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
1. Baumann L, Gerstner A, Zong X, Biel M, Wahl-Schott C. (2004)
Functional characterization of the L-type Ca2+ channel Cav1.4alpha1 from mouse retina.
Invest Ophthalmol Vis Sci, 45 (2): 708-13. [PMID:14744918]
2. Grissmer S, Nguyen AN, Aiyar J, Hanson DC, Mather RJ, Gutman GA, Karmilowicz MJ, Auperin DD, Chandy KG. (1994)
Pharmacological characterization of five cloned voltage-gated K+ channels, types Kv1.1, 1.2, 1.3, 1.5, and 3.1, stably expressed in mammalian cell lines.
Mol Pharmacol, 45 (6): 1227-34. [PMID:7517498]
3. Gunthorpe MJ, Lummis SC. (1999)
Diltiazem causes open channel block of recombinant 5-HT3 receptors.
J Physiol (Lond.), 519 Pt 3: 713-22. [PMID:10457085]
4. Kalman K, Nguyen A, Tseng-Crank J, Dukes ID, Chandy G, Hustad CM, Copeland NG, Jenkins NA, Mohrenweiser H, Brandriff B et al.. (1998)
Genomic organization, chromosomal localization, tissue distribution, and biophysical characterization of a novel mammalian Shaker-related voltage-gated potassium channel, Kv1.7.
J Biol Chem, 273 (10): 5851-7. [PMID:9488722]
5. Kanaya S, Katzung BG. (1984)
Effects of diltiazem on transmembrane potential and current of right ventricular papillary muscle of ferrets.
J Pharmacol Exp Ther, 228 (1): 245-51. [PMID:6694106]
6. Lee BH, Choi SH, Pyo MK, Shin TJ, Hwang SH, Kim BR, Lee JH, Rhim H, Kim HC, Nah SY. (2009)
A role for the Val291 residue within the transmembrane domain 2 in diltiazem- and TMB-8 [3,4,5-trimethoxybenzoic acid 8-(diethylamino)octyl ester]-mediated 5-hydroxytryptamine type 3A receptor regulations.
Biol Pharm Bull, 32 (5): 861-7. [PMID:19420755]
7. Tarabova B, Lacinova L, Engel J. (2007)
Effects of phenylalkylamines and benzothiazepines on Ca(v)1.3-mediated Ca2+ currents in neonatal mouse inner hair cells.
Eur J Pharmacol, 573 (1-3): 39-48. [PMID:17651721]
8. Thompson AJ, Duke RK, Lummis SC. (2011)
Binding sites for bilobalide, diltiazem, ginkgolide, and picrotoxinin at the 5-HT3 receptor.
Mol Pharmacol, 80 (1): 183-90. [PMID:21505038]
9. Walsh KB, Bryant SH, Schwartz A. (1986)
Effect of calcium antagonist drugs on calcium currents in mammalian skeletal muscle fibers.
J Pharmacol Exp Ther, 236 (2): 403-7. [PMID:2418195]