miconazole

ミコナゾール 　

WordNet

1. an antifungal agent usually administered in the form of a nitrate (trade name Monistat) (同)Monistat

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/01/19 02:07:40」(JST)

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Miconazole

Systematic (IUPAC) name
(RS)-1-(2-(2,4-Dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl)-1H-imidazole
Clinical data
Trade names	Desenex, Monistat, Zeasorb-AF
AHFS/Drugs.com	monograph
MedlinePlus	a601203
Pregnancy cat.	?
Legal status	POM (UK) OTC (US)
Routes	topical, vaginal
Pharmacokinetic data
Bioavailability	n/a
Metabolism	n/a
Half-life	n/a
Excretion	n/a
Identifiers
CAS number	22916-47-8 Y
ATC code	A01AB09 A07AC01 D01AC02 G01AF04 J02AB01 S02AA13
PubChem	CID 4189
IUPHAR ligand	2449
DrugBank	DB01110
ChemSpider	4044 Y
UNII	7NNO0D7S5M Y
KEGG	D00416 Y
ChEBI	CHEBI:6923 Y
ChEMBL	CHEMBL91 Y
Chemical data
Formula	C18H14Cl4N2O
Mol. mass	416.127 g/mol
SMILES Clc1ccc(c(Cl)c1)C(OCc2ccc(Cl)cc2Cl)Cn3ccnc3
InChI 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 Y Key:BYBLEWFAAKGYCD-UHFFFAOYSA-N Y
Y (what is this?)  (verify)

Miconazole is an imidazole antifungal agent, developed by Janssen Pharmaceutica, commonly applied topically to the skin or to mucus membranes to cure fungal infections. It works by inhibiting the synthesis of ergosterol, a critical component of fungal cell membranes. It can also be used against certain species of Leishmania protozoa which are a type of unicellular parasite that also contain ergosterol in their cell membranes. In addition to its antifungal and antiparasitic actions, it also has some limited antibacterial properties. It is marketed in various formulations under various brand names.

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.

Indications

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

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

Interactions are possible with anticoagulants, phenytoin, terbinafine, some newer atypical antipsychotics, ciclosporin and some statins used to treat hypercholesterolemia.

Brand names and formulations

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 (OPC), 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-AF in US and Canada, Micatin, Monistat-Derm, Daktarin in UK, Australia, Belgium and the Philippines, 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 mg or 100 mg
• Vaginal cream: 2% (7-day treatment); 4% (3-day treatment)
• Combination: 2% cream with either 100 mg or 200 mg.

Off-label use

Miconazole has recently gained some popularity as a hair-growth aid, although there is little evidence of its efficacy. Topical application of ketoconazole, a similar drug, has been shown to increase hair growth. However, oral administration of ketoconazole has also been shown to reduce hair growth in cases of hirsutism.

Physical properties

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

See also

• Antifungal medication
• Castor oil
• Clotrimazole
• Cremophor EL
• E-6 process
• Ektachrome
• Isoconazole

References

External links

Medical

• Micatin
• Miconazole (www.meds-help.com)
• Miconazole (National Institutes of Health)
• United States Patent 5461068 Imidazole derivative tincture and method of manufacture

Photographic

• Kodak process E6 Ektachrome (color transparency) processing manual Z-119
• Kodak process E6 Q-LAB processing manual Z-6 (more details than processing manual Z119 above)

UpToDate Contents

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English Journal

• Synthesis and Anti-Candida Potential of Certain Novel 1-[(3-Substituted-3-phenyl)propyl]-1H-imidazoles.

• Aboul-Enein MN, El-Azzouny AA, Attia MI, Saleh OA, Kansoh AL.SourceMedicinal and Pharmaceutical Chemistry Department, Pharmaceutical and Drug Industries Research Division, National Research Centre, Giza, Egypt. mnaboulenein@yahoo.com.
• Archiv der Pharmazie.Arch Pharm (Weinheim).2011 Oct 11. doi: 10.1002/ardp.201000224. [Epub ahead of print]
• The synthesis and anti-Candida activity of 1-[(3-aroyloxy-3-phenyl)propyl]-1H-imidazoles 5a-f and 1-[(3-alkyl/aralkyl/phenyl-3-phenyl)propan-3-ol]-1H-imidazoles 5g-j are reported. The influence of the ester formation and different substitutions on the anti-Candida activity of the alcohol 4 was inves
• PMID 21987482

• Comparison of two shampoos for the treatment of canine Malassezia dermatitis: a randomised controlled trial.

• Maynard L, Reme CA, Viaud S.SourceVIRBAC SA, 06511 Carros, France Clinique Veterinaire AQUIVET, ZAC Mermoz-Avenue de la Foret, 33320 Eysines, France.
• The Journal of small animal practice.J Small Anim Pract.2011 Oct 10. doi: 10.1111/j.1748-5827.2011.01124.x. [Epub ahead of print]
• Objectives: Two antimicrobial shampoos for treatment of canine Malassezia dermatitis (CMD) were compared in a prospective, randomised, single-blinded, field clinical trial. Methods: Sixty-seven dogs with pedal or generalised dermatitis associated with Malassezia overgrowth (MO) were treated with 3%
• PMID 21985533

Japanese Journal

• In Vitro Evaluation of Mucoadhesive Vaginal Tablets of Antifungal Drugs Prepared with Thiolated Polymer and Development of a New Dissolution Technique for Vaginal Formulations

• Baloglu Esra,Ay Senyıgıt Zeynep,Karavana Sinem Yaprak,Vetter Anja,Metın Dilek Yesim,Hilmioglu Polat Suleyha,Guneri Tamer,Bernkop-Schnurch Andreas
• CHEMICAL & PHARMACEUTICAL BULLETIN 59(8), 952-958, 2011
• … Econazole nitrate (EN) and miconazole nitrate (MN) were used as antifungal drugs to prepare the vaginal tablet formulations. …
• NAID 130000960925

• 漢方由来成分の配合を謳った中国製アトピー用クリームの医薬品成分の分析

• 平間 祐志,兼俊 明夫,長南 隆夫
• 北海道立衛生研究所報 (60), 33-37, 2010
• NAID 40018740138

Related Links

• Miconazole - Wikipedia, the free encyclopedia

Miconazole is an imidazole antifungal agent, developed by Janssen Pharmaceutica, commonly applied topically to the skin or to mucus membranes to cure fungal infections. It works by inhibiting the synthesis of ergosterol, a critical component ...

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