| 词条 | Miconazole |
| 释义 |
| Watchedfields = changed | verifiedrevid = 461740624 | IUPAC_name = (RS)-1-(2-(2,4-Dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl)-1H-imidazole | image = File:Miconazole.svg | width = 200px | image2 = Miconazole ball-and-stick.png | width2 = 200px | chirality = Racemic mixture | tradename = Desenex, Monistat, others | Drugs.com = {{drugs.com|monograph|miconazole-nitrate}} | MedlinePlus = a601203 | pregnancy_AU = A | pregnancy_AU_comment = (when used topically) | pregnancy_US = C | pregnancy_US_comment= (for topical use) | pregnancy_category = | legal_AU = S2 | legal_CA = | legal_UK = POM | legal_US = OTC | legal_AU_comment = Schedule 2 for topical formulations, schedule 3 for vaginal use and for oral candidiasis, otherwise schedule 4 | routes_of_administration = topical, vaginal, sublabial | bioavailability = | metabolism = | elimination_half-life = | excretion = | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 22916-47-8 | ATC_prefix = A01 | ATC_suffix = AB09 | ATC_supplemental = {{ATC|A07|AC01}} {{ATC|D01|AC02}} {{ATC|G01|AF04}} {{ATC|J02|AB01}} {{ATC|S02|AA13}} | PubChem = 4189 | IUPHAR_ligand = 2449 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB01110 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 4044 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 7NNO0D7S5M | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D00416 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 6923 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 91 | C=18 | H=14 | Cl=4 | N=2 | O=1 | molecular_weight = 416.127 g/mol | smiles = Clc1cc(Cl)ccc1C(Cn2ccnc2)OCc3ccc(Cl)cc3Cl | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = BYBLEWFAAKGYCD-UHFFFAOYSA-N }}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 used for ring worm of the body, groin (jock itch), and feet (athlete's foot).[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.[5] Miconazole is in the imidazole family of medications.[1] It works by decreasing the ability of fungi to make ergosterol, an important part of its cell membrane.[1] Miconazole was patented in 1968 and approved for medical use in 1971.[2] It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system.[3] The wholesale cost in the developing world is about 0.23 to US$0.60 for a 30 gram tube.[4] In the United States a course of treatment costs less than US$25.[5] Medical usesMiconazole is mainly used externally for the treatment of ringworm including jock itch and athlete's foot. 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 effectsUnlike 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|date=August 2014}}, some newer atypical antipsychotics, cyclosporin, and some statins used to treat hypercholesterolemia. Brand names and formulationsOral treatment: (brands: Daktarin in UK, Fungimin Oral Gel in Bangladesh )
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|date=May 2012}} 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)
Vaginal treatment: (brands: Miconazex, Monistat, Femizol or Gyno-Daktarin in UK)
PharmacologyMiconazole inhibits the fungal enzyme 14α-sterol demethylase, which reduces production of ergosterol.[7] In addition to its antifungal actions, miconazole, along with ketoconazole, is known to act as an antagonist of the glucocorticoid receptor.[8] RemyelinationMiconazole has been shown to promote remyelination of neurons in chronic progressive multiple sclerosis mouse models.[9] Physical propertiesThe solubilities of miconazole nitrate powder are 0.03% in water, 0.76% in ethanol and up to 4% in acetic acid.[10] Other usesMiconazole 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
References1. ^1 2 3 4 5 {{cite web|title=Miconazole Nitrate|url=https://www.drugs.com/monograph/miconazole-nitrate.html|publisher=The American Society of Health-System Pharmacists|accessdate=8 December 2016|deadurl=no|archiveurl=https://web.archive.org/web/20161221013013/https://www.drugs.com/monograph/miconazole-nitrate.html|archivedate=21 December 2016|df=}} 2. ^{{cite book|last1=Fischer|first1=Janos|last2=Ganellin|first2=C. Robin|title=Analogue-based Drug Discovery|date=2006|publisher=John Wiley & Sons|isbn=9783527607495|page=502|url=https://books.google.ca/books?id=FjKfqkaKkAAC&pg=PA502|language=en|deadurl=no|archiveurl=https://web.archive.org/web/20161220144314/https://books.google.ca/books?id=FjKfqkaKkAAC&pg=PA502|archivedate=2016-12-20|df=}} 3. ^{{cite web|title=WHO Model List of Essential Medicines (19th List)|url=http://www.who.int/medicines/publications/essentialmedicines/EML_2015_FINAL_amended_NOV2015.pdf?ua=1|website=World Health Organization|accessdate=8 December 2016|date=April 2015|deadurl=no|archiveurl=https://web.archive.org/web/20161213052708/http://www.who.int/medicines/publications/essentialmedicines/EML_2015_FINAL_amended_NOV2015.pdf?ua=1|archivedate=13 December 2016|df=}} 4. ^{{cite web|title=Miconazole Nitrate|url=http://mshpriceguide.org/en/single-drug-information/?DMFId=527&searchYear=2014|website=International Drug Price Indicator Guide|accessdate=8 December 2016|deadurl=no|archiveurl=https://web.archive.org/web/20170510104118/http://mshpriceguide.org/en/single-drug-information/?DMFId=527&searchYear=2014|archivedate=10 May 2017|df=}} 5. ^1 {{cite book|last1=Hamilton|first1=Richart|title=Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition|date=2015|publisher=Jones & Bartlett Learning|isbn=9781284057560|page=180}} 6. ^British National Formulary '45' March 2003 7. ^{{cite journal |last1=Becher |first1=R |last2=Wirsel |first2=SG |title=Fungal cytochrome P450 sterol 14α-demethylase (CYP51) and azole resistance in plant and human pathogens |journal=Applied Microbiology and Biotechnology |date=August 2012 |volume=95 |issue=4 |pages=825–40 |doi=10.1007/s00253-012-4195-9 |pmid=22684327}} 8. ^{{cite journal | vauthors = Duret C, Daujat-Chavanieu M, Pascussi JM, Pichard-Garcia L, Balaguer P, Fabre JM, Vilarem MJ, Maurel P, Gerbal-Chaloin S | 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 = Mol. Pharmacol. | volume = 70 | issue = 1 | pages = 329–39 | year = 2006 | pmid = 16608920 | doi = 10.1124/mol.105.022046 | url = http://www.hal.inserm.fr/inserm-00086861}} 9. ^{{Cite journal|title = Drug-based modulation of endogenous stem cells promotes functional remyelination in vivo|journal = Nature|date = 2015-01-01|volume = 522|issue = 7555|doi = 10.1038/nature14335|first = Fadi J.|last = Najm|first2 = Mayur|last2 = Madhavan|first3 = Anita|last3 = Zaremba|first4 = Elizabeth|last4 = Shick|first5 = Robert T.|last5 = Karl|first6 = Daniel C.|last6 = Factor|first7 = Tyler E.|last7 = Miller|first8 = Zachary S.|last8 = Nevin|first9 = Christopher|last9 = Kantor|pages=216–220|pmid=25896324|pmc=4528969}} 10. ^United States Patent 5461068 {{webarchive|url=https://web.archive.org/web/20140910102525/http://www.google.com/patents/US5461068 |date=2014-09-10 }} External linksMedical
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13 : 21-Hydroxylase inhibitors|Antiglucocorticoids|Aromatase inhibitors|Belgian inventions|CYP17A1 inhibitors|Ethers|Imidazole antifungals|Janssen Pharmaceutica|Chloroarenes|Lanosterol 14α-demethylase inhibitors|Otologicals|World Health Organization essential medicines|RTT |
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