Miconazole

Miconazole
ATC Code A01AB09, A07AC01, D01AC02, G01AF04, J02AB01, S02AA13
Formula C18H14Cl4N2O
Molar Mass (g·mol−1) 416,13
Physical State solid
Melting Point (°C) 83–87
PKS Value 6,91
CAS Number 22916-47-8
PUB Number 4189
Drugbank ID DB01110
Solubility sparingly soluble in water

Basics

Miconazole is an antifungal used to treat ringworm, pityriasis versicolor, and yeast infections of the skin or vagina. It is used for ringworms on the body, groin, and feet (athlete's foot). It is applied as a cream or ointment to the skin or vagina.

Pharmacology

Pharmacodynamics

Miconazole inhibits the enzyme 14α-sterol demethylase found exclusively in fungi, resulting in decreased production of ergosterol. Ergosterol is an important component of the mycotic cell wall. Thus, inhibition of ergosterol synthesis leads to dissolution fungal cells. In addition to its antifungal effects, miconazole, like ketoconazole, is known to be an antagonist of the glucocorticoid receptor.

Pharmacokinetics

After application to the skin, miconazole can be detected in the skin for up to four days. Less than 1% is absorbed into the bloodstream, where 88.2% is bound to plasma proteins and 10.6% to blood cells. The substance is partially metabolized and excreted mainly in the faeces.

Toxicity

Side effects

Side effects are very unlikely as the drug is only absorbed to a very small extent and does not normally interact with human cells.

Interactions
Wechselwirkungen sind möglich mit Antikoagulantien, Phenytoin, Terbinafin, einige neuere atypische Antipsychotika, Cyclosporin und einige Statine zur Behandlung von Hypercholesterinämie.

Toxicological data

LD50 (rat, oral): 550 mg-kg-1

Sources

  • Drugbank
  • PubChem
  • Aktories, Förstermann, Hofmann, Starke: Allgemeine und spezielle Pharmakologie und Toxikologie, Elsvier, 2017
Markus Falkenstätter

Markus Falkenstätter
Author

Markus Falkenstätter ist Autor zu pharmazeutischen Themen in der Medizin-Redaktion von Medikamio. Er befindet sich im letzten Semester seines Pharmaziestudiums an der Universität Wien und liebt das wissenschaftliche Arbeiten im Bereich der Naturwissenschaften.

Mag. pharm Stefanie Lehenauer

Mag. pharm Stefanie Lehenauer
Lector

Stefanie Lehenauer ist seit 2020 freie Autorin bei Medikamio und studierte Pharmazie an der Universität Wien. Sie arbeitet als Apothekerin in Wien und ihre Leidenschaft sind pflanzliche Arzneimittel und deren Wirkung.

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