Clotrimazole

Last updated

Clotrimazole
Clotrimazole.svg
Clotrimazole-xtal-3D-balls.png
Clinical data
Trade names Lotrimin, others
AHFS/Drugs.com Monograph
MedlinePlus a682753
License data
Pregnancy
category
  • AU:A
Routes of
administration 		Topical, throat lozenge
ATC code
Legal status
Legal status
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
  • 1-[(2-Chlorophenyl)(diphenyl)methyl]-1H-imidazole
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.041.589 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C22H17ClN2
Molar mass 344.84 g·mol−1
3D model (JSmol)
Melting point 147 to 149 °C (297 to 300 °F)
  • Clc1ccccc1C(c2ccccc2)(c3ccccc3)n4ccnc4
  • 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

Clotrimazole, sold under the brand name Lotrimin, among others, is an antifungal medication. [5] 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. [5] It is in the azole class of medications and works by disrupting the fungal cell membrane. [5] It can be taken by mouth or applied as a cream to the skin or in the vagina. [5]

Contents

Common side effects of clotrimazole taken by mouth include nausea and itchiness. [5] When it is applied to the skin, common side effects include redness and a burning sensation. [5] 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. [5]

Clotrimazole, originally known as BAY b 5097, was discovered in 1969. [6] It is on the World Health Organization's List of Essential Medicines. [7] It is available as a generic medication. [5] In 2023, it was the 259th most commonly prescribed medication in the United States, with more than 1 million prescriptions. [8] [9]

Medical uses

It is available without a prescription in various dosage forms, such as a topical cream, ointment, or vaginal suppository. [5] [10]

An effective treatment option for mixed infectious vaginitis is a combination of clotrimazole and metronidazole. [11]

Topical clotrimazole is usually not effective in the treatment of fungal infections of the scalp or nails. [12]

Throat lozenge preparations are used for oropharyngeal candidiasis (oral thrush) or prevention of oral thrush in people with neutropenia. [13]

Clotrimazole may be compounded with a glucocorticoid, such as betamethasone, in a topical cream for the treatment of tinea corporis (ringworm), tinea cruris (jock itch), and tinea pedis (athlete's foot). Although temporary relief and partial suppression of symptoms may be observed with the combination therapy, glucocorticoids can elicit an immunosuppressive response and rebound effect that results in more severe infection typically requiring systemic antifungal agents to treat the disease. Combination creams are best avoided to improve treatment outcomes, reduce the possibility of skin atrophy associated with prolonged topical glucocorticoid use, and limit the cost of treatment. It can be effective in treating chronic paronychia. The preferred treatment of tinea infections is therefore clotrimazole monotherapy. [14]

Topical clotrimazole cream, when combined with mechanical reduction of the nail, has been demonstrated to be effective in the treatment of onychomycosis - a fungal infection of the fingernails and toenails. [15]

Additionally, clotrimazole may be used to treat the sickling of cells (related to sickle cell anemia). [16] [17]

Pregnancy

Small amounts of clotrimazole may be absorbed systemically following topical and vaginal administration. However, topical clotrimazole is still considered safe to use to treat yeast infections in pregnant women and is a safer alternative to other antifungals. [18] [19]

Side effects

Side effects of the oral formulation include itching, nausea, and vomiting. Less than 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. [5] For this reason, liver function tests should be monitored periodically when taking oral clotrimazole (troche). When used to treat vulvovaginal candidiasis (yeast infection), less than 10% of patients have vulvar or vaginal burning sensation. Less than 1% of patients have the following side effects: burning or itching of the penis of a sexual partner; polyuria; vulvar itching, soreness, edema, or discharge. [20] [10]

Clotrimazole creams and suppositories contain oil which may weaken latex condoms and diaphragms. [19]

Interactions

There are no known significant drug interactions with topical clotrimazole. [5]

Pharmacology

Pharmacodynamics

Clotrimazole is an imidazole derivative that works by inhibiting the growth of individual Candida or fungal cells by altering the permeability of the fungal cell wall. [10] The drug impairs the biosynthesis of ergosterol, a critical component of the fungal cell membrane, by inhibiting the P450 enzyme lanosterol 14-alpha demethylase. [21] Clotrimazole may slow fungal growth or result in fungal cell death. [5]

Society and culture

Economics

Canesten brand Clotrimazole antifungal cream Canesten.jpg
Canesten brand Clotrimazole antifungal cream

Clotrimazole is available as a generic medication, [5] and in 2016, Canesten brand clotrimazole was one of the biggest-selling branded over-the-counter medications sold in Great Britain, with sales of £39.2 million. [22]

References

  1. ↑ "Product monograph brand safety updates". Health Canada . 6 June 2024. Retrieved 8 June 2024.
  2. ↑ "Lotrimin Antifungal- clotrimazole cream". DailyMed. 6 December 2024. Retrieved 29 September 2025.
  3. ↑ "Lotrimin- clotrimazole cream". DailyMed. 6 December 2024. Retrieved 29 September 2025.
  4. ↑ "Lotrimin- clotrimazole cream". DailyMed. 6 December 2024. Retrieved 29 September 2025.
  5. 1 2 3 4 5 6 7 8 9 10 11 12 13 American Society of Health-System Pharmacists (8 February 2016). "Clotrimazole Monograph for Professionals". Drugs.com. Archived from the original on 28 October 2016. Retrieved 28 October 2016.
  6. ↑ Walker SR (2012). Trends and Changes in Drug Research and Development. Springer Science & Business Media. p. 109. ISBN   978-94-009-2659-2. Archived from the original on 14 September 2016.
  7. ↑ World Health Organization (2025). The selection and use of essential medicines, 2025: WHO Model List of Essential Medicines, 24th list. Geneva: World Health Organization. doi: 10.2471/B09474 . hdl: 10665/382243 . License: CC BY-NC-SA 3.0 IGO.
  8. ↑ "The Top 300 of 2023". ClinCalc. Archived from the original on 17 August 2025. Retrieved 17 August 2025.
  9. ↑ "Clotrimazole Drug Usage Statistics, United States, 2014 - 2023". ClinCalc. Retrieved 17 August 2025.
  10. 1 2 3 "Clotrimazole (Oral)". Lexicomp Online. Archived from the original on 23 January 2015. Retrieved 17 April 2014.
  11. ↑ Huang Y, Shen C, Shen Y, Cui H (January 2024). "Assessing the Efficacy of Clotrimazole and Metronidazole Combined Treatment in Vaginitis: A Meta-Analysis" (PDF). Altern Ther Health Med. 30 (1): 186–191. PMID   37773671 . Retrieved 8 August 2024.
  12. ↑ Khatter N, Khan M (19 January 2025). "Clotrimazole". National Library of Medicine. NIH. PMID   32809478 . Retrieved 24 March 2025.
  13. ↑ "UpToDate". www.uptodate.com. Archived from the original on 17 October 2019. Retrieved 7 August 2019.
  14. ↑ Moriarty B, Hay R, Morris-Jones R (July 2012). "The diagnosis and management of tinea" (PDF). BMJ. 345 e4380. doi:10.1136/bmj.e4380. PMID   22782730. S2CID   38106083 . Retrieved 8 August 2024.
  15. ↑ Davies KJ (1 March 2006). "Study to determine the efficacy of Clotrimazole 1% cream for the treatment of onychomycosis in association with the mechanical reduction of the nail plate" . The Foot. 16 (1): 19–22. doi:10.1016/j.foot.2005.10.004. ISSN   0958-2592.
  16. ↑ Marieb EN, Hoehn K. Human Anatomy and Physiology. Toronto: Pearson. p. 643.
  17. ↑ Rodgers G. "Hydroxyurea and other disease-modifying therapies in sickle cell disease". UpToDate. Archived from the original on 15 April 2014. Retrieved 14 April 2014.
  18. ↑ Patel VM, Schwartz RA, Lambert WC (September 2017). "Topical antiviral and antifungal medications in pregnancy: a review of safety profiles". Journal of the European Academy of Dermatology and Venereology. 31 (9): 1440–1446. doi:10.1111/jdv.14297. PMID   28449377. S2CID   544751.
  19. 1 2 "Diseases Characterized by Vaginal Discharge". U.S. Centers for Disease Control and Prevention (CDC). Archived from the original on 28 April 2014. Retrieved 17 April 2014.
  20. ↑ "Clotrimazole: MedlinePlus Drug Information". The American Society of Health-System Pharmacists, Inc. Archived from the original on 18 April 2014. Retrieved 17 April 2014.
  21. ↑ Crowley PD, Gallagher HC (September 2014). "Clotrimazole as a pharmaceutical: past, present and future". Journal of Applied Microbiology. 117 (3): 611–617. doi:10.1111/jam.12554. PMID   24863842. Archived from the original on 25 January 2024. Retrieved 19 October 2023.
  22. ↑ "A breakdown of the over-the-counter medicines market in Britain in 2016". The Pharmaceutical Journal. 12 February 2021. Retrieved 29 September 2025.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.