Oxiconazole

Names

[ Name ]:
Oxiconazole

[Synonym ]:
oxyconazole
Oxiconazolum [INN-Latin]
(Z)-1-(2,4-dichlorophenyl)-N-[(2,4-dichlorophenyl)methoxy]-2-imidazol-1-ylethanimine
Ethanone, 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)-, O-[(2,4-dichlorophenyl)methyl]oxime, (1Z)-
Oxiconazole [INN:BAN]
Oxiconazolum
Oxiconazol
(1Z)-N-[(2,4-Dichlorobenzyl)oxy]-1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanimine
MFCD00865580
Oxiconazole
Oxiconazol [INN-Spanish]
Oxiconazole (INN)
2',4'-Dichlor-O-(2,4-dichlorbenzyl)-2-(1-imidazolyl)-(Z)-acetophenonoxim
UNII-C668Q9I33J
1-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-yl)ethanone O-(2,4-dichlorobenzyl) oxime

Biological Activity

[Description]:

Oxiconazole (Ro 13-8996) is a broad spectrum anti-fungal agent which can inhibit the growth of Candida, Aspergillus and Trichophyton. Oxiconazole is also a highly efficacious activator of CYP3A4 transactivation, which could be antagonized by Rifampicin (HY-B0272) in a competitive manner. Oxiconazole exhibits inhibitory effect against colorectal cancer (CRC) via peroxiredoxin-2 (PRDX2)-mediated autophagy arrest[1][2][3].

[Related Catalog]:

Research Areas >> Cancer

Research Areas >> Infection

Signaling Pathways >> Metabolic Enzyme/Protease >> Cytochrome P450

Signaling Pathways >> Anti-infection >> Fungal

[Target]

CYP3A4

[In Vitro]

Oxiconazole (24 h; 0-40 μM) inhibits CRC cell growth[3]. Oxiconazole has antifungal activity against Candida, Aspergillus and Trichophyton[1]. Antifungal Activities of Oxiconazole[1]. Candida albicans Candida glabrata Candida parapsilosis Aspergillus fumigatus Aspergillus flavus Trichophyton mentagrophytes Trichophyton rubrum Oxiconazole 0.03 μg/mL 0.01 μg/mL 0.008 μg/mL 2 μg/mL 2 μg/mL 2 μg/mL 2 μg/mL Cell Proliferation Assay[3] Cell Line: HCT116, SW480, RKO, DLD-1, SW620, LoVo and NCM460 Concentration: 0-40 μM Incubation Time: 24 h Result: Exhibited inhibitory activity against HCT116, SW480, RKO, DLD-1, SW620, LoVo and NCM460 with IC50s of 25.86 μM, 27.34 μM, 21.01 μM, 25.56 μM, 21.75 μM, 24.87 μM and 126.4 μM.

[In Vivo]

Oxiconazole (50 mg/kg/day; IP; for 12 days) significantly restrains CRC cell growth[3]. Animal Model: BALB/c nude mice (injected subcutaneously with HCT116 cells (1×107/mouse)[3] Dosage: 50 mg/kg/day Administration: IP; for 12 days Result: Significantly restrained CRC cell growth and showed no obvious side effects.

[References]

[1]. Rossello A, et al. Synthesis, antifungal activity, and molecular modeling studies of new inverted oxime ethers of oxiconazole. J Med Chem. 2002 Oct 24;45(22):4903-12.

[2]. Svecova L, et al. Azole antimycotics differentially affect rifampicin-induced pregnane X receptor-mediated CYP3A4 gene expression. Drug Metab Dispos. 2008 Feb;36(2):339-48.

[3]. Shi J, et al. Repurposing Oxiconazole against Colorectal Cancer via PRDX2-mediated Autophagy Arrest. Int J Biol Sci. 2022 May 21;18(9):3747-3761.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
576.8±60.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₈H₁₃Cl₄N₃O

[ Molecular Weight ]:
429.127

[ Flash Point ]:
302.6±32.9 °C

[ Exact Mass ]:
426.981262

[ PSA ]:
39.41000

[ LogP ]:
5.83

[ Vapour Pressure ]:
0.0±1.5 mmHg at 25°C

[ Index of Refraction ]:
1.635

Safety Information

[ HS Code ]:
2933290090

Customs

[ HS Code ]: 2933290090

[ Summary ]:
2933290090. other compounds containing an unfused imidazole ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%