ethanone, 1-[4-[4-[[(2S,4R)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]-
Ketoconazole, is an antifungal medication used to treat a number of fungal infections.[8] Applied to the skin it is used for fungal skin infections such as tinea, cutaneous candidiasis, pityriasis versicolor, dandruff, and seborrheic dermatitis.[9] Taken by mouth it is a less preferred option and only recommended for severe infections when other agents cannot be used.[8] Other uses include in the treatment of excessive hair growth and Cushing's syndrome.[8]
Common side effects when applied to the skin include redness.[9] Common side effects when taken by mouth include nausea, headache, and liver problems.[8] Liver problems may result in death or the need for a liver transplantation.[8][10] Other severe side effect when taken by mouth include QT prolongation, adrenocortical insufficiency, and anaphylaxis.[8][10] It is an imidazole and works by affecting the production of ergosterol required for the fungal cell membrane thereby slowing growth.[8]
Ketoconazole was patented in 1977 and came into medical use in 1981.[11] It is available as a generic medication and formulations that are applied to the skin are over the counter in the United Kingdom.[9] In 2017, it was the 219th most commonly prescribed medication in the United States, with more than two million prescriptions.[12][13] The formulation that is taken by mouth was withdrawn in the European Union and in Australia in 2013[14][15] and in China in 2015.[16] In addition, its use was restricted in the United States and Canada in 2013.[15]