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| Targets |
Miconazole targets lanosterol demethylase, a key enzyme in the ergosterol biosynthesis pathway. By inhibiting lanosterol demethylase, miconazole blocks the synthesis of ergosterol, an essential component of fungal cell membranes. This inhibition disrupts the substance transportation and permeability barrier of the cell membrane, leading to fungal cell death. The antimicrobial activity is induced by inhibiting ergosterol synthesis to inhibit the substance transportation and permeability barrier of the cell membrane. Miconazole also induces the formation of reactive oxygen species, which contributes to its antifungal activity. The compound's broad-spectrum activity against various fungi, including Trichophyton, Microsporum, and Candida albicans, is mediated through this mechanism. Miconazole also has some activity against Gram-positive bacteria. In addition to its antifungal effects, miconazole enhances the generation of mature oligodendrocytes from progenitor cells.
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| ln Vitro |
Developed by Janssen Pharmaceutica, miconazole nitrate (R18134 nitrate) is an imidazole antifungal that is usually administered topically to the skin or mucous membranes to treat fungal infections. By preventing the creation of ergosterol, a crucial part of fungal cell membranes, it puts you to sleep. Some species of Leishmania, a single-celled parasite with ergocystis in its cell membrane, use it. It has some antibacterial qualities in addition to antifungal and antiparasitic ones. In Ektachrome films, formaldehyde is substituted by miconazole nitrate (R18134 Nitrate) in the last rinse of the Kodak E-6 process and comparable Fuji CR-56 procedures. As a final rinse ingredient, Fuji Hunt incorporates miconazole into their C-41RA Quick Access Color Negative Process formulation. from the Wikipedia.
In vitro, miconazole nitrate demonstrates potent antifungal activity against a wide range of fungi. The compound inhibits lanosterol demethylase and induces the formation of reactive oxygen species. It exhibits strong antimicrobial activity against various fungi such as Trichophyton, Microsporum, and Candida albicans. The antimicrobial activity is induced by inhibiting ergosterol synthesis. Miconazole nitrate also has some activity against Gram-positive bacteria. In addition to its antifungal effects, miconazole enhances the generation of mature oligodendrocytes from progenitor cells in vitro. The compound promotes the differentiation of mature oligodendrocytes from progenitor cells. Miconazole's in vitro activity against various fungal pathogens makes it a valuable antifungal agent for topical and systemic use. |
| ln Vivo |
In vivo, miconazole nitrate demonstrates efficacy in treating various fungal infections. The compound is widely used to treat mucosal yeast infections, including both oral and vaginal infections. Miconazole nitrate is a gold-standard agent in treating vaginal yeast infections (candidiasis) and oral thrush, conditions primarily caused by Candida species. It is commonly used as a topical drug for skin infections, including athlete's foot, ringworm, and yeast infections. Topical antifungals are usually effective for the treatment of uncomplicated tinea corporis or tinea cruris. Miconazole promotes myelination in vivo. Intravenous miconazole is no longer available. The compound's efficacy in treating various fungal infections has been well-established through clinical use.
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| Enzyme Assay |
In vitro enzyme assays for miconazole typically measure lanosterol demethylase inhibition. The enzyme is incubated with miconazole at various concentrations and a substrate such as lanosterol. The production of demethylated products is measured by HPLC or other analytical methods. The IC₅₀ is calculated from the dose-response curve. For studies investigating the compound's effects on ergosterol biosynthesis, fungal cells are treated with miconazole, and ergosterol content is measured by HPLC or spectrophotometry. For studies investigating the compound's effects on reactive oxygen species formation, cells are treated with miconazole, and ROS levels are measured using fluorescent dyes such as DCFH-DA. The compound's antifungal activity can be assessed using standard susceptibility testing methods such as broth microdilution.
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| Cell Assay |
Cellular assays for miconazole typically employ fungal cell lines or primary fungal cultures to evaluate the compound's antifungal activity. Fungi such as Candida albicans, Trichophyton, or Microsporum are cultured in appropriate media and treated with miconazole at various concentrations. Fungal growth is assessed by measuring optical density or by colony counting. The minimum inhibitory concentration (MIC) is determined. For studies investigating the mechanism of action, fungal cells are treated with miconazole, and ergosterol content or reactive oxygen species levels are measured. For studies investigating the compound's effects on mammalian cells, oligodendrocyte progenitor cells are treated with miconazole, and differentiation and myelination are assessed. Cell viability is assessed using standard assays such as MTT or resazurin reduction.
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| Animal Protocol |
In vivo animal experiments for miconazole employ various models of fungal infection. For studies investigating the treatment of vaginal candidiasis, animal models of vaginal infection are used, and miconazole is administered topically or intravaginally. Fungal burden is assessed by culturing vaginal swabs. For studies investigating the treatment of dermatophytosis, animal models of skin infection are used, and miconazole is applied topically. Lesion size and fungal burden are assessed. For studies investigating the compound's effects on myelination, animal models are used, and miconazole is administered, and myelination is assessed histologically. For toxicology studies, animals are administered miconazole at various doses, and adverse effects are assessed. Dosing regimens vary depending on the experimental objectives and route of administration.
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| ADME/Pharmacokinetics |
The pharmacokinetic properties of miconazole nitrate are characterized by limited systemic absorption following topical or intravaginal administration. Miconazole persists in the vagina for up to 72 hours after a single dose. Systemic absorption of miconazole after intravaginal administration is limited, with a bioavailability of 1-2% following intravaginal administration of a 1.2 g dose. Miconazole remains in the skin after topical application for up to 4 days. Systemic absorption of miconazole is limited, with a bioavailability of less than 1% following topical application. Absorbed miconazole is bound to plasma proteins (88.2%) and red blood cells (10.6%). Plasma concentrations of miconazole were not quantifiable (≤0.5 ng/mL) in the majority of infants treated with multiple daily applications.
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| Toxicity/Toxicokinetics |
The toxicity profile of miconazole nitrate is favorable for topical use. The compound is generally well-tolerated when applied topically or intravaginally. Common adverse effects include local irritation, burning, or itching at the application site. Systemic toxicity is rare due to the limited systemic absorption of the compound. Miconazole nitrate is not recommended for use in patients with known hypersensitivity to imidazole antifungals. The compound's safety in pregnancy has been studied, and it is generally considered safe for topical use during pregnancy when indicated. However, intravenous miconazole is no longer available due to safety concerns. The compound's potential for drug interactions is limited due to its low systemic absorption.
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| References | |
| Additional Infomation |
Miconazole is a prescription antifungal medication approved by the U.S. Food and Drug Administration (FDA) for the treatment of mucocutaneous candidiasis, including: Oropharyngeal candidiasis, a fungal infection of the posterior pharynx; and vulvovaginal candidiasis. Oropharyngeal and vulvovaginal candidiasis may be opportunistic infections (OIs) of HIV. Miconazole nitrate is the nitrate form of miconazole, a synthetic imidazole antifungal derivative used to treat Candida skin infections. Miconazole selectively disrupts the integrity of the fungal cell membrane, which is rich in ergosterol and has a composition different from mammalian cell membranes. (NCI04) An imidazole antifungal medication, available for topical application or intravenous infusion. See also: Miconazole (active ingredient); Miconazole nitrate; Vaseline; Zinc oxide (ingredient); Miconazole nitrate; Vaseline; Zinc oxide (ingredient)... See more...
Miconazole nitrate is a broad-spectrum azole antifungal agent that blocks ergosterol biosynthesis. It inhibits lanosterol demethylase and induces the formation of reactive oxygen species. Miconazole nitrate is a gold-standard agent in treating vaginal yeast infections and oral thrush. It exhibits strong antimicrobial activity against various fungi such as Trichophyton, Microsporum, and Candida albicans. The compound also has some activity against Gram-positive bacteria. Miconazole enhances the generation of mature oligodendrocytes from progenitor cells in vitro and promotes myelination in vivo. It is commonly used as a topical drug for skin infections. Intravenous miconazole is no longer available. Systemic absorption of miconazole is limited following topical or intravaginal administration. |
| Molecular Formula |
C18H15CL4N3O4
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|---|---|
| Molecular Weight |
479.13
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| Exact Mass |
476.981
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| CAS # |
22832-87-7
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| Related CAS # |
Miconazole;22916-47-8;Miconazole-d5 nitrate (2,4-Dichlorobenzyloxy-d5);1398065-80-9
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| PubChem CID |
68553
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| Appearance |
White to off-white solid powder
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| Density |
1.451g/cm3
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| Boiling Point |
555.1ºC at 760 mmHg
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| Melting Point |
170-185ºC
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| Flash Point |
289.5ºC
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| LogP |
6.63
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
29
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| Complexity |
441
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
MCCACAIVAXEFAL-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C18H14Cl4N2O.HNO3/c19-13-2-1-12(16(21)7-13)10-25-18(9-24-6-5-23-11-24)15-4-3-14(20)8-17(15)222-1(3)4/h1-8,11,18H,9-10H2(H,2,3,4)
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| Chemical Name |
1-(2-((2,4-dichlorobenzyl)oxy)-2-(2,4-dichlorophenyl)ethyl)-1H-imidazole nitrate
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| Synonyms |
Andergin Deralbine Florid Micatin R 14889 R14889 R-14889
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~50 mg/mL (~104.35 mM)
H2O : ~0.1 mg/mL (~0.21 mM) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.22 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (5.22 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. 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. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (5.22 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.0871 mL | 10.4356 mL | 20.8712 mL | |
| 5 mM | 0.4174 mL | 2.0871 mL | 4.1742 mL | |
| 10 mM | 0.2087 mL | 1.0436 mL | 2.0871 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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