azithromycin

CHEBI:2955 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A macrolide antibiotic useful for the treatment of bacterial infections. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

macrolide antibioticARO:0000000

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:25105 CHEBI:25105
ARO:0000000 ARO:0000000

Chemical structure

Computed structure properties
Molecular formula	C38H72N2O12
Charge	0
Average mass	748.996 Da
Monoisotopic mass	748.50853 Da
Source	ChEBI
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](N(C)C)[C@H]2O)[C@](C)(O)C[C@@H](C)CN(C)[C@H](C)[C@@H](O)[C@]1(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

Also called

Azenil (BRAND_NAME)— chebi
Azifast (BRAND_NAME)— chebi
Azigram (BRAND_NAME)— chebi
Azimakrol (BRAND_NAME)— chebi
Azitromin (BRAND_NAME)— chebi
Hemomycin (BRAND_NAME)— chebi
Zithromax (BRAND_NAME)— chebi
Zmax (BRAND_NAME)— chebi
azithromycine (INN)— chebi
azithromycinum (INN)— chebi
azitromicina (INN)— chebi
(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 (EXACT_SYNONYM)— chebi
(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 (EXACT_SYNONYM)— chebi
AZM (EXACT_SYNONYM)— aro

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:3000158
cas:83905-01-5
drugbank:DB00207
drugcentral:276
hmdb:HMDB0014352
kegg.compound:C06838
kegg.drug:D07486
lincs.smallmolecule:LSM-5821
patent:BE892357
patent:US4517359
pdb-ccd:ZIT
reaxys:5387583
reaxys:8820027
wikipedia.en:Azithromycin
chembl:CHEMBL529
pubchem.compound:447043

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

CHEBI:33281 CHEBI:33281
CHEBI:36047 CHEBI:36047

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
ARO	`ARO:3000158`	azithromycin	`antibioticmech:aro-904736d7d5`	2026-08-30
CHEBI	`CHEBI:2955`	azithromycin	`antibioticmech:chebi-8c555420d7`	2026-08-30

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

50S ribosomal subunit P-site RIBOSOMAL_SUBUNIT DIRECT_BINDING_TARGET

ARO:3000757

CARD/ARO database assertion; target organism, strain, and assay are not specified. The 50S P-site is asserted as the target site. Evidence status: PRIMARY_EVIDENCE_NEEDED. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

ARO:3000757 (CARD/ARO asserts targeted_by_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)

Resistance mechanisms

54 known routes by which microbes resist this compound, grounded in ARO where CARD models them. Grouped by mechanism type — expand a group to see its determinants.

ANTIBIOTIC_TARGET_ALTERATION 32

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
Chlamydia trachomatis 23S rRNA with mutation conferring resistance to macrolide antibiotics	ARO:3004174	not organism-specific	—	ARO:3004174 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
Erm(33)	ARO:3000599	not organism-specific	—	ARO:3000599 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
Erm(34)	ARO:3000600	not organism-specific	—	ARO:3000600 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
Erm(35)	ARO:3000604	not organism-specific	—	ARO:3000604 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
Erm(36)	ARO:3000605	not organism-specific	—	ARO:3000605 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
Erm(37)	ARO:3000392	not organism-specific	—	ARO:3000392 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
Erm(38)	ARO:3000601	not organism-specific	—	ARO:3000601 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
Erm(39)	ARO:3000602	not organism-specific	—	ARO:3000602 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
Erm(41)	ARO:3000603	not organism-specific	—	ARO:3000603 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
Erm(47)	ARO:3003908	not organism-specific	—	ARO:3003908 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
Erm(51)	ARO:3007033	not organism-specific	—	ARO:3007033 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
ErmA	ARO:3000347	not organism-specific	—	ARO:3000347 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
ErmB	ARO:3000375	not organism-specific	—	ARO:3000375 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
ErmC	ARO:3000250	not organism-specific	—	ARO:3000250 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
ErmD	ARO:3000495	not organism-specific	—	ARO:3000495 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
ErmE	ARO:3000326	not organism-specific	—	ARO:3000326 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
ErmF	ARO:3000498	not organism-specific	—	ARO:3000498 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
ErmG	ARO:3000522	not organism-specific	—	ARO:3000522 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
ErmN	ARO:3000592	not organism-specific	—	ARO:3000592 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
ErmQ	ARO:3000593	not organism-specific	—	ARO:3000593 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
ErmR	ARO:3000594	not organism-specific	—	ARO:3000594 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
ErmT	ARO:3000595	not organism-specific	—	ARO:3000595 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
ErmX	ARO:3000596	not organism-specific	—	ARO:3000596 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
ErmY	ARO:3002825	not organism-specific	—	ARO:3002825 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
Moraxella catarrhalis 23S rRNA with mutation conferring resistance to macrolide antibiotics	ARO:3004138	not organism-specific	—	ARO:3004138 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
Mycobacterium intracellulare 23S rRNA with mutation conferring resistance to azithromycin	ARO:3004167	not organism-specific	—	ARO:3004167 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
Mycoplasma genitalium 23S rRNA mutations confers resistance to fluoroquinolone and macrolide antibiotics	ARO:3004616	not organism-specific	—	ARO:3004616 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
Mycoplasma hominis 23S rRNA with mutation conferring resistance to macrolide antibiotics	ARO:3004176	not organism-specific	—	ARO:3004176 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
Neisseria gonorrhoeae 23S rRNA with mutation conferring resistance to azithromycin	ARO:3004836	not organism-specific	—	ARO:3004836 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
Neisseria gonorrhoeae rpld	ARO:3004956	not organism-specific	—	ARO:3004956 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
erm(46)	ARO:3004596	not organism-specific	—	ARO:3004596 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
erm(55)	ARO:3009647	not organism-specific	—	ARO:3009647 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)

ANTIBIOTIC_INACTIVATION 11

ANTIBIOTIC_INACTIVATION
Determinant	ARO ID	Organism	Gene families	Evidence
EreB	ARO:3000363	not organism-specific	—	ARO:3000363 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
Mrx	ARO:3003839	not organism-specific	—	ARO:3003839 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
mgtA	ARO:3000462	not organism-specific	—	ARO:3000462 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
mphA	ARO:3000316	not organism-specific	—	ARO:3000316 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
mphB	ARO:3000318	not organism-specific	—	ARO:3000318 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
mphC	ARO:3000319	not organism-specific	—	ARO:3000319 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
mphF	ARO:3003071	not organism-specific	—	ARO:3003071 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
mphG	ARO:3003742	not organism-specific	—	ARO:3003742 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
mphH	ARO:3004539	not organism-specific	—	ARO:3004539 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
mphK	ARO:3004541	not organism-specific	—	ARO:3004541 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
mphL	ARO:3003072	not organism-specific	—	ARO:3003072 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)

ANTIBIOTIC_EFFLUX 10

ANTIBIOTIC_EFFLUX
Determinant	ARO ID	Organism	Gene families	Evidence
AmrAB-OprM	ARO:3002981	not organism-specific	—	ARO:3002981 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
Klebsiella pneumoniae KpnGH-TolC	ARO:3004598	not organism-specific	—	ARO:3004598 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
LpeAB	ARO:3004098	not organism-specific	—	ARO:3004098 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
MexAB-OprM	ARO:3000386	not organism-specific	—	ARO:3000386 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
MtrCDE	ARO:3000369	not organism-specific	—	ARO:3000369 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
Neisseria gonorrhoeae mtrR with mutation conferring resistance	ARO:3004851	not organism-specific	—	ARO:3004851 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
lmrP	ARO:3003969	not organism-specific	—	ARO:3003969 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
mef(B)	ARO:3003107	not organism-specific	—	ARO:3003107 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
mef(F)	ARO:3007044	not organism-specific	—	ARO:3007044 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)
mreA	ARO:3007050	not organism-specific	—	ARO:3007050 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)

ANTIBIOTIC_TARGET_PROTECTION 1

ANTIBIOTIC_TARGET_PROTECTION
Determinant	ARO ID	Organism	Gene families	Evidence
msr(G)	ARO:3007042	not organism-specific	—	ARO:3007042 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000158 (azithromycin); database assertion, not a primary citation.)

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (ARO, CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record.