Clotrimazole

Not to be confused with Clomethiazole, Chlormidazole, or Co-trimoxazole.

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
  • CA: OTC[1]
  • 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 Edit this at Wikidata
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 checkY
  • Key:VNFPBHJOKIVQEB-UHFFFAOYSA-N checkY
  (verify)

Clotrimazole, sold under the brand name Lotrimin, among others, is an antifungal medication.[2] 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.[2] It can be taken by mouth or applied as a cream to the skin or in the vagina.[2]

Common side effects when taken by mouth include nausea and itchiness.[2] When applied to the skin, common side effects include redness and a burning sensation.[2] In pregnancy, use on the skin or in the vagina is believed to be safe.[2] There is no evidence of harm when used by mouth during pregnancy but this has been less well studied.[2] When used by mouth, greater care should be taken in those with liver problems.[2] It is in the azole class of medications and works by disrupting the fungal cell membrane.[2]

Clotrimazole was discovered in 1969.[3] It is on the World Health Organization's List of Essential Medicines.[4] It is available as a generic medication.[2] In 2021, it was the 273rd most commonly prescribed medication in the United States, with more than 900,000 prescriptions.[5][6]

  1. ^ "Product monograph brand safety updates". Health Canada. 6 June 2024. Retrieved 8 June 2024.
  2. ^ a b c d e f g h i j American Society of Health-System Pharmacists (8 February 2016). "Clotrimazole Monograph for Professionals". www.drugs.com. Archived from the original on 28 October 2016. Retrieved 28 October 2016.
  3. ^ Walker SR (2012). Trends and Changes in Drug Research and Development. Springer Science & Business Media. p. 109. ISBN 9789400926592. Archived from the original on 14 September 2016.
  4. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  5. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  6. ^ "Clotrimazole - Drug Usage Statistics". ClinCalc. Archived from the original on 18 January 2024. Retrieved 14 January 2024.