Miconazole

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Miconazole
Miconazole.svg
Miconazole ball-and-stick.png
Clinical data
Trade names Desenex, Monistat, others
AHFS/Drugs.com Monograph
MedlinePlus a601203
Pregnancy
category
  • AU: A
  • US: C (Risk not ruled out)
  • In Australia, it is category A when used topically. In the US, the pregnancy category is C for topical use.
Routes of
administration
topical, vaginal, sublabial
ATC code A01AB09 (WHO) A07AC01 (WHO) D01AC02 (WHO) G01AF04 (WHO) J02AB01 (WHO) S02AA13 (WHO)
Legal status
Legal status
  • AU: S2 (Pharmacy only)
  • UK: POM (Prescription only)
  • US: OTC
  • Schedule 2 in Australia for topical formulations, schedule 3 (Aus) for vaginal use and for oral candidiasis, otherwise schedule 4 in Australia
Identifiers
CAS Number 22916-47-8 YesY
PubChem (CID) 4189
IUPHAR/BPS 2449
DrugBank DB01110 YesY
ChemSpider 4044 YesY
UNII 7NNO0D7S5M YesY
KEGG D00416 YesY
ChEBI CHEBI:6923 YesY
ChEMBL CHEMBL91 YesY
ECHA InfoCard 100.041.188
Chemical and physical data
Formula C18H14Cl4N2O
Molar mass 416.127 g/mol
3D model (Jmol) Interactive image
Chirality Racemic mixture
  (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.[1] It is applied to the skin or vagina as a cream or ointment.[1]

Common side effects include itchiness or irritation of the area in which it was applied.[1] Use in pregnancy is believed to be safe for the baby.[2] Miconazole is in the imidazole family of medications. It works by decreasing the ability of fungi to make ergosterol, an important part its cell membrane.[1]

Miconazole was patented in 1968 and approved for medical use in 1971.[3] It is on the World Health Organization's List of Essential Medicines, the most important medications needed in a basic health system.[4] The wholesale cost in the developing world is about 0.23 to 0.60 USD for a 30 gm tube.[5] In the United States a course of treatment costs less than 25 USD.[2]

Medical uses[edit]

Miconazole is mainly used externally for the treatment of athlete's foot, ringworm, and jock itch. Internal application is used for oral or vaginal thrush (yeast infection). The oral gel may also be used for the lip disorder angular cheilitis.

In the UK, miconazole may be used to treat neonatal oral thrush, while the alternative nystatin is only licensed for patients over the age of one month, but drug interactions are possible.

Side effects[edit]

Unlike nystatin, some miconazole is absorbed by the intestinal tract when used orally (and possibly if used vaginally[6]); this may lead to drug interactions.

Interactions are possible with anticoagulants, phenytoin, terbinafine,[citation needed], some newer atypical antipsychotics, cyclosporin, and some statins used to treat hypercholesterolemia.

Brand names and formulations[edit]

Vaginal miconazole 20 mg/g - Brazil

Oral treatment: (brands: Daktarin in UK)

  • Oral gel 24 mg/ml (20 mg/g)
  • Oravig 50 mg once daily buccal tablet:

In 2010, the U.S. Food and Drug Administration approved Oravig (miconazole) buccal tablets once daily for the local treatment of oropharyngeal candidiasis, more commonly known as thrush, in adults and children age 16 and older. Oravig is the only local, oral prescription formulation of miconazole approved for this use in the U.S.[citation needed]

External skin treatment: (brands: 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)

  • Topical cream: 2%
  • Combination: hydrocortisone/miconazole cream with 1% and 2%, respectively (Daktacort in UK, Daktodor in Greece)
  • Dusting powder: 2% powder with chlorhexidine hydrochloride (mycoDust)

Vaginal treatment: (brands: Miconazex, Monistat, Femizol or Gyno-Daktarin in UK)

  • Pessaries: 200 or 100 mg
  • Vaginal cream: 2% (7-day treatment), 4% (3-day treatment)
  • Combination: 2% cream with either 100 or 200 mg

Pharmacology[edit]

In addition to its antifungal actions, miconazole, along with ketoconazole, is known to act as an antagonist of the glucocorticoid receptor.[7]

Remyelination[edit]

Miconazole has been shown to promote remyelination of neurons in chronic progressive multiple sclerosis mouse models.[8]

Physical properties[edit]

The solubilities of miconazole nitrate powder are 0.03% in water 0.76% in ethanol and up to 4% in acetic acid.[9]

Other uses[edit]

Miconazole is also used in Ektachrome film developing in the final rinse of the Kodak E-6 process and similar Fuji CR-56 process, replacing formaldehyde. Fuji Hunt also includes miconazole as a final rinse additive in their formulation of the C-41RA rapid access color negative developing process.

See also[edit]

References[edit]

  1. ^ a b c d "Miconazole Nitrate". The American Society of Health-System Pharmacists. Retrieved 8 December 2016. 
  2. ^ a b Hamilton, Richart (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 180. ISBN 9781284057560. 
  3. ^ Fischer, Janos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 502. ISBN 9783527607495. 
  4. ^ "WHO Model List of EssentialMedicines" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014. 
  5. ^ "Miconazole Nitrate". International Drug Price Indicator Guide. Retrieved 8 December 2016. 
  6. ^ British National Formulary '45' March 2003
  7. ^ Duret C, Daujat-Chavanieu M, Pascussi JM, Pichard-Garcia L, Balaguer P, Fabre JM, Vilarem MJ, Maurel P, Gerbal-Chaloin S (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". Mol. Pharmacol. 70 (1): 329–39. doi:10.1124/mol.105.022046. PMID 16608920. 
  8. ^ Najm, Fadi J.; Madhavan, Mayur; Zaremba, Anita; Shick, Elizabeth; Karl, Robert T.; Factor, Daniel C.; Miller, Tyler E.; Nevin, Zachary S.; Kantor, Christopher (2015-01-01). "Drug-based modulation of endogenous stem cells promotes functional remyelination in vivo". Nature. 522 (7555): 216–220. doi:10.1038/nature14335. 
  9. ^ United States Patent 5461068

External links[edit]

Medical[edit]

Photographic[edit]