Miconazole
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Others |
| Catalog number | BBF-03854 |
| CAS | 22916-47-8 |
| Molecular Weight | 416.13 |
| Molecular Formula | C18H14Cl4N2O |
| Purity | >98% |
Online Inquiry
Description
Miconazole is an imidazole antifungal agent, developed by Janssen Pharmaceutica, commonly applied topically to the skin or to mucous membranes to cure fungal infections. It works by inhibiting the synthesis of ergosterol, a critical component of fungal cell membranes.
Specification
| Related CAS | 22832-87-7 (nitrate) |
| Synonyms | NSC 169434; NSC169434; NSC-169434; Daktarin IV |
| 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 |
| 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 |
Properties
| Appearance | White to Off-white Powder |
| Antibiotic Activity Spectrum | fungi |
| Boiling Point | 555.1°C at 760 mmHg |
| Melting Point | 159-163°C |
| Density | 1.4 g/cm3 |
| LogP | 6.1 |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | Miconazole interacts with 14-alpha 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 | LD50: 3800 mg/kg (Oral, Mouse); LD50: 3 gm/kg (Oral, Rat). |
Reference Reading
1. Synthesis and antimicrobial potential of nitrofuran–triazole congeners
Ahmed Kamal,* S. M. Ali Hussaini, M. Lakshmi Sucharitha. Org. Biomol. Chem.,2015, 13,9388–9397
Furthermore, these compounds were tested against the same fourteen fungal strains to evaluate their minimum fungicidal concentration (MFC) and the results are summarized in Table 4. Similarly, the results correlated well with the anti-fungal activity data and most of the compounds displayed MFC values identical to the standard miconazole. In particular, compound 9f showed MFC = 3.9 µg mL−1, compared to the standard (MFC = 7.8 µg mL−1) against C. parapsilosis MTCC 1744 and displayed the same efficacy as miconazole against several other tested fungal strains. On the whole, the results indicate that the compounds possess excellent antifungal potential, in some cases better than and/or equipotent to miconazole.
2. Discovery of new scaffolds from approved drugs as acetylcholinesterase inhibitors
Yao Chen, Xiaoli Xu, Tingming Fu, Wei Li, Zongliang Liu* and Haopeng Sun*. RSC Adv.,2015, 5,90288–90294
When Dyclonine and Miconazole were docked into the binding pocket of AChE, we observed different binding modes compared to the other four compounds mentioned above. Interestingly, the two compounds only located at the PAS of AChE. No group inserted into the CAS. This binding mode can support the non-competitive manner from kinetic study. We assumed that it was the length and themolecular shape of these two molecules caused such difference. Compared to the other four compounds, Dyclonine and Miconazole formed more shrink conformations, which made them could not cover the CAS and PAS simultaneously. Additionally, the two compounds were highly hydrophobic, containing multiple aromatic rings or alky chains. This made them were prone to the more hydrophobic PAS of AChE.
3. Structure of solid lipid nanoparticles produced by a microwave-assisted microemulsion technique
Rohan M. Shah,* Gary Bryant, Matthew Taylor, Daniel S. Eldridge, Enzo A. Palomboa and Ian H. Harding*. RSC Adv.,2016, 6,36803–36810
The difference in the release pattern is evident in Fig. 3 which is an overlay of release profiles of indomethacin and miconazole nitrate. This may be due to the difference in physicochemical properties of the drugs: indomethacin is weakly acidic (due to the presence of carboxylic acid functional groups) and has a low partition coefficient in octanol–water systems, with log P = 3.4;
miconazole nitrate is basic (due to the presence of imidazole ring) and has a high partition coefficient in octanol–water system, with log P = 6.3. These values suggest that miconazole nitrate has higher lipophilicity (and therefore, solubility in the lipid phase) than indomethacin. Thus, one interpretation of the release data is that indomethacin (low partition coefficient) is present predominantly in the shell (i.e. drug-enriched shell model) and released quickly. On the other hand, miconazole nitrate (high partition coefficient) should be solubilized in the molten lipid and crystallize within the lipid core (i.e. drug-enriched core model), thus providing a slower release. These findings support the hypothesis that indomethacin is primarily present in the shell and its release is diffusion-controlled. In contrast, the release of miconazole nitrate, which is predominantly present in the lipid core, is controlled by dissolution and diffusion.
Spectrum
LC-MS/MS Spectrum - LC-ESI-qTof , Positive
Experimental Conditions
Instrument Type: LC-ESI-qTof
Ionization Mode: Positive
Ionization Mode: Positive
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Mass Spectrum (Electron Ionization)
Recommended Products
| BBF-03754 | CASTANOSPERMINE | Inquiry |
| BBF-03753 | Baicalin | Inquiry |
| BBF-05862 | Epirubicin | Inquiry |
| BBF-00764 | Cerebroside C | Inquiry |
| BBF-02642 | Lactonamycin | Inquiry |
| BBF-01825 | Loganin | Inquiry |
Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
