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Clotrimazole: Wikis

  

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Clotrimazole
Systematic (IUPAC) name
1-[(2-chlorophenyl)(diphenyl)methyl]-1H-imidazole
Identifiers
CAS number 23593-75-1
ATC code A01AB18 D01AC01 G01AF02 QJ02AB90
PubChem 2812
DrugBank APRD00244
ChemSpider 2710
Chemical data
Formula C 22H17ClN2  
Mol. mass 344.837 g/mol
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability Poorly and erratically absorbed orally
Protein binding 90%
Metabolism hepatic
Half life 2 hours
Excretion  ?
Therapeutic considerations
Pregnancy cat. A(AU) C (oral) & B (topical) (US)
Legal status P (UK)
Routes topical
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Clotrimazole is an antifungal medication commonly used in the treatment of fungal infections of both humans and animals such as vaginal yeast infections, oral thrush, and ringworm. It is also used to treat athlete's foot and jock itch.

Contents

Indications and formulations

Canesten cream (AU)
Canesten powder (UK)

It is commonly available as an over-the-counter substance in various dosage forms, such as a cream, and also (especially in the case of ear infection) as a combination medicine. It is also available as a troche (prescription only). For ear infection it is often applied in liquid form, as ear drops. Fungal infections can be slow to clear up, so the usual course for an anti-fungal agent is generally longer than the typical 3-7 days of an antibiotic.

Drug interactions

Potential for drug interactions with Clotrimazole oral exists, as it is a potent, specific inhibitor of cytochrome P450 oxidase and may alter the metabolism of other drugs.

Side effects

Occasionally may cause localised irritation of the skin with a mild burning sensation, redness and itching.

Production

This compound (3) is produced by alkylating imidazole (1) with o-chlorotrityl chloride (2) in acetone, with triethylamine as the base.[1]

Clotrimazole synthesis.svg

Environmental impact

Some research suggests that, in combination with other commonly used chemicals, clotrimazole has negative effects on the ocean environment, particularly microalgae.[2]

References

  1. ^ OSPAR Commission: Hazardous Substances Series: OSPAR background document on clotrimazole. OSPAR Publication 2005/199, 2005, ISBN 1-904426-38-7 (pdf, engl.)
  2. ^ Drug used to treat skin conditions is a marine pollutant

External links








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