Clotrimazole

Clotrimazole
Clinical data
Trade names	Desenex, CalmYourself, others
AHFS/Drugs.com	Monograph
MedlinePlus	a682753
Pregnancy; category	AU: A;
Routes of; administration	Topical, throat lozenge
ATC code	A01AB18 (WHO) D01AC01 (WHO) G01AF02 (WHO) QJ02AB90 (WHO);
Legal status
Legal status	CA: OTC; US: OTC (topical), Rx-only (by mouth);
Pharmacokinetic data
Bioavailability	Poor absorption by mouth (lozenge), negligible absorption through intact skin (topical)
Protein binding	90%
Metabolism	Liver
Elimination half-life	2 hours
Identifiers
	IUPAC name 1-[(2-Chlorophenyl)(diphenyl)methyl]-1H-imidazole;
CAS Number	23593-75-1 ;
PubChem CID	2812;
IUPHAR/BPS	2330;
DrugBank	DB00257 ;
ChemSpider	2710 ;
UNII	G07GZ97H65;
KEGG	D00282 ;
ChEBI	CHEBI:3764 ;
ChEMBL	ChEMBL104 ;
CompTox Dashboard (EPA)	DTXSID7029871 ;
ECHA InfoCard	100.041.589
Chemical and physical data
Formula	C22H17ClN2
Molar mass	344.84 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	147 to 149 °C (297 to 300 °F)
	SMILES Clc1ccccc1C(c2ccccc2)(c3ccccc3)n4ccnc4;
	InChI 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 ; Key:VNFPBHJOKIVQEB-UHFFFAOYSA-N ;
	(verify)

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 is in the azole class of medications and works by disrupting the fungal cell membrane. It can be taken by mouth or applied as a cream to the skin or in the vagina.

Common side effects of clotrimazole taken by mouth include nausea and itchiness. When it is applied to the skin, common side effects include redness and a burning sensation. In pregnancy, topical use, even in the vagina, is believed to be safe, nor is there evidence of harm by oral use, but the latter has been less well studied. Oral use requires greater care by those with liver ailments.

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.