azithromycin

Ligand id: 6510

Name: azithromycin

Structure and Physico-chemical Properties

2D Structure
Calculated Physico-chemical Properties
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

Molecular properties generated using the CDK

Classification
Compound class Synthetic organic
Ligand families/groups Antimalarial ligands
Approved drug? Yes (FDA & UK (1991))
IUPAC Name
(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-[(2S,3R,4S,6R)-4-dimethylamino-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one
International Nonproprietary Names
INN number INN
6197 azithromycin
Comments
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 key antibacterials in the WHO 20th Essential Medicines List (2017).

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
Database Links
CAS Registry No. 83905-01-5 (source: Scifinder)
ChEMBL Ligand CHEMBL529
DrugBank Ligand DB00207
GtoPdb PubChem SID 178103124
PubChem CID 447043
RCSB PDB Ligand ZIT
Search Google for chemical match using the InChIKey MQTOSJVFKKJCRP-BICOPXKESA-N
Search Google for chemicals with the same backbone MQTOSJVFKKJCRP
Search PubMed clinical trials azithromycin
Search PubMed titles azithromycin
Search PubMed titles/abstracts azithromycin
Search UniChem for chemical match using the InChIKey MQTOSJVFKKJCRP-BICOPXKESA-N
Search UniChem for chemicals with the same backbone MQTOSJVFKKJCRP
Wikipedia Azithromycin

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Tocris
Azithromycin
Cat. No. 3771