Clotrimazole

Clotrimazole, sold under the brand name Lotrimin, among others, is an antifungal medication.[1] 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.[1] It can be taken by mouth or applied as a cream to the skin or in the vagina.[1]

Clotrimazole
Clinical data
Trade namesDesenex, CalmYourself, others
AHFS/Drugs.comMonograph
MedlinePlusa682753
Pregnancy
category
  • AU: A
  • C (by mouth) and B (topical) (US)
Routes of
administration
Topical, throat lozenge
ATC code
Legal status
Legal status
  • US: OTC (topical), ℞-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)
  • 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.[1] When applied to the skin, common side effects include redness and a burning sensation.[1] In pregnancy, use on the skin or in the vagina is believed to be safe.[1] There is no evidence of harm when used by mouth during pregnancy but this has been less well studied.[1] When used by mouth, greater care should be taken in those with liver problems.[1] It is in the azole class of medications and works by disrupting the fungal cell membrane.[1]

Clotrimazole was discovered in 1969.[2] It is on the World Health Organization's List of Essential Medicines.[3] It is available as a generic medication.[1]


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