amiodarone   Click here for help

GtoPdb Ligand ID: 2566

Synonyms: amiodarone hydrochloride | Cordarone®
Approved drug PDB Ligand
amiodarone is an approved drug (FDA (1985))
Compound class: Synthetic organic
Comment: Amiodarone is a class III antiarrhythmic drug and acts as a positive inotropic agent. The prescription drug contains amiodarone hydrochloride (PubChem CID 441325).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 0
Rotatable bonds 11
Topological polar surface area 42.68
Molecular weight 645.02
XLogP 7.91
No. Lipinski's rules broken 2
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Canonical SMILES CCCCc1oc2c(c1C(=O)c1cc(I)c(c(c1)I)OCCN(CC)CC)cccc2
Isomeric SMILES CCCCc1oc2c(c1C(=O)c1cc(I)c(c(c1)I)OCCN(CC)CC)cccc2
InChI InChI=1S/C25H29I2NO3/c1-4-7-11-22-23(18-10-8-9-12-21(18)31-22)24(29)17-15-19(26)25(20(27)16-17)30-14-13-28(5-2)6-3/h8-10,12,15-16H,4-7,11,13-14H2,1-3H3
1. Bardien-Kruger S, Wulff H, Arieff Z, Brink P, Chandy KG, Corfield V. (2002)
Characterisation of the human voltage-gated potassium channel gene, KCNA7, a candidate gene for inherited cardiac disorders, and its exclusion as cause of progressive familial heart block I (PFHBI).
Eur J Hum Genet, 10 (1): 36-43. [PMID:11896454]
2. Sheldon RS, Hill RJ, Cannon NJ, Duff HJ. (1989)
Amiodarone: biochemical evidence for binding to a receptor for class I drugs associated with the rat cardiac sodium channel.
Circ Res, 65 (2): 477-82. [PMID:2546697]
3. Stahl E, Ellis J. (2010)
Novel allosteric effects of amiodarone at the muscarinic M5 receptor.
J Pharmacol Exp Ther, 334 (1): 214-22. [PMID:20348203]