| Systematic (IUPAC) name | |
|---|---|
| 1-[(2-chlorophenyl)(diphenyl)methyl]-1H-imidazole | |
| Clinical data | |
| Trade names | Lotrimin AF, Mycelex |
| AHFS/Drugs.com | monograph |
| MedlinePlus | a682753 |
| Pregnancy cat. | A(AU) C (oral) & B (topical) (US) |
| Legal status | P (UK) |
| Routes | topical |
| Pharmacokinetic data | |
| Bioavailability | Poorly and erratically absorbed orally |
| Protein binding | 90% |
| Metabolism | hepatic |
| Half-life | 2 hours |
| Identifiers | |
| CAS number | 23593-75-1 |
| ATC code | A01AB18 D01AC01 G01AF02 QJ02AB90 |
| PubChem | CID 2812 |
| DrugBank | APRD00244 |
| ChemSpider | 2710 |
| UNII | G07GZ97H65 |
| KEGG | D00282 |
| ChEBI | CHEBI:3764 |
| ChEMBL | CHEMBL104 |
| Chemical data | |
| Formula | C22H17ClN2 |
| Mol. mass | 344.837 g/mol |
| SMILES | eMolecules & PubChem |
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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.
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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 (prescription only). For ear infection, it is often applied in liquid form, as ear drops. Fungal infections can be slow to clear up, so the usual course for an anti-fungal agent is, in general, longer than the typical 3–7 days of an antibiotic. Clotrimazole is also commonly found in conjunction with Betamethasone, known as Lotriderm, to add steroid properties. Additionally, Clotrimazole is used to treat the sickling of cells (related to sickle cell anemia) by blocking ion channels in the RBC (red blood cell) membrane, keeping ions and water within the cell.[1][2]
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. Studies show that minimal concentrations of clotrimazole causes 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]
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 include skin rash, hives, blistering, burning, itching, peeling, redness, stinging, swelling, or other sign of skin irritation.[5]
This compound (3) is produced by alkylating imidazole (1) with o-chlorotrityl chloride (2) in acetone, with triethylamine as the base.[6]
Some research suggests that, in combination with other commonly used chemicals, clotrimazole has negative effects on the ocean environment, in particular microalgae.[7]
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