Misplaced Pages

:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Clotrimazole: Difference between pages - Misplaced Pages

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
(Difference between pages)
Page 1
Page 2
Content deleted Content addedVisualWikitext
Revision as of 10:09, 6 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 464314030 of page Clotrimazole for the Chem/Drugbox validation project (updated: 'DrugBank').  Latest revision as of 22:28, 7 December 2024 edit 2601:642:c303:f370:314a:4b77:9003:c9b5 (talk) ce 
Line 1: Line 1:
{{Short description|Chemical compound}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{Distinguish|Clomethiazole|Chlormidazole|Co-trimoxazole}}
{{Use dmy dates|date=June 2022}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Drugbox {{Drugbox
| Verifiedfields = changed | Watchedfields = changed
| verifiedrevid = 460045551 | verifiedrevid = 464366359
| image = Clotrimazole.svg
| IUPAC_name = 1--1''H''-imidazole
| width =
| image = Clotrimazole.png
| width = 200 | alt =
| image2 = Clotrimazole-xtal-3D-balls.png | image2 = Clotrimazole-xtal-3D-balls.png
| width2 =
| alt2 =


<!--Clinical data--> <!-- Clinical data -->
| tradename = Lotriminaf, Mycelex | tradename = Desenex, CalmYourself, others
| Drugs.com = {{drugs.com|monograph|clotrimazole}} | Drugs.com = {{drugs.com|monograph|clotrimazole}}
| MedlinePlus = a682753 | MedlinePlus = a682753
| pregnancy_AU = A | pregnancy_AU = A
| pregnancy_category = C (oral) & B (topical) <small>(])</small> | pregnancy_category =
| routes_of_administration = ], ]
| legal_UK = P
| ATC_prefix = A01
| routes_of_administration = ]
| ATC_suffix = AB18
| ATC_supplemental = {{ATC|D01|AC01}} {{ATC|G01|AF02}} {{ATCvet|J02|AB90}}

| legal_CA = OTC
| legal_CA_comment = <ref>{{cite web | title=Product monograph brand safety updates | website=] | date=6 June 2024 | url=https://www.canada.ca/en/health-canada/services/drugs-health-products/drug-products/drug-product-database/label-safety-assessment-update/product-monograph-brand-safety-updates.html | access-date=8 June 2024}}</ref>
| legal_US = OTC
| legal_US_comment = (topical), Rx-only (by mouth)


<!--Pharmacokinetic data--> <!-- Pharmacokinetic data -->
| bioavailability = Poor absorption by mouth (lozenge), negligible absorption through intact skin (topical)
| bioavailability = Poorly and erratically absorbed orally
| protein_bound = 90% | protein_bound = 90%
| metabolism = ] | metabolism = ]
| elimination_half-life = 2 hours | elimination_half-life = 2 hours
| excretion =


<!--Identifiers--> <!-- Identifiers -->
| IUPHAR_ligand = 2330
| CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 23593-75-1 | CAS_number = 23593-75-1
| ATC_prefix = A01
| ATC_suffix = AB18
| ATC_supplemental = {{ATC|D01|AC01}} {{ATC|G01|AF02}} {{ATCvet|J02|AB90}}
| PubChem = 2812 | PubChem = 2812
| DrugBank_Ref = {{drugbankcite|changed|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00257 | DrugBank = DB00257
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
Line 43: Line 53:
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 104 | ChEMBL = 104
| synonyms =


<!--Chemical data--> <!--Chemical data-->
| IUPAC_name = 1--1''H''-imidazole
| C=22 | H=17 | Cl=1 | N=2
| C=22 | H=17 | Cl=1 | N=2
| molecular_weight = 344.837 g/mol
| smiles = Clc1ccccc1C(c2ccccc2)(c3ccccc3)n4ccnc4 | SMILES = Clc1ccccc1C(c2ccccc2)(c3ccccc3)n4ccnc4
| InChI = 1/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
| InChIKey = VNFPBHJOKIVQEB-UHFFFAOYAO
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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 | StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = VNFPBHJOKIVQEB-UHFFFAOYSA-N | StdInChIKey = VNFPBHJOKIVQEB-UHFFFAOYSA-N

<!--Physical data-->
| melting_point = 147
| melting_high = 149
}} }}

<!-- Definition and medical uses -->
'''Clotrimazole''', sold under the brand name '''Lotrimin''', among others, is an ].<ref name=AHFS2016/> It is used to treat ]s, ], ], ], and types of ] including ] and ].<ref name=AHFS2016/> It can be taken by mouth or applied as a cream to the skin or in the ].<ref name=AHFS2016>{{cite web|author1=American Society of Health-System Pharmacists|title=Clotrimazole Monograph for Professionals|url=https://www.drugs.com/monograph/clotrimazole.html|website=www.drugs.com|access-date=28 October 2016|date=8 February 2016|url-status=live|archive-url=https://web.archive.org/web/20161028154036/https://www.drugs.com/monograph/clotrimazole.html|archive-date=28 October 2016}}</ref>

<!-- Side effects and mechanism -->
Common ]s when taken by mouth include nausea and itchiness.<ref name=AHFS2016/> When applied to the skin, common side effects include redness and a burning sensation.<ref name=AHFS2016/> In ], use on the skin or in the vagina is believed to be safe.<ref name=AHFS2016/> There is no evidence of harm when used by mouth during pregnancy but this has been less well studied.<ref name=AHFS2016/> When used by mouth, greater care should be taken in those with liver problems.<ref name=AHFS2016/> It is in the ] class of medications and works by disrupting the fungal ].<ref name=AHFS2016/>

<!-- History and culture -->
Clotrimazole was discovered in 1969.<ref name=Wal2012>{{cite book| vauthors = Walker SR |title=Trends and Changes in Drug Research and Development|date=2012|publisher=Springer Science & Business Media|isbn=9789400926592|page=109|url=https://books.google.com/books?id=FB_2CAAAQBAJ&pg=PA109|language=en|url-status=live|archive-url=https://web.archive.org/web/20160914021552/https://books.google.com/books?id=FB_2CAAAQBAJ&pg=PA109|archive-date=14 September 2016}}</ref> It is on the ].<ref name="WHO21st">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 21st list 2019 | year = 2019 | hdl = 10665/325771 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO | hdl-access=free }}</ref> It is available as a ].<ref name=AHFS2016/> In 2021, it was the 273rd most commonly prescribed medication in the United States, with more than 900,000 prescriptions.<ref>{{cite web | title=The Top 300 of 2021 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=14 January 2024 | archive-date=15 January 2024 | archive-url=https://web.archive.org/web/20240115223848/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{cite web | title = Clotrimazole - Drug Usage Statistics | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Clotrimazole | access-date = 14 January 2024 | archive-date = 18 January 2024 | archive-url = https://web.archive.org/web/20240118044807/https://clincalc.com/DrugStats/Drugs/Clotrimazole | url-status = live }}</ref>

==Medical uses==
It is commonly available ] in various ]s, such as a topical cream, ointment, or vaginal suppository.<ref name="AHFS2016" /><ref name="Clotrimazole Oral">{{cite web |title=Clotrimazole (Oral) |url=http://online.lexi.com/lco/action/doc/retrieve/docid/patch_f/1772079 |url-status=live |archive-url=https://web.archive.org/web/20150123091514/http://online.lexi.com/lco/action/doc/retrieve/docid/patch_f/1772079 |archive-date=23 January 2015 |access-date=17 April 2014 |publisher=Lexicomp Online}}</ref> It is also available as an oral troche or ] as a prescription only. Topically, clotrimazole is used for ] (yeast infection) or yeast infections of the skin. For vulvovaginal candidiasis, clotrimazole tablets and creams are inserted into the vagina.{{medical citation needed|date=February 2024}}

An effective treatment option for mixed infectious vaginitis is a combination of clotrimazole and ].<ref name="pmid37773671">{{cite journal |vauthors=Huang Y, Shen C, Shen Y, Cui H |url=https://alternative-therapies.com/oa/index.html?fid=8973 |access-date=8 August 2024 |format=PDF |title=Assessing the Efficacy of Clotrimazole and Metronidazole Combined Treatment in Vaginitis: A Meta-Analysis |journal=Altern Ther Health Med |volume=30 |issue=1 |pages=186–191 |date=January 2024 |pmid=37773671}}</ref>

Topical clotrimazole is usually not effective in the treatment of fungal infections of the scalp or nails.{{Citation needed|date=October 2019}} When using ] clotrimazole products, use should be discontinued if the condition does not improve after treatment for 2 weeks for jock itch or after 4 weeks for athlete's foot or ringworm.<ref name="UpToDate">{{cite web|url=https://www.uptodate.com/contents/clotrimazole-topical-drug-information?search=clotrimazole&source=panel_search_result&selectedTitle=1~47&usage_type=panel&display_rank=1#F8011628|title=UpToDate|website=www.uptodate.com|access-date=7 August 2019|archive-date=17 October 2019|archive-url=https://web.archive.org/web/20191017175436/https://www.uptodate.com/contents/clotrimazole-topical-drug-information?search=clotrimazole&source=panel_search_result&selectedTitle=1~47&usage_type=panel&display_rank=1#F8011628|url-status=live}}</ref>

Throat lozenge preparations are used for oropharyngeal candidiasis (]) or prevention of oral thrush in people with ].<ref name="UpToDate"/>

Clotrimazole is usually used five 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.<ref name="nlm.nih.gov">{{cite web|title=Clotrimazole: MedlinePlus Drug Information|url=https://www.nlm.nih.gov/medlineplus/druginfo/meds/a682753.html|publisher=The American Society of Health-System Pharmacists, Inc|access-date=17 April 2014|url-status=live|archive-url=https://web.archive.org/web/20140418035653/http://www.nlm.nih.gov/medlineplus/druginfo/meds/a682753.html|archive-date=18 April 2014}}</ref>

Clotrimazole may be compounded with a ], such as ], in a topical cream for the treatment of ] (ringworm), ] (jock itch) and tinea pedis (]). Although FDA-approved, clotrimazole–betamethasone combination cream is not the preferred treatment for dermatophyte infections due to increased side effects from the topical glucocorticoid. {{Citation needed|date=July 2021}}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.<ref>{{cite journal | vauthors = Moriarty B, Hay R, Morris-Jones R |url=https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=The+diagnosis+and+management+of+tinea&btnG= |access-date=8 August 2024 |format=PDF | title = The diagnosis and management of tinea | journal = BMJ | volume = 345 | pages = e4380 | date = July 2012 | pmid = 22782730 | doi = 10.1136/bmj.e4380 | s2cid = 38106083 }}</ref>

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.<ref>{{cite journal | vauthors = Davies KJ |date=2006-03-01 |title=Study to determine the efficacy of Clotrimazole 1% cream for the treatment of onychomycosis in association with the mechanical reduction of the nail plate |url=https://www.sciencedirect.com/science/article/pii/S0958259205000829 |journal=The Foot |language=en |volume=16 |issue=1 |pages=19–22 |doi=10.1016/j.foot.2005.10.004 |issn=0958-2592}}</ref>

Topical and oral clotrimazole can be used in both adults and children.{{cn|date=December 2022}}

Additionally, clotrimazole may be used to treat the sickling of cells (related to ]).<ref>{{cite book | vauthors = Marieb EN, Hoehn K | title = Human Anatomy and Physiology | pages = 643 | location = Toronto | publisher = Pearson }}</ref><ref>{{cite web| vauthors = Rodgers G |title=Hydroxyurea and other disease-modifying therapies in sickle cell disease|url=http://www.uptodate.com/contents/hydroxyurea-and-other-disease-modifying-therapies-in-sickle-cell-disease?source=search_result&search=hydroxyurea&selectedTitle=1~87|publisher=UpToDate|access-date=14 April 2014|url-status=live|archive-url=https://web.archive.org/web/20140415042143/http://www.uptodate.com/contents/hydroxyurea-and-other-disease-modifying-therapies-in-sickle-cell-disease?source=search_result&search=hydroxyurea&selectedTitle=1~87|archive-date=15 April 2014}}</ref>

===Pregnancy===
Topical clotrimazole is categorized as ] B.<ref name=":0">{{cite journal | vauthors = Patel VM, Schwartz RA, Lambert WC | title = Topical antiviral and antifungal medications in pregnancy: a review of safety profiles | journal = Journal of the European Academy of Dermatology and Venereology | volume = 31 | issue = 9 | pages = 1440–1446 | date = September 2017 | pmid = 28449377 | doi = 10.1111/jdv.14297 | s2cid = 544751 }}</ref> Small amounts of clotrimazole may be absorbed systemically following topical and vaginal administration. However, topical clotrimazole is still considered safe to use to treat ]s in pregnant women and is a safer alternative to other antifungals.<ref name=":0"/><ref name="cdc.gov">{{cite web|title=Diseases Characterized by Vaginal Discharge|url=https://www.cdc.gov/std/treatment/2010/vaginal-discharge.htm|publisher=CDC|access-date=17 April 2014|url-status=dead|archive-url=https://web.archive.org/web/20140428171000/http://www.cdc.gov/sTD/treatment/2010/vaginal-discharge.htm|archive-date=28 April 2014}}</ref>

==Side effects==
]s of the oral formulation include itching, nausea, and vomiting. Less than 10% of patients using the oral formulation may have abnormal ]s. Side effects include rash, hives, blisters, burning, itching, peeling, redness, swelling, pain, or other signs of skin irritation.<ref name=AHFS2016/> For this reason, ]s should be monitored periodically when taking oral clotrimazole (troche). When used to treat vulvovaginal candidiasis (]), 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; ]; vulvar itching, soreness, edema, or discharge.<ref name="nlm.nih.gov"/><ref name="Clotrimazole Oral"/><ref name="Clotrimazole">{{cite web|title=Clotrimazole|url=http://www.drugbank.ca/drugs/DB00257|publisher=DrugBank|access-date=17 April 2014|url-status=live|archive-url=https://web.archive.org/web/20140417070045/http://www.drugbank.ca/drugs/DB00257|archive-date=17 April 2014}}</ref>

Clotrimazole creams and suppositories contain oil which may weaken latex ]s and ].<ref name="cdc.gov"/>

For topical formulations, should be used externally and should be discontinued if irritation or sensitivity develops at the site of administration.<ref>{{cite web|url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e03d9368-e1b4-4e37-87e4-3ee241916aed|title=DailyMed - CLOTRIMAZOLE ANTIFUNGAL- clotrimazole cream|website=dailymed.nlm.nih.gov|access-date=7 August 2019|archive-date=30 July 2020|archive-url=https://web.archive.org/web/20200730202932/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e03d9368-e1b4-4e37-87e4-3ee241916aed|url-status=live}}</ref>

==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 ] ], primarily ]. 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 before starting oral clotrimazole. Certain medications should not be taken with oral clotrimazole.<ref name="Clotrimazole"/>

==Pharmacology==

===Pharmacodynamics===
Clotrimazole is an ] derivative that works by inhibiting the growth of individual '']'' or fungal cells by altering the ] of the fungal ].<ref name="Clotrimazole Oral"/> The drug impairs the biosynthesis of ], a critical component of the fungal cell membrane, by inhibiting the P450 enzyme lanosterol 14-alpha demethylase.<ref>{{cite journal | vauthors = Crowley PD, Gallagher HC | title = Clotrimazole as a pharmaceutical: past, present and future | journal = Journal of Applied Microbiology | volume = 117 | issue = 3 | pages = 611–617 | date = September 2014 | pmid = 24863842 | doi = 10.1111/jam.12554 | url = https://ami-journals.onlinelibrary.wiley.com/doi/full/10.1111/jam.12554#:~:text=Clotrimazole%20targets%20the%20enzyme%20lanosterol,as%20terbinafine%2C%20target%20squalene%20epoxidase | access-date = 19 October 2023 | url-status = live | archive-url = https://web.archive.org/web/20240125065845/https://ami-journals.onlinelibrary.wiley.com/doi/full/10.1111/jam.12554#:~:text=Clotrimazole%20targets%20the%20enzyme%20lanosterol,as%20terbinafine%2C%20target%20squalene%20epoxidase | archive-date = 25 January 2024 }}</ref> Clotrimazole may ] or ].<ref name="AHFS2016"/>

==Sales volume==
] cream]]

Clotrimazole is available as a ],<ref name=AHFS2016/> and in 2016 Canesten brand Clotrimazole was one of the biggest-selling branded ] medications sold in Great Britain, with sales of £39.2 million.<ref>{{cite news|title=A breakdown of the over-the-counter medicines market in Britain in 2016|url=http://www.pharmaceutical-journal.com/20202662.article|access-date=29 May 2017|publisher=Pharmaceutical Journal|date=28 April 2017|archive-date=22 October 2019|archive-url=https://web.archive.org/web/20191022174148/https://www.pharmaceutical-journal.com/20202662.article|url-status=dead}} + (added 8 August 2024)</ref>
{{-}}

==References==
{{Reflist}}

{{Stomatological preparations}}
{{Antifungals}}
{{Gynecological anti-infectives and antiseptics}}
{{Transient receptor potential channel modulators}}
{{Xenobiotic-sensing receptor modulators}}
{{Portal bar | Medicine}}
{{Authority control}}

]
]
]
]
]
]
]
]
]
]
]
]
]