enoxacin

CHEBI:157175 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A 1,8-naphthyridine derivative that is 1,4-dihydro-1,8-naphthyridine with an ethyl group at the 1 position, a carboxy group at the 3-position, an oxo sustituent at the 4-position, a fluoro substituent at the 5-position and a piperazin-1-yl group at the 7 position. An antibacterial, it is used in the treatment of urinary-tract infections and gonorrhoea. — ChEBI

Classification

fluoroquinolone antibioticARO:0000001

Strictly broader compounds or drug classes this molecule belongs to.

• Label unavailable CHEBI:25384
• Label unavailable CHEBI:33709
• Label unavailable CHEBI:46848
• Label unavailable CHEBI:73537
• quinolone antibiotic CHEBI:86324
• fluoroquinolone antibiotic CHEBI:87211
• fluoroquinolone antibiotic ARO:0000001

Chemical structure

SMILES

CCn1cc(C(=O)O)c(=O)c2cc(F)c(N3CCNCC3)nc21

InChI

InChI=1S/C15H17FN4O3/c1-2-19-8-10(15(22)23)12(21)9-7-11(16)14(18-13(9)19)20-5-3-17-4-6-20/h7-8,17H,2-6H2,1H3,(H,22,23)

Also called

• enoxacine (INN)— chebi
• enoxacino (INN)— chebi
• enoxacinum (INN)— chebi
• 1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid (EXACT_SYNONYM)— chebi
• 1-Ethyl-6-fluoro-4-oxo-7-piperazin-1-yl-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid (EXACT_SYNONYM)— chebi
• 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylic acid (EXACT_SYNONYM)— chebi
• ENOXACIN (EXACT_SYNONYM)— chebi
• Enoxacin (EXACT_SYNONYM)— chebi
• Enroxil (EXACT_SYNONYM)— aro
• Penetrex (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.

• enoxacinARO:0000023
• cas:74011-58-8
• kegg.compound:C06979
• lincs.smallmolecule:LSM-5848
• reaxys:3628995
• vsdb:1896
• chembl:CHEMBL826
• pubchem.compound:3229

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:DB00467
• drugcentral:1013
• kegg.drug:D00310

Patents and articles

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

• patent:EP9425
• patent:US4352803
• patent:US4359578
• wikipedia.en:Enoxacin

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.

fluoroquinolone sensitive gyrA PROTEIN DIRECT_BINDING_TARGET

ARO:3000733

CARD/ARO database assertion; target organism, strain, and assay are not specified. ARO explicitly describes ligand binding to gyrase subunit A. Evidence status: PRIMARY_EVIDENCE_NEEDED. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

• ARO:3000733 (CARD/ARO asserts targeted_by_antibiotic ARO:0000023 (enoxacin); database assertion, not a primary citation.)

Mechanism summary

Mode of action

NUCLEIC_ACID_SYNTHESIS_INHIBITION host shared target — Assigned from ChEBI role CHEBI:59517 (DNA synthesis inhibitor). ChEBI asserts the role on the compound. The target it names is one the host has too, so the mechanism is true but is not evidence of selectivity — see mode_of_action_target_scope. Not a curator's mechanistic review.

Clinical status

APPROVED

Resistance mechanisms

22 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

8. RESEEDED_FROM_SOURCES 2026-10-16 · seed_from_sources

   Re-seeded; changed: resistance_mechanisms (CARD). Upstream retrieval date 2026-08-30, unchanged.

Provenance

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

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