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.
Click here for help

Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

✖

View interactive charts of activity data across species

azithromycin is commercially available from our sponsors

2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
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

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

✖
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
References
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]