Miconazole

Miconazole is used externally for the treatment of ringworm, jock itch, and athlete's foot. Internal application is used for oral candidiasis or vaginal thrush (yeast infection).

Miconazole is generally well tolerated. The oral gel can cause dry mouth, nausea and an unpleasant taste in about 1–10% of people. Anaphylactic reactions are rare. The drug prolongs the QT interval.

Miconazole is partly absorbed in the intestinal tract when used orally, as with the oral gel, and possibly when used vaginally.British National Formulary '45' March 2003 This can lead to increased concentrations of drugs that are metabolized by the liver enzymes CYP3A4 and CYP2C9, because miconazole inhibits these enzymes. Such interactions occur for example with anticoagulants of the warfarin type, phenytoin, some newer atypical antipsychotics, ciclosporin, and most statins used to treat hypercholesterolemia. These interactions are not relevant for miconazole that is applied to the skin.

Miconazole is contraindicated for people who use certain drugs that are metabolized by CYP3A4, for the reasons mentioned above:

• drugs that also prolong the QT interval because of potential problems with the heart rhythm
• ergot alkaloids
• statins
• triazolam and oral midazolam
• sulfonamides with a potential to cause hypoglycaemia (low blood sugar)

Miconazole inhibits the fungal enzyme 14α-sterol demethylase, resulting in a reduced production of ergosterol.{{cite journal | vauthors = Becher R, Wirsel SG | title = Fungal cytochrome P450 sterol 14α-demethylase (CYP51) and azole resistance in plant and human pathogens | journal = Applied Microbiology and Biotechnology | volume = 95 | issue = 4 | pages = 825–840 | date = August 2012 | pmid = 22684327 | doi = 10.1007/s00253-012-4195-9 | s2cid = 17688962 }} In addition to its antifungal actions, miconazole, similarly to ketoconazole, is known to act as an antagonist of the glucocorticoid receptor.{{cite journal | vauthors = Duret C, Daujat-Chavanieu M, Pascussi JM, Pichard-Garcia L, Balaguer P, Fabre JM, Vilarem MJ, Maurel P, Gerbal-Chaloin S | display-authors = 6 | title = Ketoconazole and miconazole are antagonists of the human glucocorticoid receptor: consequences on the expression and function of the constitutive androstane receptor and the pregnane X receptor | journal = Molecular Pharmacology | volume = 70 | issue = 1 | pages = 329–339 | date = July 2006 | pmid = 16608920 | doi = 10.1124/mol.105.022046 | s2cid = 21455699 }}

After application to the skin, miconazole can be measured in the skin for up to four days, but less than 1% is absorbed into the bloodstream. When applied to the oral mucosa (and possibly also for vaginal use), it is significantly absorbed. In the bloodstream, 88.2% are bound to plasma proteins and 10.6% to blood cells. The substance is partly metabolized via the liver enzyme CYP3A4 and mainly eliminated via the faeces.{{cite book|title=Austria-Codex| veditors = Haberfeld H |at=Daktarin 2%-Creme|publisher=Österreichischer Apothekerverlag|location=Vienna|year=2019|language=de}}{{cite book|title=Austria-Codex| veditors = Haberfeld H |at=Daktarin 2%-orales Gel|publisher=Österreichischer Apothekerverlag|location=Vienna|year=2020|language=de}}

The solubilities of miconazole nitrate powder are 0.03% in water, 0.76% in ethanol and up to 4% in acetic acid.{{cite patent | inventor = Thaler I, Strauss R | country = US | number = 5461068 | title = Imidazole derivative tincture and method of manufacture | assign1 = Current Assignee Corwood Laboratories Inc | assign2 = Bausch Health Companies Inc | gdate = 24 October 1995 | postscript = . }} Miconazole crystallises as colourless prisms in the monoclinic space group P2₁/c.{{cite journal | vauthors = Kaspiaruk H, Chęcińska L | title = A comparison of three crystalline forms of miconazole: solvent-free, ethanol monosolvate and hemihydrate | journal = Acta Crystallographica Section C | volume = 78 | issue = Pt 6 | pages = 343–350 | date = June 2022 | pmid = 35662134 | doi = 10.1107/S2053229622004909 | s2cid = 248839249 }}

Miconazole is also used in Ektachrome film developing in the final rinse of the Kodak E-6 process and similar Fuji CR-56 process,{{citation needed|date=June 2023}} replacing formaldehyde.{{cite web | title=Kodak Chemicals: Process E-6 Publication: Z-119 | website=Kodak | date=8 October 1999 | url=http://www.kodak.com/global/en/service/Zmanuals/z119.shtml | archive-url=https://web.archive.org/web/20070715005022/http://www.kodak.com/global/en/service/Zmanuals/z119.shtml | archive-date=15 July 2007 | url-status=dead | access-date=20 June 2023}}{{cite web | title=Kodak Chemicals: Q-LAB Process Control Handbook: Publication Z-6 | website=Kodak | date=1 November 2004 | url=http://www.kodak.com/global/en/service/Zmanuals/z6.shtml | archive-url=https://web.archive.org/web/20070207080023/http://www.kodak.com/global/en/service/Zmanuals/z6.shtml | archive-date=7 February 2007 | url-status=dead | access-date=20 June 2023}} Fuji Hunt also includes miconazole as a final rinse additive in their formulation of the C-41RA rapid access color negative developing process.{{citation needed|date=December 2022}}

File:Miconazol.jpg

Oral treatment: (brand names Daktarin in UK, Fungimin Oral Gel in Bangladesh):{{citation needed|date=December 2022}}

In 2010, the US Food and Drug Administration approved Oravig (miconazole) buccal tablets for the local treatment of oropharyngeal candidiasis, more commonly known as thrush, in adults and children age 16 and older.

External skin treatment (brand names Desenex and Zeasorb in US and Canada, Micatin, Monistat-Derm, Daktarin in India, UK, Australia, Belgium and the Philippines, Daktar in Norway, Fungidal in Bangladesh, Decocort in Malaysia){{citation needed|date=December 2022}} (Note that Desenex originally contained not miconazole, but rather the fungistatic agents, undecylenic acid and zinc undecylenate, which were in the foot powder developed by the US government for troops during WWII.{{Cite web |title=History |url=https://achh.army.mil/history/book-wwii-communicablediseasesv5-chapter7/ |access-date=2024-03-03 |website=achh.army.mil |language=en |archive-date=2024-03-03 |archive-url=https://web.archive.org/web/20240303214812/https://achh.army.mil/history/book-wwii-communicablediseasesv5-chapter7/ |url-status=live }})

Vaginal treatment (brand names Miconazex, Monistat, Femizol or Gyno-Daktarin in UK):{{citation needed|date=December 2022}}

{{clear}}

In Japan, Mochida Healthcare, a subsidiary of Mochida Pharmaceutical, produces a line of body soaps and shampoo under the brand name Collage (コラージュ) that contain miconazole nitrate as their main ingredient.{{Cite web|title=Mochida Pharmaceutical Co., list of product ingredients|url=https://hc.mochida.co.jp/products/ingredients/list.html|access-date=2024-08-21|website=hc.mochida.co.jp|language=ja}}

{{reflist}}

{{Stomatological preparations}}

{{Antidiarrheals, intestinal anti-inflammatory/anti-infective agents}}

{{Antifungals}}

{{Gynecological anti-infectives and antiseptics}}

{{Otologicals}}

{{Glucocorticoid receptor modulators}}

{{Portal bar | Medicine}}

{{Authority control}}

Category:21-Hydroxylase inhibitors

Category:Antiglucocorticoids

Category:Aromatase inhibitors

Category:Belgian inventions

Category:Chloroarenes

Category:CYP17A1 inhibitors

Category:CYP2C8 inhibitors

Category:CYP3A4 inhibitors

Category:Phenylethanolamine ethers

Category:Imidazole antifungals

Category:Lanosterol 14α-demethylase inhibitors

Category:Otologicals

Category:World Health Organization essential medicines

Category:Wikipedia medicine articles ready to translate

Category:General cytochrome P450 inhibitors