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

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

fluoroquinolone antibioticARO:0000001

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:25754
Label unavailable CHEBI:38104
Label unavailable CHEBI:38770
fluoroquinolone antibiotic 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

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.

Activity roles

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

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: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

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
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
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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