azithromycin

CHEBI:2955 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

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

Classification

macrolide antibioticARO:0000000

Strictly broader compounds or drug classes this molecule belongs to.

• macrolide antibiotic CHEBI:25105
• macrolide antibiotic ARO:0000000

Chemical structure

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

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

• azithromycinARO:3000158
• cas:83905-01-5
• hmdb:HMDB0014352
• kegg.compound:C06838
• lincs.smallmolecule:LSM-5821
• pdb-ccd:ZIT
• reaxys:5387583
• reaxys:8820027
• chembl:CHEMBL529
• pubchem.compound:447043

Drug registries

Identifiers that name a drug rather than a structure. One of these can cover a parent compound, its salts and its stereoisomers, which this corpus keeps as separate records, so it is not an equivalence of structure.

• drugbank:DB00207
• drugcentral:276
• kegg.drug:D07486

Patents and articles

Documents about this compound. A patent covers a class and an article covers a topic; neither identifies a structure.

• patent:BE892357
• patent:US4517359
• wikipedia.en:Azithromycin

Activity roles

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

• antimicrobial agent CHEBI:33281
• antibacterial drug 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.

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.)

Activity spectrum

Measured or curated activity against specific taxa. A number without a method is not an observation — every row here carries an assay.

2 observations · Browse all observations · Complete record (JSON.gz)

Resistance mechanisms

55 source-backed resistance determinants or associations, with ARO grounding where reported. Grouped by reported mechanism type.

Curation history

1. SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Seeded from data/raw/ inventories (ARO, CHEBI)

2. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

3. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

4. RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

5. RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

6. CURATED_RESISTANT_TAXA 2026-09-13 · codex · LLM-assisted

   Added one stable-URL CDC/FDA AR Isolate Bank Panel 10 azithromycin-resistant Neisseria gonorrhoeae activity observation for AR-1281.

7. STRUCTURED_ACTIVITY_BIOSAMPLE_ACCESSIONS 2026-09-26 · codex · LLM-assisted

   Structured BioSample accessions on 1 activity_spectrum observation(s) where evidence notes already named exactly one accession.

8. RESEEDED_FROM_SOURCES 2026-09-26 · seed_from_sources

   Re-seeded; changed: activity_spectrum (CRYPTIC 3.4.0). Upstream retrieval date 2026-08-30, unchanged.

9. RESEEDED_FROM_SOURCES 2026-10-05 · seed_from_sources

   Re-seeded; changed: activity_membership_collections (CRYPTIC 3.4.0). Upstream retrieval date 2026-08-30, unchanged.

10. CURATED_RESISTANCE_EVIDENCE 2026-10-10 · codex · LLM-assisted

    Added one native Epi0082 mef(F)/msr(G) and azithromycin co-occurrence claim with verified species-name and source-reported genome-component context. Kept the different-species UniProt reference and expression-host experiment separate; preserved every source-owned claim and membership. Whole-record review remains open.

Provenance

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

Explore across X-Mech: MediaIngredientMech (azithromycin) · CultureMech · NaturalProductMech · PathwayMech · TraitMech