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Azithromycin
Azithromycin
2D structure of azithromycin
Azithromycin ball and stick
3D structure of azithromycin
Names
Synonyms Azithromycine, CP-62993, XZ-450
Brand names Azith, Zedd, Zithromax, Zitrocin and others

IUPAC name
IUPAC name
(2R,3S,4R,5R,8R,10R,11R,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
Clinical information
Preg. cat.
AU: B1
US: B
Legal status
AU: Prescription Only Medicine (S4)
CA: ℞-only
UK: POM
US: ℞-only
Routes Intravenous, opthalmic, oral


Identifiers
ATC code J01FA10
ChemSpider 10482163
DrugBank DB00207
PubChem 55185
MedlinePlus a697037
MeSH ID D017963
PDB IDs
PDBs
1M1K (RCSB, PDBe; X-ray)
1NWY (RCSB, PDBe; X-ray)
1YHQ (RCSB, PDBe; X-ray)
3OT1 (RCSB, PDBe; X-ray)
3OHZ (RCSB, PDBe; X-ray)
External links
DailyMed azithromycin search
Drugs.com international, monograph
Jmol 3D structure
Licensing data US FDA: link.
MSR monograph
emc azithromycin search
TGA-eBS azithromycin search
Chemical properties
Formula C38H72N2O12
Mol. mass
Mol. mass for MFs
748.98448 g/mol
SMILES
SMILES
CC[C@@H]1[C@@]([C@@H]([C@H](N(C[C@@H](C[C@@]([C@@H](C([C@@H]([C@H](C(=O)O1)C)O[C@H]2C[C@@]([C@H]([C@@H](O2)C)O)(C)OC)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)(C)O)C)C)C)O)(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
InChIKey
InChIKey
MQTOSJVFKKJCRP-OHJWJPDZSA-N


Azithromycin is a macrolide antibiotic that is widely used in the management of bacterial infections, including: pneumonia, chlamydia, streptococcal pharyngitis/tonsillitis, parathyroid/thyroid fever, whooping cough (pertussis), traveller's diarrhoea and Mycobacterium avium complex infections.[1] It is on the World Health Organization's List of Essential Medicines.[2]



External linksEdit

Reference listEdit

  1. Rossi, S, ed. (July 2014). "Azithromycin". Australian Medicines Handbook. Adelaide, Australia: Australian Medicines Handbook Pty Ltd. Retrieved 5 December 2014. 
  2. World Health Organization (October 2013). "WHO Model List of Essential Medicines 18th list" (PDF). who.int. Geneva, Switzerland: World Health Organization. Retrieved 5 December 2014. 

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