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
Bioactivity Comments
Azithromycin, like a number of other antibiotics including doxycycline and clindamycin, kills the malaria parasite in the lifecycle after treatment starts [2]. Consistent with this slow clinical action, the results provided in the interactions table below show that azithromycin is more potent in vitro against erythrocytic stage parasites when assessed two asexual life cycles after the initiation of treatment.
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
motilin receptor Hs Agonist Full agonist 5.5 pEC50 - 1
pEC50 5.5 [1]
Whole organism assay data
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MOA/likely target Sp. Assay description Type Action Value Parameter Concentration range (M) Reference
Unknown MOA PfW2 Ring formation assay (96 hours) - - 7.5 pIC50 - 2
pIC50 7.5 (IC50 3.1x10-8 M) FACS analysis following 96 hours in culture (third-generation rings) [2]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Unknown MOA Pf3D7 Ring formation assay (96 hours) - - 7.3 pIC50 - 2
pIC50 7.3 (IC50 5.27x10-8 M) FACS analysis following 96 hours in culture (third-generation rings) [2]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Unknown MOA PfW2 Ring formation assay (48 hours) - - 5.8 pIC50 - 2
pIC50 5.8 (IC50 1.46x10-6 M) FACS analysis following 48 hours in culture (second-generation rings) [2]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)
Unknown MOA Pf3D7 Ring formation assay (48 hours) - - 5.1 pIC50 - 2
pIC50 5.1 (IC50 8.67x10-6 M) FACS analysis following 48 hours in culture (second-generation rings) [2]
Lifecycle stages: Plasmodium asexual blood stage (erythrocytic merozoite, trophozoite, erythrocytic schizont)