Structure
Isosorbide dinitrite Chemical Structure – C6H8N2O8
Structure-Activity Relationship (SAR) of Isosorbide Dinitrate
Nitrate Groups:
Isosorbide dinitrate contains two nitrate ester groups.
These groups are key for its activity as they are reduced in the body to form nitric oxide (NO), a potent vasodilator.
The presence of two nitrate groups increases the potency and duration of action compared to nitroglycerin, which has three.
Isosorbide Ring:
The isosorbide moiety (a bicyclic structure derived from sorbitol) is essential for the stability of the molecule and influences its pharmacokinetic properties.
The ring structure allows for a sustained release of NO as the nitrate groups are gradually metabolized.
Stereochemistry:
The specific spatial arrangement of the isosorbide molecule plays a role in its biological activity.
The stereochemistry affects how the drug interacts with enzymes that convert it to NO.
Synthesis of Isosorbide Dinitrate
The synthesis of isosorbide dinitrate typically involves the nitration of isosorbide.
The reaction can be simplified as follows:
Nitration Reaction:
C6H10O4+2HNO3→C6H8O8(NO2)2+2H2O
In this reaction, isosorbide (C6H10O4) is treated with nitric acid (HNO3) to yield isosorbide dinitrate (C6H8O8(NO2)2) along with water.
This synthesis is a nitration reaction where nitric acid acts as a nitrating agent, introducing nitrate ester groups into the isosorbide molecule.
The reaction typically requires careful control of conditions, such as temperature and acid concentration, to ensure the correct degree of nitration and to maintain the stability of the compound.
Mode of action
Nitric oxide is produced by the conversion of isosorbide dinitrate (NO), which raises the level of cyclic GMP in smooth muscle and other tissues. . It causes blood arteries to dilate (vasodilator), which lowers blood pressure.
Uses
This In the treatment of angina in coronary artery disease, isosorbide dinitrate is a vasodilator.