Structure via PubChem · Public domain (PubChem)
oxiconazole
Sign in to saveAlso known as Oxiconazol, Oxiconazolum, Ro 13-8996, 2',4'-Dichloro-2-imidazol-1-ylacetophenone (Z)-[O-(2,4-dichlorobenzyl)oxime]
Oxiconazole (trade names Oxistat in the US, Oxizole in Canada) is an antifungal medication typically administered in a cream or lotion to treat skin infections, such as athlete's foot, jock itch and ringworm. It can also be prescribed to treat the skin rash known as tinea versicolor, caused by systemic yeast overgrowth (Candida spp.).
Chemical data
- Formula
- C18H13Cl4N3O
- Molecular weight
- 429.1 g/mol
- IUPAC name
- (Z)-1-(2,4-dichlorophenyl)-N-[(2,4-dichlorophenyl)methoxy]-2-imidazol-1-ylethanimine
- SMILES
- C1=CC(=C(C=C1Cl)Cl)CO/N=C(\CN2C=CN=C2)/C3=C(C=C(C=C3)Cl)Cl
- InChIKey
- QRJJEGAJXVEBNE-HKOYGPOVSA-N
- XLogP
- 6.1
- Polar surface area
- 39.4 Ų
- H-bond donors
- 0
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1988
- Admin. routes
- topical
via ChEMBL · EBI
Research
128 papers- Oxiconazole.2006
- Oxiconazole Potentiates Gentamicin against Gentamicin-Resistant Staphylococcus aureus In Vitro and In Vivo.Microbiology spectrum · 2023
- Repurposing oxiconazole to inhibit STING trafficking via OSBP and alleviate autoimmune pathology in Trex1(-/-) mice.International immunopharmacology · 2025
- Repurposing Oxiconazole against Colorectal Cancer via PRDX2-mediated Autophagy Arrest.International journal of biological sciences · 2022
- Oxiconazole nitrate: pharmacology, efficacy, and safety of a new imidazole antifungal agent.Clinical therapeutics · 1991
via PubMed
Wikidata facts
- Subclass of
- azole
- Mass
- 426.981272756
- Has use
- medication
Show 7 more facts
- Commons category
- Oxiconazole
- chemical formula
- C₁₈H₁₃Cl₄N₃O
- medical condition treated
- tinea cruris
- canonical SMILES
- C1=CC(=C(C=C1Cl)Cl)CON=C(CN2C=CN=C2)C3=C(C=C(C=C3)Cl)Cl
- isomeric SMILES
- C1=CC(=C(C=C1Cl)Cl)CO/N=C(\CN2C=CN=C2)/C3=C(C=C(C=C3)Cl)Cl
- subject has role
- antifungal
- World Health Organisation international non-proprietary name
- oxiconazole
via Wikidata · CC0
~1 min read
Encyclopedic overview
4 sectionsContents
- Synthesis
- See also
- References
- External links
Oxiconazole (trade names Oxistat in the US, Oxizole in Canada) is an antifungal medication typically administered in a cream or lotion to treat skin infections, such as athlete's foot, jock itch and ringworm. It can also be prescribed to treat the skin rash known as tinea versicolor, caused by systemic yeast overgrowth (Candida spp.).
It was patented in 1975 and approved for medical use in 1983. ==Synthesis== upright=2 Treatment of the ketone (1) with hydroxylamine gives the oxime (2), which is alkylated with 2,4-dichlorobenzyl chloride (3) in the presence of the strong base sodium hydride to give oxiconazole.
Excerpted from Wikipedia’s “oxiconazole” article, available under the CC BY-SA 4.0 licence.