CHEBI:2955 - azithromycin

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ChEBI Name azithromycin
ChEBI ID CHEBI:2955
Definition A macrolide antibiotic useful for the treatment of bacterial infections.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:46596
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Formula C38H72N2O12
Net Charge 0
Average Mass 748.98450
Monoisotopic Mass 748.50853
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 MQTOSJVFKKJCRP-BICOPXKESA-N
SMILES CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@](C)(O)C[C@@H](C)CN(C)[C@H](C)[C@@H](O)[C@]1(C)O
Roles Classification
Chemical Role(s): environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
Biological Role(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
xenobiotic
A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via macrolide antibiotic )
Application(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing azithromycin (CHEBI:2955) has role antibacterial drug (CHEBI:36047)
azithromycin (CHEBI:2955) has role environmental contaminant (CHEBI:78298)
azithromycin (CHEBI:2955) has role xenobiotic (CHEBI:35703)
azithromycin (CHEBI:2955) is a macrolide antibiotic (CHEBI:25105)
azithromycin (CHEBI:2955) is conjugate base of azithromycin(2+) (CHEBI:231550)
Incoming azithromycin dihydrate (CHEBI:34546) has part azithromycin (CHEBI:2955)
azithromycin(2+) (CHEBI:231550) is conjugate acid of azithromycin (CHEBI:2955)
IUPAC Name
(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-2-ethyl-3,4,10-trihydroxy-3,5,6,8,10,12,14-heptamethyl-15-oxo-11-{[3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyl]oxy}-1-oxa-6-azacyclopentadecan-13-yl 2,6-dideoxy-3-C-methyl-3-O-methyl-α-L-ribo-hexopyranoside
INNs Sources
azithromycine ChemIDplus
azithromycinum ChemIDplus
azitromicina WHO MedNet
Synonym Source
(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)13-((2,6-Dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranosyl)oxy)-2-ethyl-3,4,10-trihydroxy-3,5,6,8,10,12,14-heptamethyl-11-((3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl)oxy)-1-oxa-6-azacyclopentadecan-15-one ChemIDplus
Brand Names Sources
Azenil DrugBank
Azifast ChEBI
Azigram ChEBI
Azimakrol ChEBI
Azitromin ChEBI
Hemomycin DrugBank
Zithromax DrugBank
Zmax DrugBank
Manual Xrefs Databases
276 DrugCentral
Azithromycin Wikipedia
BE892357 Patent
C06838 KEGG COMPOUND
D07486 KEGG DRUG
DB00207 DrugBank
HMDB0014352 HMDB
LSM-5821 LINCS
US4517359 Patent
ZIT PDBeChem
View more database links
Registry Numbers Types Sources
5387583 Reaxys Registry Number Reaxys
83905-01-5 CAS Registry Number ChemIDplus
8820027 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
15143799 PubMed citation Europe PMC
18253999 PubMed citation Europe PMC
Last Modified
11 June 2024
General Comment
2014-10-29 Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag