon Mar 31 17:57:42 GMT 2025 , Edited by admin on Mon Mar 31 17:57:42 GMT 2025
PRIMARY
Related Record Type Details
ACTIVE MOIETY