Clotrimazole

Clotrimazole, sold under the brand name Canesten among others,

is an antifungal medication.[1] It is used to treat vaginal yeast
Clotrimazole
infections, oral thrush, diaper rash, pityriasis versicolor, and types of
ringworm including athlete's foot and jock itch.[1] It can be taken by
mouth or applied as a cream to the skin or in the vagina.[1]

Common side effects when taken by mouth include nausea and

itchiness.[1] When applied to the skin, common side effects include
redness and burning.[1] In pregnancy, use on the skin or in the
vagina is believed to be safe.[1] There is no evidence of harm when
used by mouth during pregnancy but this has been less well
studied.[1] When used by mouth, greater care should be taken in
those with liver problems.[1] It is in the azole class of medications
and works by disrupting the fungal cell membrane.[1]

Clotrimazole was discovered in 1969.[2] It is on the World Health

Organization's List of Essential Medicines, the safest and most
effective medicines needed in a health system.[3] It is available as a
generic medication.[1] The wholesale cost in the developing world as
of 2014 is 0.20–0.86 USD per 20 gram tube of cream.[4] In the
United States, a course of treatment typically costs less than
US$25.[5]

Contents Clinical data

Medical uses Trade names Desenex,
Pregnancy Canesten, others
Side effects AHFS/Drugs.com Monograph (http
Interactions s://www.drugs.co
m/monograph/clo
Pharmacology
Pharmacodynamics trimazole.html)
MedlinePlus a682753 (https://
Society and culture
medlineplus.gov/
References druginfo/meds/a6
External links 82753.html)
Pregnancy AU: A
category
Medical uses C (by mouth) and
B (topical) (US)
It is commonly available without a prescription in various dosage Routes of Topical, throat
forms, such as a topical cream, ointment, or vaginal suppository. It is administration lozenge
also available as an oral troche or throat lozenge as a prescription
only. Topically, clotrimazole is used for vulvovaginal candidiasis ATC code A01AB18 (WHO
(yeast infection) or yeast infections of the skin. For vulvovaginal (https://www.who
candidiasis (yeast infection), clotrimazole tablets and creams are cc.no/atc_ddd_in
inserted into the vagina. Topical clotrimazole is usually not effective dex/?code=A01A
in treatment of fungal infections of the scalp or nails. When using B18)) D01AC01
over-the-counter drug clotrimazole products, use should be
(WHO (https://ww
discontinued if condition does not improve after treatment for 2
w.whocc.no/atc_d
weeks for jock itch or after 4 weeks for athlete's foot or ringworm.[6]
dd_index/?code=
Throat lozenge preparations are used for oropharyngeal candidiasis D01AC01))
(oral thrush) or prevention of oral thrush in people with G01AF02 (WHO
neutropenia.[6] (https://www.who
cc.no/atc_ddd_in
Clotrimazole is usually used 5 times daily for 14 days for oral dex/?code=G01A
thrush, twice daily for 2 to 8 weeks for skin infections, and once
F02)) QJ02AB90
daily for 3 or 7 days for vaginal infections.[7]
(WHO (https://ww
Clotrimazole may be compounded with a glucocorticoid, such as w.whocc.no/atcve
betamethasone, in a topical cream for the treatment of tinea corporis t/atcvet_index/?c
(ringworm), tinea cruris (jock itch) and tinea pedis (athlete's foot). ode=QJ02AB90))
Although FDA approved, clotrimazole-betamethasone combination
Legal status
cream is not the preferred treatment for dermatophyte infections due
to increased side effects from the topical glucocorticoid. Although Legal status US: OTC (topical),
temporary relief and partial suppression of symptoms may be ℞-only (by mouth)
observed with the combination therapy, glucocorticoids can elicit an
Pharmacokinetic data
immunosuppressive response and rebound effect that results in more
severe infection typically requiring systemic antifungal agents to Bioavailability Poor absorption
treat the disease. Combination creams are best avoided in order to by mouth
improve treatment outcome, reduce the possibility of skin atrophy (lozenge),
associated with prolonged topical glucocorticoid use, and to limit the negligible
cost of treatment. It can be effective in treating chronic paronychia. absorption
The preferred treatment of tinea infections is therefore with
through intact
clotrimazole monotherapy.[8]
skin (topical)
Topical and oral clotrimazole can be used in both adults and Protein binding 90%
children. Metabolism Liver
Additionally, clotrimazole may be used to treat the sickling of cells Elimination 2 hours
(related to sickle cell anemia).[9][10] half-life
Identifiers
It can be taken by mouth as a lozenge or troche or applied as a IUPAC name
topical cream to the skin or in the vagina.[1][11]
1-[(2-Chlorophenyl)(diphenyl)methyl]-1H-imida

zole
Pregnancy CAS Number 23593-75-1 (htt
Topical clotrimazole is categorized as pregnancy category B.[12] p://www.common
Small amounts of clotrimazole may be absorbed systemically chemistry.org/Ch
following topical and vaginal administration. However, topical emicalDetail.asp
clotrimazole is still considered safe to use to treat yeast infections in x?ref=23593-75-
pregnant women and is a safer alternative to other antifungals.[13][12] 1)
PubChem CID 2812 (https://pub
Side effects chem.ncbi.nlm.ni
Side effects of the oral formulation include itching, nausea, and h.gov/compound/
vomiting. >10% of patients using the oral formulation may have 2812)
abnormal liver function tests. Side effects include rash, hives,
IUPHAR/BPS 2330 (http://www.
blisters, burning, itching, peeling, redness, swelling, pain or other
signs of skin irritation.[1] For this reason, liver function tests should guidetopharmacol
be monitored periodically when taking the oral clotrimazole (troche). ogy.org/GRAC/Li
When used to treat vulvovaginal candidiasis (yeast infection), <10% gandDisplayForw
of patient have vulvar or vaginal burning sensation. <1% of patients ard?ligandId=233
have the following side effects: Burning or itching of penis of sexual 0)
partner; polyuria; vulvar itching, soreness, edema, or discharge
[7][14][11] DrugBank DB00257 (https://
www.drugbank.c
Clotrimazole creams and suppositories contain oil which may a/drugs/DB0025
weaken latex condoms and diaphragms.[13] 7)

For topical formulations, should be used externally and should be ChemSpider 2710 (http://www.
discontinued if irritation or sensitivity develops at the site of chemspider.com/
administration.[15] Chemical-Structu
re.2710.html)
Interactions UNII G07GZ97H65 (htt
ps://fdasis.nlm.ni
There are no known significant drug interactions with topical h.gov/srs/srsdirec
clotrimazole. However, with oral (troche) clotrimazole, there are t.jsp?regno=G07
multiple interactions as the medication is a CYP450 enzyme GZ97H65)
inhibitor, primarily CYP3A4. Thus, any medication that is
metabolized by the CYP3A4 enzyme will potentially have elevated KEGG D00282 (https://w
levels when oral clotrimazole is used. The prescribing physician ww.kegg.jp/entry/
should be aware of any medication the patient is taking prior to D00282)
starting oral clotrimazole. Certain medications should not be taken
ChEBI CHEBI:3764 (http
with oral clotrimazole.[14]
s://www.ebi.ac.u
k/chebi/searchId.
Pharmacology do?chebiId=CHE
BI:3764)
Pharmacodynamics ChEMBL ChEMBL104 (http
s://www.ebi.ac.u
Clotrimazole is an imidazole derivative which works by inhibiting k/chembldb/inde
the growth of individual Candida or fungal cells by altering the x.php/compound/i
permeability of the fungal cell wall.[11] It binds to phospholipids in
nspect/ChEMBL1
the cell membrane and inhibits the biosynthesis of ergosterol and
04)
other sterols required for cell membrane production.[11][14]
Clotrimazole may slow fungal growth or result in fungal cell CompTox DTXSID7029871
death.[1] Dashboard (EPA)
(https://comptox.e
pa.gov/dashboar
Society and culture d/DTXSID702987
1)
It is available as a generic medication.[1] The wholesale cost in the ECHA InfoCard 100.041.589 (http
developing world as of 2014 is 0.20–0.86 USD per 20gm tube of s://echa.europa.e
cream.[4] In the United States treatment typically costs less than u/substance-infor
US$25.[5] In 2016 Canesten was one of the biggest selling branded
over-the-counter medications sold in Great Britain, with sales of mation/-/substanc
£39.2 million.[16] einfo/100.041.58
9)
Chemical and physical data
Formula C22H17ClN2
Molar mass 344.84 g·mol−1
3D model Interactive image
(JSmol)
(https://chemapp
s.stolaf.edu/jmol/j
mol.php?model=
Clc1ccccc1C%28
c2ccccc2%29%2
8c3ccccc3%29n4
ccnc4)
Melting point 147 to 149 °C
(297 to 300 °F)
SMILES
Clc1ccccc1C(c2ccccc2)(c3ccccc3)n4ccnc4

InChI
InChI=1S/C22H17ClN2/c23-21-14-8-7-13-20(2
1)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

(verify)

Clotrimazole (Canesten) antifungal

cream

References
1. American Society of Health-System Pharmacists (8 February 2016). "Clotrimazole Monograph
for Professionals" (https://www.drugs.com/monograph/clotrimazole.html). www.drugs.com.
Archived (https://web.archive.org/web/20161028154036/https://www.drugs.com/monograph/cl
otrimazole.html) from the original on 28 October 2016. Retrieved 28 October 2016.
2. Walker SR (2012). Trends and Changes in Drug Research and Development (https://books.go
ogle.com/books?id=FB_2CAAAQBAJ&pg=PA109). Springer Science & Business Media.
p. 109. ISBN 9789400926592. Archived (https://web.archive.org/web/20160914021552/https://
books.google.com/books?id=FB_2CAAAQBAJ&pg=PA109) from the original on 2016-09-14.
 3. World Health Organization (2019). World Health Organization model list of essential
medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771 (https://hdl.h
andle.net/10665%2F325771). WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
4. "Clotrimazole" (http://mshpriceguide.org/en/single-drug-information/?DMFId=198&searchYear=
2014). International Drug Price Indicator Guide. Archived (https://web.archive.org/web/201705
10161841/http://mshpriceguide.org/en/single-drug-information/?DMFId=198&searchYear=201
4) from the original on 10 May 2017. Retrieved 28 October 2016.
5. Tarascon Pharmacopoeia 2016 Professional Desk Reference Edition (https://books.google.co
m/books?id=iu7PDAAAQBAJ&pg=PA176). Jones & Bartlett Publishers. 2016. p. 176.
ISBN 9781284095302. Archived (https://web.archive.org/web/20161028155043/https://books.g
oogle.com/books?id=iu7PDAAAQBAJ&pg=PA176) from the original on 2016-10-28.
6. "UpToDate" (https://www.uptodate.com/contents/clotrimazole-topical-drug-information?search=
clotrimazole&source=panel_search_result&selectedTitle=1~47&usage_type=panel&display_ra
nk=1#F8011628). www.uptodate.com. Retrieved 2019-08-07.
7. "Clotrimazole: MedlinePlus Drug Information" (https://www.nlm.nih.gov/medlineplus/druginfo/m
eds/a682753.html). The American Society of Health-System Pharmacists, Inc. Archived (http
s://web.archive.org/web/20140418035653/http://www.nlm.nih.gov/medlineplus/druginfo/meds/a
682753.html) from the original on 18 April 2014. Retrieved 17 April 2014.
8. Moriarty B, Hay R, Morris-Jones R (July 2012). "The diagnosis and management of tinea".
BMJ. 345: e4380. doi:10.1136/bmj.e4380 (https://doi.org/10.1136%2Fbmj.e4380).
PMID 22782730 (https://pubmed.ncbi.nlm.nih.gov/22782730).
9. Marieb EN, Hoehn K. Human Anatomy and Physiology. Toronto: Pearson. p. 643.
10. Rodgers G. "Hydroxyurea and other disease-modifying therapies in sickle cell disease" (http://
www.uptodate.com/contents/hydroxyurea-and-other-disease-modifying-therapies-in-sickle-cell-
disease?source=search_result&search=hydroxyurea&selectedTitle=1~87). UpToDate.
Archived (https://web.archive.org/web/20140415042143/http://www.uptodate.com/contents/hyd
roxyurea-and-other-disease-modifying-therapies-in-sickle-cell-disease?source=search_result&
search=hydroxyurea&selectedTitle=1~87) from the original on 15 April 2014. Retrieved
14 April 2014.
11. "Clotrimazole (Oral)" (http://online.lexi.com/lco/action/doc/retrieve/docid/patch_f/1772079).
Lexicomp Online. Archived (https://web.archive.org/web/20150123091514/http://online.lexi.co
m/lco/action/doc/retrieve/docid/patch_f/1772079) from the original on 23 January 2015.
Retrieved 17 April 2014.
12. 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 (https://doi.org/10.1
111%2Fjdv.14297). PMID 28449377 (https://pubmed.ncbi.nlm.nih.gov/28449377).
13. "Diseases Characterized by Vaginal Discharge" (https://www.cdc.gov/std/treatment/2010/vagin
al-discharge.htm). CDC. Archived (https://web.archive.org/web/20140428171000/http://www.c
dc.gov/sTD/treatment/2010/vaginal-discharge.htm) from the original on 28 April 2014.
Retrieved 17 April 2014.
14. "Clotrimazole" (http://www.drugbank.ca/drugs/DB00257). DrugBank. Archived (https://web.arch
ive.org/web/20140417070045/http://www.drugbank.ca/drugs/DB00257) from the original on 17
April 2014. Retrieved 17 April 2014.
15. "DailyMed - CLOTRIMAZOLE ANTIFUNGAL- clotrimazole cream" (https://dailymed.nlm.nih.go
v/dailymed/drugInfo.cfm?setid=e03d9368-e1b4-4e37-87e4-3ee241916aed).
dailymed.nlm.nih.gov. Retrieved 2019-08-07.
16. "A breakdown of the over-the-counter medicines market in Britain in 2016" (http://www.pharma
ceutical-journal.com/20202662.article?amp;utm_medium=email&). Pharmaceutical Journal. 28
April 2017. Retrieved 29 May 2017.
External links
"Clotrimazole" (https://druginfo.nlm.nih.gov/drugportal/name/clotrimazole). Drug Information
Portal. U.S. National Library of Medicine.

Retrieved from "https://en.wikipedia.org/w/index.php?title=Clotrimazole&oldid=962990181"

This page was last edited on 17 June 2020, at 04:39 (UTC).

Text is available under the Creative Commons Attribution-ShareAlike License; additional terms may apply. By using
this site, you agree to the Terms of Use and Privacy Policy. Wikipedia® is a registered trademark of the Wikimedia
Foundation, Inc., a non-profit organization.