Clotrimazole
Systematic (IUPAC) name
1-[(2-Chlorophenyl)(diphenyl)methyl]-1H-imidazole
Clinical data
Trade names Lotrimin, Desenex, Canesten
AHFS/Drugs.com
MedlinePlus
Pregnancy
category
  • AU: A
  • C (oral) and B (topical) (US)
Legal status
  • US: OTC (topical), prescription (oral)
Routes of
administration
topical, troche
Pharmacokinetic data
Bioavailability Poor oral absorption (troche), negligible absorption through intact skin (topical)
Protein binding 90%
Metabolism hepatic
Biological half-life 2 hours
Identifiers
CAS Registry Number  YesY
ATC code A01 D01 G01 QJ02
PubChem CID:
IUPHAR/BPS
DrugBank  YesY
ChemSpider  YesY
UNII  YesY
KEGG  YesY
ChEBI  YesY
ChEMBL  YesY
Chemical data
Formula C22H17ClN2
Molecular mass 344.837 g/mol
 YesY   

Clotrimazole (brand name Canesten or Lotrimin) is an health system.[2]

Medical uses

Canesten (clotrimazole) antifungal cream

It is commonly available as an over-the-counter substance 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.

Clotrimazole is usually used 5 times daily for 14 days for oral thrush, twice daily for 2 to 8 weeks for skin infections, and once daily for 3 or 7 days for vaginal infections.[3]

Clotrimazole is also commonly used in conjunction with betamethasone as a topical cream for tinea corporis (ringworm), tinea cruris (jock itch), or tinea pedis (athlete's foot).

Topical and oral clotrimazole can be used in both adult and pediatric populations.

Additionally, clotrimazole may be used to treat the sickling of cells (related to sickle cell anemia).[4][5]

Pregnancy

Small amounts of clotrimazole may be absorbed systemically following topical and vaginal administration. However, this may still be used to treat yeast infections in pregnant women.[6]

Side effects

Side effects of the oral formulation include itching, nausea, and vomiting. >10% of patients using the oral formulation may have abnormal liver function tests. For this reason, liver function tests should be monitored periodically when taking the oral clotrimazole (troche). When used to treat vulvovaginal candidiasis (yeast infection), <10% of patient have vulvar or vaginal burning sensation. <1% of patients have the following side effects: Burning or itching of penis of sexual partner; polyuria; vulvar itching, soreness, edema, or discharge [7] [8] [9]

Clotrimazole creams and suppositories contain oil which may weaken latex condoms and diaphragms.[10]

Drug interactions

There are no known significant drug interactions with topical clotrimazole. However, with oral (troche) clotrimazole, there are multiple interactions as the medication is a CYP450 enzyme inhibitor, primarily CYP3A4. Thus, any medication that is metabolized by the CYP3A4 enzyme will potentially have elevated levels when oral clotrimazole is used. The prescribing physician should be aware of any medication the patient is taking prior to starting oral clotrimazole. Certain medications should not be taken with oral clotrimazole.[11]

Mechanism of action

Clotrimazole works to kill individual Candida or fungal cells by altering the permeability of the fungal cell wall. It binds to phospholipids in the cell membrane and inhibits the biosynthesis of ergosterol and other sterols required for cell membrane production. This leads to the cell's death via loss of intracellular elements.[12] [13]

References

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  4. ^ Marieb & Hoehn, (2010). Human Anatomy and Physiology, p. 643. Toronto: Pearson
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