Miconazole
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| Systematic (IUPAC) name | |
|---|---|
| 1-(2-(2,4-Dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl)-1H-imidazole | |
| Identifiers | |
| CAS number | 22916-47-8 |
| ATC code | D01AC02 A01 A07 G01 |
| PubChem | 4189 |
| DrugBank | APRD01115 |
| ChemSpider | 4044 |
| Chemical data | |
| Formula | C18H14Cl4N2O |
| Mol. mass | 416.127 g/mol |
| Pharmacokinetic data | |
| Bioavailability | n/a |
| Metabolism | n/a |
| Half life | n/a |
| Excretion | n/a |
| Therapeutic considerations | |
| Pregnancy cat. |
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| Legal status | |
| Routes | topical, vaginal |
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Miconazole is an imidazole antifungal agent, developed by Janssen Pharmaceutica, and commonly applied topically (to the skin) or mucus membranes to cure fungal infections. It works by inhibiting the synthesis of ergosterol, a critical component of fungal cell membranes. It can also be used against certain species of Leishmania protozoa (which are a type of unicellular parasite), as these also contain ergosterol in their cell membranes. In addition to its antifungal and antiparasitic actions, it also has some limited antibacterial properties. It is marketed in various formulations under various brand names (see below).
Miconazole is also used in Ektachrome film developing (along with surfactants such as Photo-Flo) in the final rinse of the Kodak E-6 process and similar Fuji CR-56 process, replacing formaldehyde. Fuji Hunt also includes miconazole as a final rinse additive in their formulation of the process C-41RA rapid access color negative developing process.
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[edit] Indications
Miconazole is mainly used externally for the treatment of athlete's foot, ringworm and jock itch. Internal application is used for oral or vaginal thrush (yeast infection). In addition the oral gel may also be used for the lip disorder angular cheilitis.
It has an advantage over nystatin in the treatment of neonatal oral thrush in that the latter is only licensed in the UK for those over the age of one month; but note the possibility for drug interactions.
[edit] Side effects
Unlike nystatin, some miconazole is absorbed by the intestinal tract when used orally (and possibly if used vaginally[1]) which may lead to drug interactions.
Of note may be interactions with anticoagulants, phenytoin, terbinafine, some newer atypical antipsychotics, ciclosporin and some statins used to treat hypercholesterolemia.
[edit] Brand names and formulations
Oral treatment: (brands: Daktarin in UK)
- Oral gel 24 mg/ml (20 mg/g)
External skin treatment: (brands: Desenex in US and Canada (not to be confused with Tussionex, Micatin, Monistat-Derm, Daktarin in UK, Australia and Belgium, Decocort in Malaysia)
- Topical cream: 2%.
- Combination: 2% cream with 1% hydrocortisone (Daktacort in UK, Daktodor in Greece)
Vaginal treatment: (brands: Miconazex, Monistat, Femizol or Gyno-Daktariin in UK)
- Pessaries: 200 mg or 100 mg
- Vaginal cream: 2%
- Combination: 2% cream with either 100 mg or 200 mg..
[edit] Physical properties
The solubilities of miconazole nitrate powder are 0.03% in water, 0.76% in ethanol and up to 4% in acetic acid.[2]
[edit] See also
[edit] References
- ^ British National Formulary '45' March 2003
- ^ United States Patent 5461068
[edit] External links
[edit] Medical
- Micatin
- Miconazole (www.meds-help.com)
- Miconazole (National Institutes of Health)
- United States Patent 5461068 Imidazole derivative tincture and method of manufacture
[edit] Photographic
- Kodak process E6 Ektachrome (color transparency) processing manual Z-119
- Kodak process E6 Q-LAB processing manual Z-6 (more details than processing manual Z119 above)
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