Details
Stereochemistry | RACEMIC |
Molecular Formula | C26H33NO6 |
Molecular Weight | 455.5433 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=C(OCCN2CCCCC2)C(C(O)CCC3=CC=C(O)C=C3)=C(OC)C4=C1OC=C4
InChI
InChIKey=LIAPJIQUUKLLDZ-UHFFFAOYSA-N
InChI=1S/C26H33NO6/c1-30-23-20-12-16-32-24(20)26(31-2)25(33-17-15-27-13-4-3-5-14-27)22(23)21(29)11-8-18-6-9-19(28)10-7-18/h6-7,9-10,12,16,21,28-29H,3-5,8,11,13-15,17H2,1-2H3
Piprofurol is a benzofuran chalcon derivative. It is a calcium channel blocker. Piprofurol inhibited in a concentration-dependent manner the calcium-induced contractions in isolated potassium depolarized preparations of rat aorta and relaxed the K+-induced contraction of the dog coronary artery and the rabbit basilar artery. Piprofurol also inhibited noradrenaline-induced vascular smooth muscle contractions but the antagonism was clearly noncompetitive and the contractions induced were altered by concentrations two orders of magnitude higher than the concentration inhibiting calcium-induced contractions. Piprofurol exerts a negative inotropic effect on guinea-pig papillary muscle. These effects suggested a potentially anti-ischemic activity. This is confirmed in anaesthetized dogs, where piprofurol reduced the epicardial ST-segment elevation following coronary artery occlusion, and in isolated heart preparations, where it decreased the leakage of LDH during periods of anoxia and reoxygenation. Piprofurol is a coronary vasodilator and antihypertensive agent.
Approval Year
PubMed
Title | Date | PubMed |
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[Significance of pharmacodynamics tests in the study of sinus node function]. | 1976 Jan |
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[Effect of a depressant drug on the recovery time of the sinus. Attempt of application to the diagnosis of sinus dysfunctions]. | 1977 Sep |
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Calcium blocking properties of piprofurol. | 1985 Apr |
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NCI_THESAURUS |
C333
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3600
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38596
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255-035-6
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SUB09888MIG
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C66409
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C013201
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40680-87-3
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ACTIVE MOIETY