Clotrimazole (brand name Canesten or Lotrimin) is an antifungal medication commonly used in the treatment of fungal infections (of both humans and other animals) such as vaginal yeast infections, oral thrush, and ringworm. It is also used to treat athlete's foot and jock itch.
Medical uses [edit]
It is commonly available as an over-the-counter substance in various dosage forms, such as a cream, and also (especially in the case of ear infection) as a combination medicine. It is also available as a troche or throat lozenge (prescription only). For ear infection, it is often applied in liquid form, as ear drops. Fungal infections can be slow to clear up compared to bacterial infections, so the usual course for an antifungal agent is, in general, longer than the typical three to seven days of an antibiotic.
Clotrimazole is also commonly used in conjunction with betamethasone. Additionally, clotrimazole is used to treat the sickling of cells (related to sickle cell anemia) by blocking ion channels or clocip B channels in the red blood cell membrane, keeping ions and water within the cell.[1][2]
Mechanism of action [edit]
The primary mechanism of action of clotrimazole is against the division and growing of fungi.[3] Clotrimazole alters the permeability of the fungal cell wall and inhibits the activity of enzymes within the cell. It specifically inhibits the biosynthesis of ergosterol and other sterols required for cell membrane production. Studies show minimal concentrations of clotrimazole cause leakage of intracellular phosphorus compounds into the ambient medium, along with the breakdown of cellular nucleic acids and an accelerated K+ efflux.[3] This leads eventually to the cell's death. It does not appreciably spread through the user's body, but remains at the point of application.[4]
Drug interactions [edit]
Potential for drug interactions with clotrimazole oral exists, as it is a potent, specific inhibitor of cytochrome P450 oxidase and may alter the metabolism of other drugs.
Side effects [edit]
Side effects include skin rash, hives, blistering, burning, itching, peeling, redness, stinging, swelling, or other sign of skin irritation.[5]
Production [edit]
This compound (3) is produced by alkylating imidazole (1) with o-chlorotrityl chloride (2) in acetone, with triethylamine as the base.[6]
Environmental impact [edit]
Some research suggests clotrimazole, in combination with other commonly used chemicals, has negative effects on the ocean environment, in particular on microalgae.[7]
References [edit]
External links [edit]
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