Oxiconazole

Chemical compound

D01AC11 (WHO) G01AF17 (WHO)

Identifiers

IUPAC name

(E)-[1-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-yl)ethylidene] [(2,4-dichlorophenyl)methoxy]amine

CAS Number

64211-46-7^Y

PubChem CID

5361463

DrugBank

DB00239^Y

ChemSpider

4514745^Y

UNII

RQ8UL4C17S

KEGG

D00885^Y

ChEBI

CHEBI:7825^N

ChEMBL

ChEMBL1262^N

CompTox Dashboard (EPA)

DTXSID8040690

Chemical and physical dataFormulaC₁₈H₁₃Cl₄N₃OMolar mass429.12 g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

Clc3ccc(/C(=N\OCc1ccc(Cl)cc1Cl)Cn2ccnc2)c(Cl)c3

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-^Y
Key:QRJJEGAJXVEBNE-MOHJPFBDSA-N^Y

^NY (what is this?) (verify)

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.^[1]

References

^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 503. ISBN 9783527607495.

External links

MedlinePlus - Oxiconazole

Antifungals (D01 and J02)

Wall/
membrane

Ergosterol
inhibitors

Azoles (lanosterol 14α-
demethylase inhibitors)

Imidazoles	Topical: bifonazole^‡ butoconazole chlormidazole^‡ climbazole clotrimazole^# croconazole^‡ eberconazole econazole fenticonazole^‡ flutrimazole isoconazole ketoconazole luliconazole miconazole^# neticonazole^‡ omoconazole^‡ oxiconazole sertaconazole sulconazole tioconazole Systemic: ketoconazole
Triazoles	Topical: efinaconazole fluconazole^# terconazole Systemic: fluconazole^# fosfluconazole fosravuconazole hexaconazole^‡ isavuconazole itraconazole^# oteseconazole posaconazole voriconazole^# Unknown: albaconazole^‡ ravuconazole^†
Thiazoles	Topical: abafungin^‡

Polyene antimycotics
(ergosterol binding)

Topical: hamycin^‡
natamycin
nystatin^#
Systemic: amphotericin B^#, hamycin^‡

Squalene monooxygenase
inhibitors

Allylamines	Topical: naftifine terbinafine Systemic: terbinafine
Benzylamines	Topical: butenafine

Others

Topical: amorolfine

β-glucan synthase
inhibitors

Intracellular

Pyrimidine analogues/ thymidylate synthase inhibitors	Systemic: flucytosine^#
Mitotic inhibitors	Systemic: griseofulvin^#
Aminoacyl tRNA synthetase inhibitors	Topical: tavaborole

Others

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Gynecological anti-infectives and antiseptics (G01)

Antibiotics

Arsenic compounds

Acetarsol

Quinoline derivatives

Organic acids

Sulfonamides

Sulfatolamide

Antifungals

Imidazoles	Metronidazole Clotrimazole Miconazole Econazole Ornidazole Isoconazole Tioconazole Ketoconazole Fenticonazole Azanidazole Propenidazole Butoconazole Omoconazole Oxiconazole Flutrimazole
Triazoles	Terconazole
Polyenes	Nystatin Natamycin Amphotericin B
Other	Ciclopirox Methylrosaniline