Oxyconazole (24 hours; 0-40 μM) suppresses the development of CRC cells [3]. Trichophyton, Aspergillus, and Candida are susceptible to the antifungal effects of oxyconazole [1]. Oxyconazole's antifungal activity [1]. Candida albicans Candida pneumonia Porphyromonas fumigatus Aspergillus flavus Mentagrophytes Trichophyton Rubrum Trichophyton oxyconazole A 0.03 μg/mL, a 0.01 μg/mL, and a 0.008 μg/mL, two μg/mL, two μg/mL, and two μg/mL

For 12 days, oxyconazole (50 mg/kg/day; IP) dramatically reduces the development of colorectal cancer cells [3].

Cell Proliferation Assay[3]
Cell Types: HCT116, SW480, RKO, DLD-1, SW620, LoVo and NCM460
Tested Concentrations: 0-40 μM
Incubation Duration: 24 hrs (hours)
Experimental Results: For HCT116, SW480, RKO, DLD -1, SW620, LoVo and NCM460 demonstrated inhibitory activity IC50 of 25.86 μM, 27.34 μM, 21.01 μM, 25.56 μM, 21.75 μM, 24.87 μM and 126.4 μM.

Animal/Disease Models: BALB/c nude mice (subcutaneous injection of HCT116 cells (1×107/mouse) [3]
Doses: 50 mg/kg/day
Route of Administration: IP; 12 days.
Experimental Results: Dramatically inhibited CRC cell growth, and No obvious side effects.

Absorption, Distribution and Excretion
Systemic absorption of oxiconazole is low.

Effects During Pregnancy and Lactation
◉ Summary of Use during Lactation
Topical oxiconazole has not been studied during breastfeeding. Because less than 1% is absorbed after topical application, it is considered a low risk to the nursing infant.[1] Avoid application to the nipple area and ensure that the infant's skin does not come into direct contact with the areas of skin that have been treated. Only water-miscible cream or gel products should be applied to the breast because ointments may expose the infant to high levels of mineral paraffins via licking.[2]
◉ Effects in Breastfed Infants
Relevant published information was not found as of the revision date.
◉ Effects on Lactation and Breastmilk
Relevant published information was not found as of the revision date.

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

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

Oxiconazole is 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. It has a role as an antiinfective agent. It is a member of imidazoles, an oxime O-ether, a dichlorobenzene, an imidazole antifungal drug and a conazole antifungal drug. It is a conjugate base of an oxiconazole(1+).
Oxiconazole is an antifungal agent that is commonly found in topical formulations. It is marketed under the brand names Oxistat and Oxistat, and is used in the treatment of various skin infections such as athlete's foot, jock itch and ringworm.
Oxiconazole is an Azole Antifungal.
Oxiconazole is a broad spectrum imidazole derivative with antifungal activity. Although the exact mechanism of action has yet to be fully elucidated, oxiconazole, like other azole antifungals, most likely inhibits the cytochrome P450-dependent demethylation of lanosterol. This prevents the synthesis of ergosterol which is a crucial component of fungal cell membrane. By disrupting fungal cell membrane synthesis and integrity, oxiconazole alters fungal cell membrane permeability, promotes loss of essential intracellular components and eventually inhibits fungal cell growth.
See also: Oxiconazole Nitrate (has salt form).

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Drug Indication
For treatment of dermal fungal infection.
FDA Label

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Mechanism of Action
Oxiconazole inhibits ergosterol biosynthesis, which is required for cytoplasmic membrane integrity of fungi. It acts to destabilize the fungal cyctochrome P450 51 enzyme (also known as Lanosterol 14-alpha demethylase). This is vital in the cell membrance structure of the fungus. Its inhibition leads to cell lysis. Oxiconazole has also been shown in inhibit DNA synthesis and suppress intracellular concentrations of ATP. Like other imidazole antifungals, Oxiconazole can increase membrane permeability to zinc, augmenting its cytotoxicity.

C18H13CL4N3O

429.12

426.981

64211-45-6

Oxiconazole nitrate;64211-46-7

5353853

Typically exists as solid at room temperature

1.4±0.1 g/cm3

576.8±60.0 °C at 760 mmHg

302.6±32.9 °C

0.0±1.5 mmHg at 25°C

1.635

5.83

0

3

6

26

481

0

C1=CC(=CC(=C1CO/N=C(\CN2C=CN=C2)/C3=C(C=C(C=C3)Cl)Cl)Cl)Cl

WVNOAGNOIPTWPT-NDUABGMUSA-N

InChI=1S/C18H13Cl4N3O.HNO3/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;2-1(3)4/h1-8,11H,9-10H2;(H,2,3,4)/b24-18+;

(Z)-1-(2,4-dichlorophenyl)-N-[(2,4-dichlorophenyl)methoxy]-2-imidazol-1-ylethanimine;nitric acid

Ro 13-8996 Oxiconazolum Oxiconazole

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

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Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).

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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)

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Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).

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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders

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Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

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 (Please use freshly prepared in vivo formulations for optimal results.)