azithromycin   Click here for help

GtoPdb Ligand ID: 6510

Approved drug PDB Ligand Antimalarial Ligand
azithromycin is an approved drug (FDA & UK (1991))
Compound class: Synthetic organic
Comment: Azithromycin is a macrolide antibiotic with broad-spectrum activity against Gram-positive and atypical bacteria. The compound also has antimalarial activity.
Azithromycin is one of the watch group antibacterials in the the World Health Organisation's List of Essential Medicines (link provided in the Classification table below).

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 14
Hydrogen bond donors 5
Rotatable bonds 7
Topological polar surface area 180.08
Molecular weight 748.51
XLogP 1.89
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES CCC1OC(=O)C(C)C(OC2OC(C)C(C(C2)(C)OC)O)C(C)C(OC2OC(C)CC(C2O)N(C)C)C(CC(CN(C(C(C1(C)O)O)C)C)C)(C)O
Isomeric SMILES CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@@H]2O[C@@H](C)[C@@H]([C@](C2)(C)OC)O)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@](C[C@H](CN([C@@H]([C@H]([C@]1(C)O)O)C)C)C)(C)O
InChI InChI=1S/C38H72N2O12/c1-15-27-38(10,46)31(42)24(6)40(13)19-20(2)17-36(8,45)33(52-35-29(41)26(39(11)12)16-21(3)48-35)22(4)30(23(5)34(44)50-27)51-28-18-37(9,47-14)32(43)25(7)49-28/h20-33,35,41-43,45-46H,15-19H2,1-14H3/t20-,21-,22+,23-,24-,25+,26+,27-,28+,29-,30+,31-,32+,33-,35+,36-,37-,38-/m1/s1
InChI Key MQTOSJVFKKJCRP-BICOPXKESA-N
No information available.
Summary of Clinical Use Click here for help
Azithromycin is approved for use in both the US and the UK. It is also available in other countries under various trade names, click here to link to Drugs.com's list of internationally marketed azithromycin drugs.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Although the mechanism of action in the Plasmodium parasite has not been fully elucidated, it is thought that azithromycin inhibits the production of proteins encoded by the apicoplast genome, leading to a subsequent loss of apicoplast function and a possible explanation for the delayed antimalarial effect [2].
External links Click here for help