Clotrimazole

Clotrimazole

Clinical data
Trade names	Desenex, Canesten, others
AHFS/Drugs.com	Monograph
MedlinePlus	a682753
Pregnancy category	AU: A C (by mouth) and B (topical) (US)
Routes of administration	Topical, throat lozenge
ATC code	A01AB18 (WHO) D01AC01 (WHO) G01AF02 (WHO) QJ02AB90 (WHO)
Legal status
Legal status	US: OTC (topical), ℞-only (by mouth)
Pharmacokinetic data
Bioavailability	Poor absorption by mouth (lozenge), negligible absorption through intact skin (topical)
Protein binding	90%
Metabolism	Liver
Biological half-life	2 hours
Identifiers
IUPAC name 1-[(2-Chlorophenyl)(diphenyl)methyl]-1H-imidazole
CAS Number	23593-75-1 Y
PubChem (CID)	2812
IUPHAR/BPS	2330
DrugBank	DB00257 Y
ChemSpider	2710 Y
UNII	G07GZ97H65 Y
KEGG	D00282 Y
ChEBI	CHEBI:3764 Y
ChEMBL	CHEMBL104 Y
ECHA InfoCard	100.041.589
Chemical and physical data
Formula	C22H17ClN2
Molar mass	344.837 g/mol
3D model (Jmol)	Interactive image
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 Y Key:VNFPBHJOKIVQEB-UHFFFAOYSA-N Y

Clotrimazole, sold under the brand name Canesten among others, is an antifungal medication. It is used to treat vaginal yeast infections, oral thrush, diaper rash, pityriasis 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.

Common side effects when taken by mouth include nausea and itchiness. When applied to the skin common side effects include redness and burning. 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 cell membrane.

Clotrimazole was discovered in 1969. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. It is available as a generic medication. The wholesale cost in the developing world as of 2014 is 0.20–0.86 USD per 20gm tube of cream. In the United States a course of treatment typically costs less than 25 USD.

It is commonly available without a prescription in various dosage forms, such as a cream, vaginal tablet, or as a prescription troche or throat lozenge (prescription only). Topically, clotrimazole is used for vulvovaginal candidiasis (yeast infection) or yeast infections of the skin. For vulvovaginal candidiasis (yeast infection), clotrimazole tablets and creams are inserted into the vagina. Troche or throat lozenge preparations are used for oropharyngeal candidiasis (oral thrush) or prophylaxis against oral thrush in neutropenic patients.