dirithromycin

CHEBI:474014 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

The hemi-aminal resulting from the condensation of the erythromycin derivative (9S)-erythromycyclamine with 2-(2-methoxyethoxy)acetaldehyde. As the oxazine ring containing the hemi-aminal group is unstable under both acidic and alkaline conditions, dirithromycin functions as a more lipid-soluble prodrug for (9S)-erythromycyclamine. Administered as enteric coated tablets to protect it from acid catalysed hydrolysis in the stomach, it is used to treat respiratory tract, skin, and soft tissue infections caused by susceptible organisms. — 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)[C@@H]2N[C@@H](COCCOC)O[C@H]([C@H]2C)[C@]1(C)O

InChI

InChI=1S/C42H78N2O14/c1-15-29-42(10,49)37-24(4)32(43-30(56-37)21-52-17-16-50-13)22(2)19-40(8,48)36(58-39-33(45)28(44(11)12)18-23(3)53-39)25(5)34(26(6)38(47)55-29)57-31-20-41(9,51-14)35(46)27(7)54-31/h22-37,39,43,45-46,48-49H,15-21H2,1-14H3/t22-,23-,24+,25+,26-,27+,28+,29-,30-,31+,32+,33-,34+,35+,36-,37-,39+,40-,41-,42-/m1/s1

Also called

• dirithromycine (INN)— chebi
• dirithromycinum (INN)— chebi
• diritromicina (INN)— chebi
• (1R,2R,3R,6R,7S,8S,9R,10R,12R,13S,15R,17S)-3-ethyl-2,10-dihydroxy-15-[(2-methoxyethoxy)methyl]-2,6,8,10,12,17-hexamethyl-5-oxo-9-{[3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyl]oxy}-4,16-dioxa-14-azabicyclo[11.3.1]heptadec-7-yl 2,6-dideoxy-3-C-methyl-3-O-methyl-α-L-ribo-hexopyranoside (EXACT_SYNONYM)— chebi
• (9S)-9-deoxo-11-deoxy-9,11-(imino((1R)-2-(2-methoxyethoxy)ethylidene)oxy)erythromycin (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.

• dirithromycinARO:3000176
• beilstein:4225019
• cas:62013-04-1
• lincs.smallmolecule:LSM-5636
• chembl:CHEMBL1237072
• pubchem.compound:6473883

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:DB00954
• drugcentral:925
• kegg.drug:D03865

Patents and articles

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

• patent:BE840431
• patent:US4048306
• wikipedia.en:Dirithromycin

Activity roles

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

• antimicrobial agent CHEBI:33281

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:3000176 (dirithromycin); database assertion, not a primary citation.)

Mechanism summary

Clinical status

APPROVED

Resistance mechanisms

23 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 2026-08-31 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

6. RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

7. 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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