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.
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2D Structure
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Physico-chemical Properties
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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
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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
Guide to Malaria Pharmacology Comments
Azithromycin has been investigated as a potential treatment for uncomplicated P. falciparum or P. vivax malaria but does not provide an advantage over current therapies [3].

Potential Target/Mechanism Of Action: As the precise mechanism of action of azithromycin in the malaria parasite is not yet known, we do not have a Plasmodium molecular target for this compound. Further information about possible mechanistic insights is provided under the Clinical data tab.