Miconazole

Last updated

Miconazole
Miconazole.svg
Miconazole ball-and-stick.png
Clinical data
Trade names Monistat, others
AHFS/Drugs.com Monograph
MedlinePlus a601203
License data
Routes of
administration 		Topical, vaginal, sublabial
ATC code
Legal status
Legal status
  • AU: S2 (Pharmacy medicine)Schedule 2 for topical formulations, schedule 3 for vaginal use and for oral candidiasis, otherwise schedule 4[ citation needed ]
  • UK: POM (Prescription only)
  • US: OTC / Rx-only [1]
Pharmacokinetic data
Bioavailability <1% after application to the skin
Protein binding 88.2%
Metabolism CYP3A4
Elimination half-life 20–25 hrs
Excretion Mainly feces
Identifiers
  • (RS)-1-(2-(2,4-Dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl)-1H-imidazole
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.041.188 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C18H14Cl4N2O
Molar mass 416.12 g·mol−1
3D model (JSmol)
Chirality Racemic mixture
  • Clc1cc(Cl)ccc1C(Cn2ccnc2)OCc3ccc(Cl)cc3Cl
  • InChI=1S/C18H14Cl4N2O/c19-13-2-1-12(16(21)7-13)10-25-18(9-24-6-5-23-11-24)15-4-3-14(20)8-17(15)22/h1-8,11,18H,9-10H2 Yes check.svgY
  • Key:BYBLEWFAAKGYCD-UHFFFAOYSA-N Yes check.svgY
   (verify)

Miconazole, sold under the brand name Monistat among others, is an antifungal medication used to treat ring worm, pityriasis versicolor, and yeast infections of the skin or vagina. [2] It is used for ring worm of the body, groin (jock itch), and feet (athlete's foot). [2] It is applied to the skin or vagina as a cream or ointment. [2] [3]

Contents

Common side effects include itchiness or irritation of the area in which it was applied. [2] Use in pregnancy is believed to be safe for the baby. [4] Miconazole is in the imidazole family of medications. [2] It works by decreasing the ability of fungi to make ergosterol, an important part of their cell membrane. [2]

Miconazole was patented in 1968 and approved for medical use in 1971. [5] It is on the World Health Organization's List of Essential Medicines. [6] It is available as a generic medication. [2]

Medical uses

Miconazole is used externally for the treatment of ringworm, jock itch, and athlete's foot. [2] Internal application is used for oral candidiasis or vaginal thrush (yeast infection). [2]

Side effects

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. [7] [8]

Interactions

Miconazole is partly absorbed in the intestinal tract when used orally, as with the oral gel, and possibly when used vaginally. [9] 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. [8] These interactions are not relevant for miconazole that is applied to the skin. [8]

Contraindications

Miconazole is contraindicated for people who use certain drugs that are metabolized by CYP3A4, for the reasons mentioned above: [8]

Pharmacology

Mechanism of action

Miconazole inhibits the fungal enzyme 14α-sterol demethylase, resulting in a reduced production of ergosterol. [10] In addition to its antifungal actions, miconazole, similarly to ketoconazole, is known to act as an antagonist of the glucocorticoid receptor. [11]

Pharmacokinetics

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 [9] ), 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. [7] [8]

Chemistry

The solubilities of miconazole nitrate powder are 0.03% in water, 0.76% in ethanol and up to 4% in acetic acid. [12] Miconazole crystallises as colourless prisms in the monoclinic space group P21/c. [13]

Other uses

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 ] replacing formaldehyde. [14] [15] 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 ]

Brands and formulations

Vaginal miconazole 20 mg/g - Brazil Miconazol.jpg
Vaginal miconazole 20 mg/g - Brazil

Oral treatment: (brand names Daktarin in UK, Fungimin Oral Gel in Bangladesh):[ citation needed ]

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. [1]

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 ] (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. [16] )

Vaginal treatment (brand names Miconazex, Monistat, Femizol or Gyno-Daktarin in UK):[ citation needed ]

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. [17]

Related Research Articles

<span class="mw-page-title-main">Antifungal</span> Pharmaceutical fungicide or fungistatic used to treat and prevent mycosis

An antifungal medication, also known as an antimycotic medication, is a pharmaceutical fungicide or fungistatic used to treat and prevent mycosis such as athlete's foot, ringworm, candidiasis (thrush), serious systemic infections such as cryptococcal meningitis, and others. Such drugs are usually obtained by a doctor's prescription, but a few are available over the counter (OTC). The evolution of antifungal resistance is a growing threat to health globally.

<span class="mw-page-title-main">Nystatin</span> Antifungal medication

Nystatin, sold under the brand name Mycostatin among others, is an antifungal medication. It is used to treat Candida infections of the skin including diaper rash, thrush, esophageal candidiasis, and vaginal yeast infections. It may also be used to prevent candidiasis in those who are at high risk. Nystatin may be used by mouth, in the vagina, or applied to the skin.

<span class="mw-page-title-main">Ketoconazole</span> Antifungal chemical compound

Ketoconazole, sold under the brand name Nizoral among others, is an antiandrogen, antifungal, and antiglucocorticoid medication used to treat a number of fungal infections. Applied to the skin it is used for fungal skin infections such as tinea, cutaneous candidiasis, pityriasis versicolor, dandruff, and seborrheic dermatitis. Taken by mouth it is a less preferred option and only recommended for severe infections when other agents cannot be used. Other uses include treatment of excessive male-patterned hair growth in women and Cushing's syndrome.

<span class="mw-page-title-main">Fluconazole</span> Antifungal medication

Fluconazole is an antifungal medication used for a number of fungal infections. This includes candidiasis, blastomycosis, coccidioidomycosis, cryptococcosis, histoplasmosis, dermatophytosis, and tinea versicolor. It is also used to prevent candidiasis in those who are at high risk such as following organ transplantation, low birth weight babies, and those with low blood neutrophil counts. It is given either by mouth or by injection into a vein.

<span class="mw-page-title-main">Triamcinolone</span> Steroid medication

Triamcinolone is a glucocorticoid used to treat certain skin diseases, allergies, and rheumatic disorders among others. It is also used to prevent worsening of asthma and COPD. It can be taken in various ways including by mouth, injection into a muscle, and inhalation.

<span class="mw-page-title-main">Eletriptan</span> Chemical compound

Eletriptan, sold under the brand name Relpax and used in the form of eletriptan hydrobromide, is a second-generation triptan medication intended for treatment of migraine headaches. It is used as an abortive medication, blocking a migraine attack which is already in progress. Eletriptan is marketed and manufactured by Pfizer Inc.

<span class="mw-page-title-main">Sertaconazole</span> Antifungal medication

Sertaconazole, sold under the brand name Ertaczo among others, is an antifungal medication of the Benzothiophene class. It is available as a cream to treat skin infections such as athlete's foot.

<span class="mw-page-title-main">Posaconazole</span> Pharmaceutical drug

Posaconazole, sold under the brand name Noxafil among others, is a triazole antifungal medication.

<span class="mw-page-title-main">Phenprocoumon</span> Drug

Phenprocoumon is a long-acting blood thinner drug to be taken by mouth, and a coumarin derivative. It acts as a vitamin K antagonist and inhibits blood clotting (coagulation) by blocking synthesis of coagulation factors II, VII, IX and X. It is used for the prophylaxis and treatment of thromboembolic disorders such as heart attacks and pulmonary (lung) embolism. The most common adverse effect is bleeding. The drug interacts with a large number of other medications, including aspirin and St John's Wort. It is the standard coumarin used in Germany, Austria, and other European countries.

<span class="mw-page-title-main">Nisoldipine</span> Antihypertensive drug of the calcium channel blocker class

Nisoldipine is a pharmaceutical drug used for the treatment of chronic angina pectoris and hypertension. It is a calcium channel blocker of the dihydropyridine class. It is sold in the United States under the proprietary name Sular. Nisoldipine has tropism for cardiac blood vessels.

<span class="mw-page-title-main">Silodosin</span> Chemical compound

Silodosin, sold under the brand name Urief among others, is a medication for the symptomatic treatment of benign prostatic hyperplasia. It acts as an alpha-1 adrenergic receptor antagonist.

<span class="mw-page-title-main">Fenticonazole</span> Chemical compound

Fenticonazole is an imidazole antifungal drug, used locally as the nitrate in the treatment of vulvovaginal candidiasis. It is active against a range of organisms including dermatophyte pathogens, Malassezia furfur, and Candida albicans. Fenticonazole has also been shown to exhibit antibacterial action, with a spectrum of activity that includes bacteria commonly associated with superinfected fungal skin and vaginal infections, and antiparasitic action against the protozoan Trichomonas vaginalis.

<span class="mw-page-title-main">Sterol 14-demethylase</span> Class of enzymes

In enzymology, a sterol 14-demethylase (EC 1.14.13.70) is an enzyme of the cytochrome P450 (CYP) superfamily. It is any member of the CYP51 family. It catalyzes a chemical reaction such as:

<span class="mw-page-title-main">Clotrimazole</span> Chemical compound

Clotrimazole, sold under the brand name Lotrimin, among others, is an antifungal medication. 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. It can be taken by mouth or applied as a cream to the skin or in the vagina.

<span class="mw-page-title-main">Isavuconazonium</span> Chemical compound

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<span class="mw-page-title-main">Prochloraz</span> Chemical compound

Prochloraz, brand name Sportak, is an imidazole fungicide that was introduced in 1978 and is widely used in Europe, Australia, Asia, and South America within gardening and agriculture to control the growth of fungi. It is not registered for use in the United States. Similarly to other azole fungicides, prochloraz is an inhibitor of the enzyme lanosterol 14α-demethylase (CYP51A1), which is necessary for the production of ergosterol – an essential component of the fungal cell membrane – from lanosterol. The agent is a broad-spectrum, protective and curative fungicide, effective against Alternaria spp., Botrytis spp., Erysiphe spp., Helminthosporium spp., Fusarium spp., Pseudocerosporella spp., Pyrenophora spp., Rhynchosporium spp., and Septoria spp.

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References

  1. 1 2 "Oravig- miconazole tablet". DailyMed. 1 January 2022. Archived from the original on 14 August 2022. Retrieved 20 June 2023.
  2. 1 2 3 4 5 6 7 8 9 "Miconazole Nitrate". The American Society of Health-System Pharmacists. Archived from the original on 21 December 2016. Retrieved 8 December 2016.
  3. ↑ "Miconazole Monograph for Professionals". Drugs.com. 22 July 2022. Archived from the original on 21 September 2022. Retrieved 20 June 2023.
  4. ↑ Hamilton R (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 180. ISBN   9781284057560.
  5. ↑ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 502. ISBN   9783527607495. Archived from the original on 20 December 2016.
  6. ↑ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl: 10665/371090 . WHO/MHP/HPS/EML/2023.02.
  7. 1 2 Haberfeld H, ed. (2019). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag. Daktarin 2%-Creme.
  8. 1 2 3 4 5 Haberfeld H, ed. (2020). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag. Daktarin 2%-orales Gel.
  9. 1 2 British National Formulary '45' March 2003
  10. ↑ Becher R, Wirsel SG (August 2012). "Fungal cytochrome P450 sterol 14α-demethylase (CYP51) and azole resistance in plant and human pathogens". Applied Microbiology and Biotechnology. 95 (4): 825–840. doi:10.1007/s00253-012-4195-9. PMID   22684327. S2CID   17688962.
  11. ↑ Duret C, Daujat-Chavanieu M, Pascussi JM, Pichard-Garcia L, Balaguer P, Fabre JM, et al. (July 2006). "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". Molecular Pharmacology. 70 (1): 329–339. doi:10.1124/mol.105.022046. PMID   16608920. S2CID   21455699.{{cite journal}}: CS1 maint: overridden setting (link)
  12. ↑ US 5461068,Thaler I, Strauss R,"Imidazole derivative tincture and method of manufacture",issued 24 October 1995, assigned to Current Assignee Corwood Laboratories Incand Bausch Health Companies Inc.
  13. ↑ Kaspiaruk H, Chęcińska L (June 2022). "A comparison of three crystalline forms of miconazole: solvent-free, ethanol monosolvate and hemihydrate". Acta Crystallographica Section C. 78 (Pt 6): 343–350. doi:10.1107/S2053229622004909. PMID   35662134. S2CID   248839249.
  14. ↑ "Kodak Chemicals: Process E-6 Publication: Z-119". Kodak. 8 October 1999. Archived from the original on 15 July 2007. Retrieved 20 June 2023.
  15. ↑ "Kodak Chemicals: Q-LAB Process Control Handbook: Publication Z-6". Kodak. 1 November 2004. Archived from the original on 7 February 2007. Retrieved 20 June 2023.
  16. ↑ "History". achh.army.mil. Archived from the original on 3 March 2024. Retrieved 3 March 2024.
  17. ↑ "Mochida Pharmaceutical Co., list of product ingredients". hc.mochida.co.jp (in jp). Retrieved 21 August 2024.{{cite web}}: CS1 maint: unrecognized language (link)
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