Clotrimazole

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Not to be confused with Chlormethiazole or Clomethiazole.
Clotrimazole
Clotrimazole.png
Clotrimazole-xtal-3D-balls.png
Systematic (IUPAC) name
1-[(2-Chlorophenyl)(diphenyl)methyl]-1H-imidazole
Clinical data
Trade names Lotrimin, Desenex, Canesten
AHFS/Drugs.com Monograph
MedlinePlus a682753
Pregnancy
category
  • AU: A
  • C (oral) and B (topical) (US)
Routes of
administration
topical, throat lozenge
Legal status
Legal status
  • US: OTC (topical), prescription (oral)
Pharmacokinetic data
Bioavailability Poor oral absorption (lozenge), negligible absorption through intact skin (topical)
Protein binding 90%
Metabolism hepatic
Biological half-life 2 hours
Identifiers
CAS Number 23593-75-1 YesY
ATC code A01AB18 (WHO) D01AC01 (WHO) G01AF02 (WHO) QJ02AB90 (WHO)
PubChem CID 2812
IUPHAR/BPS 2330
DrugBank DB00257 YesY
ChemSpider 2710 YesY
UNII G07GZ97H65 YesY
KEGG D00282 YesY
ChEBI CHEBI:3764 YesY
ChEMBL CHEMBL104 YesY
Chemical data
Formula C22H17ClN2
Molar mass 344.837 g/mol
  (verify)

Clotrimazole (brand name Canesten or Lotrimin) is an antifungal medication commonly used in the treatment of fungal infections (of both humans and other animals) such as vaginal yeast infections, oral thrush, and ringworm. It is also used to treat athlete's foot and jock itch.[1] It is on the World Health Organization's List of Essential Medicines, the most important medications needed in a basic health system.[2]

Medical uses[edit]

Canesten (clotrimazole) antifungal cream

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.

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). Although FDA approved, clotrimazole-betamethasone combination cream also is not the preferred treatment for dermatophyte infections as it can lead to increased side effects because of the potent topical glucocorticoid. Although the combination of a glucocorticoid and antifungal agent is commonly used, the combined agents can partially suppress a superficial dermatophyte infection but may ultimately make the infection more severe and deeper, requiring systemic antifungal agents to treat the disease. The use of this combination cream should be avoided because it can lead to treatment failures and skin atrophy related to prolonged topical glucocorticoid use, and has an increased cost compared with topical antifungal agents alone. It can be effective in treating chronic paronychia. The preferred treatment of tinea infections is therefore with clotrimazole monotherapy.[4]

Topical and oral clotrimazole can be used in both adults and children.

Additionally, clotrimazole may be used to treat the sickling of cells (related to sickle cell anemia).[5][6]

Pregnancy[edit]

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.[7]

Side effects[edit]

Side effects of the oral formulation include itching, nausea, and vomiting. >10% of patients using the oral formulation may have abnormal liver function tests. Side effects include rash, hives, blisters, burning, itching, peeling, redness, swelling, pain or other signs of skin irritation.[8] 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 [9][10][11]

Clotrimazole creams and suppositories contain oil which may weaken latex condoms and diaphragms.[12]

Drug interactions[edit]

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.[13]

Mechanism of action[edit]

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.[14][15]

References[edit]

  1. ^ American Society of Health-System Pharmacists, Inc. "Clotrimazole". NIH. Retrieved 19 April 2014. 
  2. ^ "WHO Model List of EssentialMedicines" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014. 
  3. ^ "Clotrimazole: MedlinePlus Drug Information". The American Society of Health-System Pharmacists, Inc. Retrieved 17 April 2014. 
  4. ^ Moriarty, B; Hay, R; Morris-Jones, R (10 July 2012). "The diagnosis and management of tinea.". BMJ (Clinical research ed.). 345: e4380. PMID 22782730. 
  5. ^ Marieb & Hoehn, (2010). Human Anatomy and Physiology, p. 643. Toronto: Pearson
  6. ^ Rodgers, Griffin. "Hydroxyurea and other disease-modifying therapies in sickle cell disease". UpToDate. Retrieved 14 April 2014. 
  7. ^ "Diseases Characterized by Vaginal Discharge". CDC. Retrieved 17 April 2014. 
  8. ^ Template:Cite web http://www.drugs.com/cons/canesten-topical.html
  9. ^ "Clotrimazole: MedlinePlus Drug Information". The American Society of Health-System Pharmacists, Inc. Retrieved 17 April 2014. 
  10. ^ "Clotrimazole". DrugBank. Retrieved 17 April 2014. 
  11. ^ "Clotrimazole (Oral)". Lexicomp Online. Retrieved 17 April 2014. 
  12. ^ "Diseases Characterized by Vaginal Discharge". CDC. Retrieved 17 April 2014. 
  13. ^ "Clotrimazole". DrugBank. Retrieved 17 April 2014. 
  14. ^ "Clotrimazole (Oral)". Lexicomp Online. Retrieved 17 April 2014. 
  15. ^ "Clotrimazole". DrugBank. Retrieved 17 April 2014.