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| ln Vitro |
Miconazole is a topical imidazole antifungal medication that was created by Janssen Pharmaceutica to treat fungal infections of the skin or mucous membranes. Ergosterol is a crucial component of fungal cell membranes, and it functions by preventing its formation. Additionally, it is utilized to combat some species of Leishmania, a single-celled parasite whose cell membrane also contains ergosterol. It also possesses certain antibacterial qualities in addition to its antifungal and antiparasitic actions. Miconazole is also utilized as a formaldehyde substitute in the development of Ektachrome film during the Kodak E-6 process' final processing, as well as in the comparable Fuji CR-56 process. In the composition of its C-41RA Quick Access color negative developing process, Fuji Hunt also incorporates Miconazole as a final rinse ingredient.
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| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion
Miconazole given to healthy volunteers as a single 50 mg oral tablet produced a mean Cmax of 15.1 ± 16.2 mcg/mL, a mean AUC0-24 of 55.2 ± 35.1 mcg\*h/mL, and a median Tmax of 7 hours (range 2.0-24.1). In these patients measurable plasma concentrations ranged from 0.5 to 0.83 mcg/mL. Topical miconazole is absorbed poorly into the systemic circulation. In pediatric patients aged 1-21 months given multiple topical applications of miconazole ointment for seven days, the plasma miconazole concentration was less than 0.5 ng/mL in 88% of the patients, with the remaining patients having a concentration of 0.57 and 0.58 ng/mL, respectively. Similarly, patients. administered with a vaginal 1200 mg ovule had a mean Cmax of 10.71 ng/mL, mean Tmax of 18.4 hours, and mean AUC0-96 of 477.3 ng\*h/mL. Miconazole is excreted through both urine and feces; less than 1% of unchanged miconazole is recovered in urine. A 1200 mg miconazole vaginal suppository resulted in a calculated apparent volume of distribution of 95 546 L while a 100 mg vaginal cream yielded an apparent volume of distribution of 10 911L. Metabolism / Metabolites Miconazole is metabolized in the liver and does not give rise to any active metabolites. Biological Half-Life Miconazole has a terminal half-life of 24 hours. |
| Toxicity/Toxicokinetics |
Toxicity Summary
Miconazole interacts with 14-α demethylase, a cytochrome P-450 enzyme necessary to convert lanosterol to ergosterol. As ergosterol is an essential component of the fungal cell membrane, inhibition of its synthesis results in increased cellular permeability causing leakage of cellular contents. Miconazole may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms, inhibit purine uptake, and impair triglyceride and/or phospholipid biosynthesis. Toxicity Data LD50: 3800 mg/kg (Oral, Mouse) (A308) LD50: 3 gm/kg (Oral, Rat) (A308) |
| References | |
| Additional Infomation |
Pharmacodynamics
Miconazole is an azole antifungal that functions primarily through inhibition of a specific demethylase within the CYP450 complex. As miconazole is typically applied topically and is minimally absorbed into the systemic circulation following application, the majority of patient reactions are limited to hypersensitivity and cases of anaphylaxis. Patients using intravaginal miconazole products are advised not to rely on contraceptives to prevent pregnancy and sexually transmitted infections, as well as not to use tampons concurrently. |
| Molecular Formula |
C18H14CL4N2O
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| Molecular Weight |
416.13
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| Exact Mass |
413.986
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| CAS # |
22916-47-8
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| Related CAS # |
Miconazole nitrate;22832-87-7;Miconazole-d5;1216653-50-7;Miconazole-d5 nitrate;1216653-51-8;Miconazole-d2;2140316-33-0
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| PubChem CID |
4189
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| Appearance |
White to off-white solid powder
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| Density |
1.4±0.1 g/cm3
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| Boiling Point |
555.1±50.0 °C at 760 mmHg
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| Melting Point |
159-163ºC
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| Flash Point |
289.5±30.1 °C
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| Vapour Pressure |
0.0±1.4 mmHg at 25°C
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| Index of Refraction |
1.625
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| LogP |
5.93
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
25
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| Complexity |
417
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
BYBLEWFAAKGYCD-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C18H14Cl4N2O/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)22/h1-8,11,18H,9-10H2
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| Chemical Name |
1-[2-(2,4-dichlorophenyl)-2-[(2,4-dichlorophenyl)methoxy]ethyl]imidazole
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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 |
| 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 : 100 mg/mL (240.31 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.01 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: 2.08 mg/mL (5.00 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 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: ≥ 2.08 mg/mL (5.00 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 | 2.4031 mL | 12.0155 mL | 24.0310 mL | |
| 5 mM | 0.4806 mL | 2.4031 mL | 4.8062 mL | |
| 10 mM | 0.2403 mL | 1.2015 mL | 2.4031 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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