cethromycin

CHEBI:29506 ·resolve ·ANTIBACTERIAL ·EXACT REVIEWED

A macrolide antibiotic which displays in vitro activity against both gram-positive and gram-negative bacteria and is currently under investigation for the treatment of community-acquired pneumonia. The US Food and Drug Administration (FDA) have also granted orphan drug designation to cethromycin for the treatment of anthrax prophylaxis, tularemia, and plague (PDB entry: <a href="https://www.ebi.ac.uk/pdbe/entry/pdb/1NWX" target="_blank">1NWX</a>). — ChEBI

Classification

macrolide antibioticARO:0000000

Strictly broader compounds or drug classes this molecule belongs to.

macrolide antibiotic CHEBI:25105
Label unavailable CHEBI:26513
Label unavailable CHEBI:63367
macrolide antibiotic ARO:0000000

Chemical structure

Computed structure properties
Molecular formula	C42H59N3O10
Charge	0
Average mass	765.945 Da
Monoisotopic mass	765.42005 Da
Source	ChEBI
InChIKey	PENDGIOBPJLVBT-AMXFZXBBSA-N

SMILES

[H]C(CO[C@]1(C)C[C@@H](C)C(=O)[C@H](C)[C@H]2NC(=O)O[C@]2(C)[C@@H](CC)OC(=O)[C@H](C)C(=O)[C@H](C)[C@H]1O[C@@H]1O[C@H](C)C[C@H](N(C)C)[C@H]1O)=C([H])c1cnc2ccccc2c1

InChI

InChI=1S/C42H59N3O10/c1-11-32-42(8)36(44-40(50)55-42)25(4)33(46)23(2)21-41(7,51-18-14-15-28-20-29-16-12-13-17-30(29)43-22-28)37(26(5)34(47)27(6)38(49)53-32)54-39-35(48)31(45(9)10)19-24(3)52-39/h12-17,20,22-27,31-32,35-37,39,48H,11,18-19,21H2,1-10H3,(H,44,50)/t23-,24-,25+,26+,27-,31+,32-,35-,36-,37-,39+,41-,42-/m1/s1

Also called

Restanza (BRAND_NAME)— chebi
cethromycinum (INN)— chebi
cetromicina (INN)— chebi
céthromycine (INN)— chebi
(3aS,4R,7R,9R,10R,11R,13R,15R,15aR)-4-ethyl-3a,7,9,11,13,15-hexamethyl-2,6,8,14-tetraoxo-11-{[3-(quinolin-3-yl)prop-2-en-1-yl]oxy}tetradecahydro-2H-oxacyclotetradecino[4,3-d][1,3]oxazol-10-yl 3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranoside (EXACT_SYNONYM)— chebi
A-195773 (EXACT_SYNONYM)— chebi
ABT-773 (EXACT_SYNONYM)— chebi
Abbott-195773 (EXACT_SYNONYM)— chebi

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.

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.

Patents and articles

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

wikipedia.en:Cethromycin

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.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
ARO	`ARO:3007455`	cethromycin	`antibioticmech:aro-05fd3c6113`	2026-08-30
CHEBI	`CHEBI:29506`	cethromycin	`antibioticmech:chebi-eabf9838f5`	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 nascent-peptide exit tunnel RIBOSOMAL_SUBUNIT DIRECT_BINDING_TARGET

A D. radiodurans large-subunit cocrystal localized ABT-773 in the protein exit tunnel; H. influenzae translation and isolated-ribosome assays measured inhibition, affinity, and slow dissociation. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 2003-03; 2004-10 (retrieved 2026-09-02).

PMID:12623020 (Primary ABT-773-bound bacterial ribosome structural study (PDB:1NWX; DOI:10.1016/S0969-2126(03)00022-4).)
PMID:15380262 (Primary H. influenzae translation and ribosome-affinity study (DOI:10.1016/j.ijantimicag.2004.04.013).)

Mechanism summary

Mode of action: PROTEIN_SYNTHESIS_INHIBITION host shared target — CURATOR: PMID:12623020 determined the Deinococcus radiodurans 50S ribosomal-subunit structure with ABT-773 (cethromycin) bound in the nascent-peptide exit tunnel. PMID:15380262 independently measured protein-synthesis inhibition and tight, slowly dissociating binding to Haemophilus influenzae ribosomes.

Record-level evidence

PMID:12623020 (Primary cethromycin-bound bacterial ribosome structural study.)
PMID:15380262 (Primary cethromycin ribosome-affinity and translation study.)

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
REVIEWED 2026-09-02 · codex · LLM-assisted
Verified exact ChEBI/CARD identity, structure, roles, structural class, and antibacterial class; replaced the seeded mechanism note with primary evidence and added the directly bound bacterial 50S exit-tunnel target.
RESEEDED_FROM_SOURCES 2026-09-10 · 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 (YAML).

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