GtoPdb is requesting financial support from commercial users. Please see our sustainability page for more information.

isosorbide dinitrate   Click here for help

GtoPdb Ligand ID: 7051

Synonyms: Dilatrate-Sr® | ISDN | Isordil®
Approved drug
isosorbide dinitrate is an approved drug (FDA (no history prior to 1968))
Compound class: Synthetic organic
Comment: Isosorbide dinitrate acts as a vasodilator. It is similar to nitroglycerin, but is slower to act.
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: isosorbide dinitrate

isosorbide dinitrate is commercially available from our sponsors

2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
Hydrogen bond acceptors 2
Hydrogen bond donors 0
Rotatable bonds 4
Topological polar surface area 123.2
Molecular weight 236.03
XLogP 0.04
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

✖
Canonical SMILES [O-][N+](=O)OC1COC2C1OCC2O[N+](=O)[O-]
Isomeric SMILES [O-][N+](=O)O[C@@H]1CO[C@H]2[C@@H]1OC[C@@H]2O[N+](=O)[O-]
InChI InChI=1S/C6H8N2O8/c9-7(10)15-3-1-13-6-4(16-8(11)12)2-14-5(3)6/h3-6H,1-2H2/t3-,4+,5-,6-/m1/s1
InChI Key MOYKHGMNXAOIAT-JGWLITMVSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
Used to treat angina.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Isosorbide dinitrate is converted to nitric oxide (NO). This activates soluble guanylyl cyclase which in turn increases cGMP synthesis, leading to downstream release of calcium ions and finally relaxation of the smooth muscle cells and vasodilation.