diltiazem   Click here for help

GtoPdb Ligand ID: 2298

Synonyms: (+)-cis-diltiazem | Cardizem® | CRD-401 | D-(cis)-diltiazem | Dilacor-XR® | RG-83606
Approved drug PDB Ligand
diltiazem is an approved drug (FDA (1982))
Compound class: Synthetic organic
Comment: Diltiazem has vasodilating actions.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 0
Rotatable bonds 7
Topological polar surface area 84.38
Molecular weight 414.16
XLogP 2.84
No. Lipinski's rules broken 0
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Canonical SMILES COc1ccc(cc1)C1Sc2ccccc2N(C(=O)C1OC(=O)C)CCN(C)C
Isomeric SMILES COc1ccc(cc1)[C@@H]1Sc2ccccc2N(C(=O)[C@@H]1OC(=O)C)CCN(C)C
InChI InChI=1S/C22H26N2O4S/c1-15(25)28-20-21(16-9-11-17(27-4)12-10-16)29-19-8-6-5-7-18(19)24(22(20)26)14-13-23(2)3/h5-12,20-21H,13-14H2,1-4H3/t20-,21+/m1/s1
No information available.
Summary of Clinical Use Click here for help
Used in the treatment of hypertension, chronic stable angina pectoris, and Prinzmetal's variant angina, either alone or in combination with an ACE inhibitor.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Diltiazem appears to block voltage-dependent L-type calcium channels, but the exact machanism remains unclear. However, the drug-induced effect is a decrease in intracellular calcium in myocardial and vascular smooth muscle cells which causes inhibition of contraction in myocardial smooth muscle cells, and dilation of the coronary and systemic arteries. The net result is improved blood flow and oxygen delivery to myocardial tissues and improved function.