AntibioticMech

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

Classification

imidazole antibioticARO:3007500

Strictly broader compounds or drug classes this molecule belongs to.

• CHEBI:23697 CHEBI:23697
• CHEBI:24780 CHEBI:24780
• CHEBI:36816 CHEBI:36816
• CHEBI:87069 CHEBI:87069
• CHEBI:87071 CHEBI:87071
• ARO:3007500 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

Equivalent identifiers for this same structure in other resources.

• ARO:3007520
• cas:64211-45-6
• drugbank:DB00239
• drugcentral:3408
• hmdb:HMDB0014384
• kegg.compound:C08074
• kegg.drug:D08313
• patent:US4550175
• reaxys:6004213
• wikipedia.en:Oxiconazole
• chembl:CHEMBL1262
• pubchem.compound:5353853

Activity roles

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

• CHEBI:35718 CHEBI:35718
• CHEBI:86327 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

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

Provenance

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