Miconazole
White or off white powder
Others
Miconazole is an antifungal synthetic derivative of imidazole and used in the treatment of candidal skin infections, Miconazole selectively affects the integrity of fungal cell membranes, high in ergosterol content and different in composition from mammalian cells membranes. (NCI04)
Miconazole, also known as monistat or dactarin, belongs to the class of organic compounds known as benzylethers. These are aromatic ethers with the general formula ROCR' (R = alkyl, aryl; R'=benzene). Miconazole is a drug which is used for topical application in the treatment of tinea pedis (athlete’s foot), tinea cruris, and tinea corporis caused by trichophyton rubrum, trichophyton mentagrophytes, and epidermophyton floccosum, in the treatment of cutaneous candidiasis (moniliasis), and in the treatment of tinea versicolor. Miconazole exists as a solid and is considered to be practically insoluble (in water) and relatively neutral. Miconazole has been detected in multiple biofluids, such as urine and blood. Within the cell, miconazole is primarily located in the cytoplasm and membrane (predicted from logP). Miconazole is a potentially toxic compound.
Miconazole is a broad-spectrum azole antifungal with some activity against Gram-positive bacteria as well. It is widely used to treat mucosal yeast infections, including both oral and vaginal infections; although intravenous miconazole is no longer available, a wide variety of suppositories, creams, gels, and tablet-based products are available. Miconazole is thought to act primarily through the inhibition of fungal CYP450 14α-lanosterol demethylase activity. Miconazole was first synthesized in 1969 and first granted FDA approval on January 8, 1974, for sale by INSIGHT Pharmaceuticals as a topical cream. It is currently available as a variety of prescription and over the counter products. Despite having been in clinical use for an extended period, resistance to miconazole among susceptible organisms is relatively low. 416.1 g/mol
Miconazole, also known as monistat or dactarin, belongs to the class of organic compounds known as benzylethers. These are aromatic ethers with the general formula ROCR' (R = alkyl, aryl; R'=benzene). Miconazole is a drug which is used for topical application in the treatment of tinea pedis (athlete’s foot), tinea cruris, and tinea corporis caused by trichophyton rubrum, trichophyton mentagrophytes, and epidermophyton floccosum, in the treatment of cutaneous candidiasis (moniliasis), and in the treatment of tinea versicolor. Miconazole exists as a solid and is considered to be practically insoluble (in water) and relatively neutral. Miconazole has been detected in multiple biofluids, such as urine and blood. Within the cell, miconazole is primarily located in the cytoplasm and membrane (predicted from logP). Miconazole is a potentially toxic compound.
Miconazole is a broad-spectrum azole antifungal with some activity against Gram-positive bacteria as well. It is widely used to treat mucosal yeast infections, including both oral and vaginal infections; although intravenous miconazole is no longer available, a wide variety of suppositories, creams, gels, and tablet-based products are available. Miconazole is thought to act primarily through the inhibition of fungal CYP450 14α-lanosterol demethylase activity. Miconazole was first synthesized in 1969 and first granted FDA approval on January 8, 1974, for sale by INSIGHT Pharmaceuticals as a topical cream. It is currently available as a variety of prescription and over the counter products. Despite having been in clinical use for an extended period, resistance to miconazole among susceptible organisms is relatively low. 416.1 g/mol
Formulation:
416.1 g/mol
Source:
Usage:
Miconazole
The product is for non-human research only. Not for therapeutic or veterinary use.
Catalog Number: BT-276215
CAS Number: 22916-47-8
Molecular Formula: C18H14Cl4N2O
Molecular Weight: 416.1 g/mol
Purity: ≥ 98%
Inventory: In Stock
| Size | SKU | Price | |
|---|---|---|---|
| 1g | bt-276215-1g | $294.77 | |
| 5g | bt-276215-5g | $870.92 | |
| 25g | bt-276215-25g | $4,254.15 |
| CAS Number | 22916-47-8 |
|---|---|
| Product Name | Miconazole |
| Molecular Formula | C18H14Cl4N2O |
| Molecular Weight | 416.1 g/mol |
| Appearance | White or off white powder |
| InChI | 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 |
| InChI Key | BYBLEWFAAKGYCD-UHFFFAOYSA-N |
| IUPAC Name | 1-[2-(2,4-dichlorophenyl)-2-[(2,4-dichlorophenyl)methoxy]ethyl]imidazole |
| Canonical SMILES | C1=CC(=C(C=C1Cl)Cl)COC(CN2C=CN=C2)C3=C(C=C(C=C3)Cl)Cl |
| Description | Miconazole is an antifungal synthetic derivative of imidazole and used in the treatment of candidal skin infections, Miconazole selectively affects the integrity of fungal cell membranes, high in ergosterol content and different in composition from mammalian cells membranes. (NCI04) Miconazole, also known as monistat or dactarin, belongs to the class of organic compounds known as benzylethers. These are aromatic ethers with the general formula ROCR' (R = alkyl, aryl; R'=benzene). Miconazole is a drug which is used for topical application in the treatment of tinea pedis (athlete’s foot), tinea cruris, and tinea corporis caused by trichophyton rubrum, trichophyton mentagrophytes, and epidermophyton floccosum, in the treatment of cutaneous candidiasis (moniliasis), and in the treatment of tinea versicolor. Miconazole exists as a solid and is considered to be practically insoluble (in water) and relatively neutral. Miconazole has been detected in multiple biofluids, such as urine and blood. Within the cell, miconazole is primarily located in the cytoplasm and membrane (predicted from logP). Miconazole is a potentially toxic compound. Miconazole is a broad-spectrum azole antifungal with some activity against Gram-positive bacteria as well. It is widely used to treat mucosal yeast infections, including both oral and vaginal infections; although intravenous miconazole is no longer available, a wide variety of suppositories, creams, gels, and tablet-based products are available. Miconazole is thought to act primarily through the inhibition of fungal CYP450 14α-lanosterol demethylase activity. Miconazole was first synthesized in 1969 and first granted FDA approval on January 8, 1974, for sale by INSIGHT Pharmaceuticals as a topical cream. It is currently available as a variety of prescription and over the counter products. Despite having been in clinical use for an extended period, resistance to miconazole among susceptible organisms is relatively low. |
| Melting Point | 170 159-163°C |
| Other CAS Number | 22916-47-8 |
| Physical Description | Solid |
| Pictograms | Irritant;Environmental Hazard |
| Related CAS | 22832-87-7 (nitrate) |
| SMILES | C1=CC(=C(C=C1Cl)Cl)COC(CN2C=CN=C2)C3=C(C=C(C=C3)Cl)Cl |
| Solubility | 7.63e-04 g/L |
| Synonyms | Brentan Dactarin Miconasil Nitrate Miconazole Miconazole Nitrate Monistat Nitrate, Miconasil Nitrate, Miconazole R 14,889 R-14,889 R14,889 |
| Reference | 1: Lozano R, Frutos A. Time course of the drug-drug interaction of acenocoumarol-miconazole. Int J Clin Pharmacol Ther. 2017 Nov 22. doi: 10.5414/CP203090. [Epub ahead of print] PubMed PMID: 29162215. 2: Simmons KB, Kumar N, Plagianos M, Roberts K, Hoskin E, Han L, Alami M, Creasy G, Variano B, Merkatz R. Effects of concurrent vaginal miconazole treatment on the absorption and exposure of Nestorone® (segesterone acetate) and ethinyl estradiol delivered from a contraceptive vaginal ring: A randomized, crossover drug-drug interaction study. Contraception. 2017 Oct 30. pii: S0010-7824(17)30498-5. doi: 10.1016/j.contraception.2017.10.010. [Epub ahead of print] PubMed PMID: 29097225. 3: Kenechukwu FC, Attama AA, Ibezim EC, Nnamani PO, Umeyor CE, Uronnachi EM, Gugu TH, Momoh MA, Ofokansi KC, Akpa PA. Surface-modified mucoadhesive microgels as a controlled release system for miconazole nitrate to improve localized treatment of vulvovaginal candidiasis. Eur J Pharm Sci. 2018 Jan 1;111:358-375. doi: 10.1016/j.ejps.2017.10.002. Epub 2017 Oct 4. PubMed PMID: 28986195. 4: Ashtarinezhad A, Panahyab A, Mohamadzadehasl B, Shirazi FH. Characterization of Miconazole Effects on Mice Fetus Liver Tissue Using FTIR-MSP. Iran J Pharm Res. 2017 Spring;16(2):677-684. PubMed PMID: 28979322; PubMed Central PMCID: PMC5603877. 5: Gyanfosu L, Koffuor GA, Kyei S, Ababio-Danso B, Peprah-Donkor K, Nyansah WB, Asare F. Efficacy and safety of extemporaneously prepared miconazole eye drops in Candida albicans-induced keratomycosis. Int Ophthalmol. 2017 Sep 12. doi: 10.1007/s10792-017-0707-z. [Epub ahead of print] PubMed PMID: 28900810. 6: Kenechukwu FC, Attama AA, Ibezim EC. Novel solidified reverse micellar solution-based mucoadhesive nano lipid gels encapsulating miconazole nitrate-loaded nanoparticles for improved treatment of oropharyngeal candidiasis. J Microencapsul. 2017 Sep;34(6):592-609. doi: 10.1080/02652048.2017.1370029. Epub 2017 Sep 6. PubMed PMID: 28877639. 7: Pyo SM, Hespeler D, Keck CM, Müller RH. Dermal miconazole nitrate nanocrystals - formulation development, increased antifungal efficacy & skin penetration. Int J Pharm. 2017 Oct 5;531(1):350-359. doi: 10.1016/j.ijpharm.2017.08.108. Epub 2017 Sep 1. PubMed PMID: 28855137. 8: Du Y, Luo L, Sun S, Jiang Z, Guo X. Enantioselective separation and determination of miconazole in rat plasma by chiral LC-MS/MS: application in a stereoselective pharmacokinetic study. Anal Bioanal Chem. 2017 Nov;409(27):6315-6323. doi: 10.1007/s00216-017-0551-z. Epub 2017 Aug 29. PubMed PMID: 28852798. 9: Nave R, Klein S, Müller A, Chang X, Höchel J. Absence of Effect of Intravaginal Miconazole, Clindamycin, Nonoxynol-9, and Tampons on the Pharmacokinetics of an Anastrozole/Levonorgestrel Intravaginal Ring. J Clin Pharmacol. 2017 Aug 7. doi: 10.1002/jcph.984. [Epub ahead of print] PubMed PMID: 28783867. 10: Saboo S, Taylor LS. Water-induced phase separation of miconazole-poly (vinylpyrrolidone-co-vinyl acetate) amorphous solid dispersions: Insights with confocal fluorescence microscopy. Int J Pharm. 2017 Aug 30;529(1-2):654-666. doi: 10.1016/j.ijpharm.2017.07.034. Epub 2017 Jul 11. PubMed PMID: 28705623. |
| PubChem Compound | Miconazole |
| Last Modified | Mar 14 2022 |