AntibioticMech

cinoxacin

CHEBI:3716 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A member of the class of cinnolines that is 6,7-methylenedioxycinnolin-4(1H)-one bearing an ethyl group at position 1 and a carboxylic acid group at position 3. An analogue of oxolinic acid, it has similar antibacterial actions. It was formerly used for the treatment of urinary tract infections. — ChEBI

Classification

fluoroquinolone antibioticARO:0000001

Strictly broader compounds or drug classes this molecule belongs to.

• CHEBI:25754 CHEBI:25754
• CHEBI:38104 CHEBI:38104
• CHEBI:38770 CHEBI:38770
• ARO:0000001 ARO:0000001

Chemical structure

Computed structure properties

Molecular formula	C12H10N2O5
Charge	0
Average mass	262.221 Da
Monoisotopic mass	262.05897 Da
Source	ChEBI
InChIKey	VDUWPHTZYNWKRN-UHFFFAOYSA-N

SMILES

CCn1nc(C(=O)O)c(=O)c2cc3c(cc21)OCO3

InChI

InChI=1S/C12H10N2O5/c1-2-14-7-4-9-8(18-5-19-9)3-6(7)11(15)10(13-14)12(16)17/h3-4H,2,5H2,1H3,(H,16,17)

Also called

• cinoxacine (INN)— chebi
• cinoxacino (INN)— chebi
• cinoxacinum (INN)— chebi
• 1-ethyl-4-oxo-1,4-dihydro[1,3]dioxolo[4,5-g]cinnoline-3-carboxylic acid (EXACT_SYNONYM)— chebi
• 1-ethyl-6,7-methylenedioxy-4(1H)-oxocinnoline-3-carboxylic acid (EXACT_SYNONYM)— chebi
• 5-Ethyl-8-oxo-5,8-dihydro-1,3-dioxa-5,6-diaza-cyclopenta[b]naphthalene-7-carboxylic acid (EXACT_SYNONYM)— chebi
• Azolinic acid (EXACT_SYNONYM)— aro
• CIN (EXACT_SYNONYM)— aro

Cross-references

Equivalent identifiers for this same structure in other resources.

• ARO:3004010
• beilstein:1084304
• cas:28657-80-9
• drugbank:DB00827
• drugcentral:657
• hmdb:HMDB0014965
• kegg.drug:D00872
• lincs.smallmolecule:LSM-6552
• patent:DE2005104
• patent:US3669965
• patent:US6441167
• vsdb:1881
• wikipedia.en:Cinoxacin
• chembl:CHEMBL1208
• pubchem.compound:2762

Activity roles

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

• 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:3004010	cinoxacin	antibioticmech:aro-6d374595e4	2026-08-30
CHEBI	CHEBI:3716	cinoxacin	antibioticmech:chebi-0866fa0c6d	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.

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:3004010 (cinoxacin); database assertion, not a primary citation.)

fluoroquinolone sensitive gyrB PROTEIN DIRECT_BINDING_TARGET

ARO:3003261

CARD/ARO database assertion; target organism, strain, and assay are not specified. GyrB is asserted as the fluoroquinolone-sensitive subunit. Evidence status: PRIMARY_EVIDENCE_NEEDED. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

• ARO:3003261 (CARD/ARO asserts targeted_by_antibiotic ARO:3004010 (cinoxacin); database assertion, not a primary citation.)

Mechanism summary

Clinical status

APPROVED

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

Provenance

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