azithromycin   Click here for help

GtoPdb Ligand ID: 6510

Approved drug PDB Ligand Immunopharmacology Ligand Antimalarial Ligand
azithromycin is an approved drug (FDA & UK (1991))
Compound class: Synthetic organic
Comment: Azithromycin is a macrolide antibacterial 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 Organization's Model 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
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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
1. Broad J, Sanger GJ. (2013)
The antibiotic azithromycin is a motilin receptor agonist in human stomach: comparison with erythromycin.
Br J Pharmacol, 168 (8): 1859-67. [PMID:23190027]
2. Dahl EL, Rosenthal PJ. (2007)
Multiple antibiotics exert delayed effects against the Plasmodium falciparum apicoplast.
Antimicrob Agents Chemother, 51 (10): 3485-90. [PMID:17698630]
3. Jaggupilli A, Singh N, De Jesus VC, Gounni MS, Dhanaraj P, Chelikani P. (2019)
Chemosensory bitter taste receptors (T2Rs) are activated by multiple antibiotics.
FASEB J, 33 (1): 501-517. [PMID:30011231]
4. van Eijk AM, Terlouw DJ. (2011)
Azithromycin for treating uncomplicated malaria.
Cochrane Database Syst Rev, (2): CD006688. [PMID:21328286]
5. Zhang Y, Ge L, Song G, Zhang R, Li S, Shi H, Zhang H, Li Y, Pan J, Wang L et al.. (2022)
Azithromycin alleviates the severity of rheumatoid arthritis by targeting the unfolded protein response component of glucose-regulated protein 78 (GRP78).
Br J Pharmacol, 179 (6): 1201-1219. [PMID:34664264]