Clotrimazole

Clotrimazole, sold under the brand name Lotrimin, among others, is an antifungal medication. It is used to treat vaginal yeast infections, oral thrush, diaper rash, tinea versicolor, and types of ringworm including athlete's foot and jock itch. It can be taken by mouth or applied as a cream to the skin or in the vagina.

Clotrimazole
Clinical data
Trade namesDesenex, CalmYourself, others
AHFS/Drugs.comMonograph
MedlinePlusa682753
Pregnancy
category
  • AU: A
Routes of
administration
Topical, throat lozenge
ATC code
Legal status
Legal status
  • US: OTC (topical), Rx-only (by mouth)
Pharmacokinetic data
BioavailabilityPoor absorption by mouth (lozenge), negligible absorption through intact skin (topical)
Protein binding90%
MetabolismLiver
Elimination half-life2 hours
Identifiers
  • 1-[(2-Chlorophenyl)(diphenyl)methyl]-1H-imidazole
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.041.589
Chemical and physical data
FormulaC22H17ClN2
Molar mass344.84 g·mol−1
3D model (JSmol)
Melting point147 to 149 °C (297 to 300 °F)
SMILES
  • Clc1ccccc1C(c2ccccc2)(c3ccccc3)n4ccnc4
  • InChI=1S/C22H17ClN2/c23-21-14-8-7-13-20(21)22(25-16-15-24-17-25,18-9-3-1-4-10-18)19-11-5-2-6-12-19/h1-17H Y
  • Key:VNFPBHJOKIVQEB-UHFFFAOYSA-N Y
  (verify)

Common side effects when taken by mouth include nausea and itchiness. When applied to the skin, common side effects include redness and a burning sensation. In pregnancy, use on the skin or in the vagina is believed to be safe. There is no evidence of harm when used by mouth during pregnancy but this has been less well studied. When used by mouth, greater care should be taken in those with liver problems. It is in the azole class of medications and works by disrupting the fungal cell membrane.

Clotrimazole was discovered in 1969. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication. In 2021, it was the 273rd most commonly prescribed medication in the United States, with more than 900,000 prescriptions.

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