isosorbide mononitrate   Click here for help

GtoPdb Ligand ID: 7052

Synonyms: AHR-4698 | BM-22-145 | Imdur® | IS-5-MN | ISMN | Monosorb®
Approved drug
isosorbide mononitrate is an approved drug (FDA (1991))
Compound class: Synthetic organic
Comment: Isosorbide mononitrate is termed a nitrate drug and acts as a vasodilator. It is similar to nitroglycerin, but is slower to act.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 2
Topological polar surface area 91.06
Molecular weight 191.04
XLogP -0.91
No. Lipinski's rules broken 0
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Canonical SMILES [O-][N+](=O)OC1COC2C1OCC2O
Isomeric SMILES [O-][N+](=O)O[C@@H]1CO[C@H]2[C@@H]1OC[C@@H]2O
InChI InChI=1S/C6H9NO6/c8-3-1-11-6-4(13-7(9)10)2-12-5(3)6/h3-6,8H,1-2H2/t3-,4+,5+,6+/m0/s1
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Summary of Clinical Use Click here for help
Isosorbide mononitrate is used to prevent angina chest pains.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Nitrates reduce the workload of the heart by causing venous and arterial dilation. The pathway includes production of nitric oxide (NO), activation of guanylate cyclase, increased synthesis of cGMP, activation of kinase-dependent phosphorylation in the smooth muscle cells and eventual dephosphorylation of myosin light chains in the smooth muscle fibers. This sequence of events culminates in the release of calcium ions, which causes smooth muscle relaxation and vasodilation. See the DrugBank link for further details.