oxiconazole

CHEBI:7825 ·resolve ·ANTIFUNGAL ·EXACT SEEDED

An oxime O-ether that is the 2,4-dichlorobenzyl ether of the oxime obtained by formal condensation of hydroxylamine with the carbonyl group of acetopnenone in which the phenyl group is substituted by chlorines at positions 2 and 4, and in which one of the hydrogens of the methyl group is replaced by a 1H-imidazol-1-yl group. An antifungal agent, it is used (generally as the nitrate salt) in creams and powders for the topical treatment of fungal skin 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

imidazole antibioticARO:3007500

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:23697
Label unavailable CHEBI:24780
Label unavailable CHEBI:36816
imidazole antifungal drug CHEBI:87069
conazole antifungal drug CHEBI:87071
imidazole antibiotic ARO:3007500

Chemical structure

Computed structure properties
Molecular formula	C18H13Cl4N3O
Charge	0
Average mass	429.134 Da
Monoisotopic mass	426.98127 Da
Source	ChEBI
InChIKey	QRJJEGAJXVEBNE-HKOYGPOVSA-N

SMILES

Clc1ccc(CO/N=C(\Cn2ccnc2)c2ccc(Cl)cc2Cl)c(Cl)c1

InChI

InChI=1S/C18H13Cl4N3O/c19-13-2-1-12(16(21)7-13)10-26-24-18(9-25-6-5-23-11-25)15-4-3-14(20)8-17(15)22/h1-8,11H,9-10H2/b24-18+

Also called

oxiconazol (INN)— chebi
oxiconazolum (INN)— chebi
(1Z)-N-[(2,4-dichlorobenzyl)oxy]-1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanimine (EXACT_SYNONYM)— chebi
2',4'-Dichloro-2-imidazol-1-ylacetophenone (Z)-[O-(2,4-dichlorobenzyl)oxime] (EXACT_SYNONYM)— chebi
Ro 13-8996 (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.

Activity roles

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

antifungal agent CHEBI:35718
antifungal drug CHEBI:86327

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:3007520`	oxiconazole	`antibioticmech:aro-511831d088`	2026-08-30
CHEBI	`CHEBI:7825`	oxiconazole	`antibioticmech:chebi-65e420af8d`	2026-08-30

Mechanism summary

Mode of action: ERGOSTEROL_PATHWAY_INHIBITION host shared target — Assigned from ChEBI role CHEBI:75282 (ergosterol biosynthesis 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.

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 2026-09-10 · 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).

Explore across X-Mech: MediaIngredientMech (oxiconazole) · CultureMech · NaturalProductMech · PathwayMech · TraitMech