WordNet

any compound containing the nitrate group (such as a salt or ester of nitric acid)
treat with nitric acid, so as to change an organic compound into a nitrate; "nitroglycerin is obtained by nitrating glycerol"
an antifungal agent usually administered in the form of a nitrate (trade name Monistat) (同)Monistat

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硝酸塩 / 硝酸塩類化学肥料

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/01/19 07:18:44」(JST)

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Miconazole is an imidazole antifungal agent, developed by Janssen Pharmaceutica, commonly applied topically to the skin or to mucous 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 parasites that also contain ergosterol in their cell membranes. In addition to its antifungal and antiparasitic actions, it also has some 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.

It is on the World Health Organization's List of Essential Medicines, the most important medications needed in a basic health system.^[1]

Medical uses

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^[2]); this may lead to drug interactions.

Interactions are possible with anticoagulants, phenytoin, terbinafine,^{[citation needed]}, 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, 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

Off-label use

Miconazole has recently gained some popularity as a hair-growth aid,^[3] although little evidence indicates its efficacy. Topical application of ketoconazole, a similar drug, has been shown to increase hair growth.^[4] However, oral administration of ketoconazole has also been shown to reduce hair growth in cases of hirsutism.^[5]

Pharmacology

In addition to its antifungal actions, miconazole, along with ketoconazole, is known to act as an antagonist of the glucocorticoid receptor.^[6]

Remyelination

Miconazole has been shown to promote remyelination of neurons in chronic progressive multiple sclerosis mouse models.^[7]

Physical properties

The solubilities of miconazole nitrate powder are 0.03% in water 0.76% in ethanol and up to 4% in acetic acid.^[8]

References

^ "WHO Model List of EssentialMedicines" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014.
^ British National Formulary '45' March 2003
^ "Strange Beauty: Monistat Effectively Increases Hair Growth?". Black Girl With Long Hair. Retrieved 12 April 2012.
^ Ju, Jiang; Tsuboi, Ryoji; Kojima, Yuko; Ogawa, Hideoki (2005). "Topical application of ketoconazole stimulates hair growth in C3H/HeN mice". Journal of dermatology 32: 243–247.
^ S., Venturoli; O. Marescalchi; F. M. Colombo; S. Macrelli; B. Ravaioli; A. Bagnoli; R. Paradisi; C. Flamigni (April 1999). "A Prospective Randomized Trial Comparing Low Dose Flutamide, Finasteride, Ketoconazole, and Cyproterone Acetate-Estrogen Regimens in the Treatment of Hirsutism". The Journal of Clinical Endocrinology and Metabolism 84 (4): 1304–1310. doi:10.1210/jc.84.4.1304. Retrieved 12 April 2012.
^ 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.
^ 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). doi:10.1038/nature14335.
^ United States Patent 5461068

External links

Medical

Micatin
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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1. カンジダ外陰腟炎：治療candida vulvovaginitis treatment [show details]
…fluconazole but is highly susceptible to clotrimazole, miconazole, and terconazole. For pregnant women, we suggest a topical imidazole (clotrimazole, miconazole) vaginally for seven days rather than a nystatin …
2. おむつ皮膚炎diaper dermatitis [show details]
…suppression and iatrogenic Cushing syndrome . Antifungal agents such as nystatin, clotrimazole, miconazole, ketoconazole, and sertaconazole are effective topical therapies for diaper dermatitis complicated…
3. 紅色陰癬erythrasma [show details]
…therapies that included small numbers of patients with erythrasma, treatment with oxiconazole, miconazole, tioconazole, or econazole twice daily for 7 to 60 days cleared more than 90 percent of erythrasma…
4. 自由生活性アメーバおよびプロトテカfree living amebas and prototheca [show details]
…rifampin has also been described. In one case, intrathecal administration of amphotericin B and miconazole was used . The use of miltefosine for treatment of PAM has been extrapolated from favorable clinical…
5. 新生児におけるカンジダ感染の予防prevention of candida infection in neonates [show details]
…statistically significant (3 versus 6 percent; risk ratio 0.53, 95% CI 0.19-1.52) . Nystatin and miconazole are local antifungal agents without systemic distribution because they are not well absorbed from…

English Journal

Nystatin and miconazole: pharmacological and clinical evidence regarding interactions with warfarin.

Pemberton MN1.
Oral diseases.Oral Dis.2016 Nov;22(8):761-765. doi: 10.1111/odi.12541. Epub 2016 Aug 8.
OBJECTIVE: A retrospective case series published in 2012 concluded that miconazole and nystatin used as topical antifungal drugs appear to interact equally strongly with warfarin. If confirmed, this finding has significant implications for clinical practice. This study evaluates the evidence.MATERIA
PMID 27416928

Modeling dermatophytosis in reconstructed human epidermis: A new tool to study infection mechanisms and to test antifungal agents.

Faway É1, Cambier L2, Mignon B2, Poumay Y3, Lambert de Rouvroit C1.
Medical mycology.Med Mycol.2016 Oct 19. pii: myw111. [Epub ahead of print]
Dermatophytosis is a superficial fungal infection of keratinized structures that exhibits an increasing prevalence in humans and is thus requesting novel prophylactic strategies and therapies. However, precise mechanisms used by dermatophytes to adhere at the surface of the human epidermis and invad
PMID 27760830

New denture adhesive containing miconazole nitrate polymeric microparticles: Antifungal, adhesive force and toxicity properties.

Cartagena AF1, Esmerino LA2, Polak-Junior R3, Olivieri Parreiras S4, Domingos Michél M3, Farago PV2, Campanha NH4.
Dental materials : official publication of the Academy of Dental Materials.Dent Mater.2016 Oct 10. pii: S0109-5641(16)30487-0. doi: 10.1016/j.dental.2016.09.039. [Epub ahead of print]
OBJECTIVE: The purpose of this study was to develop a new oral drug delivery system by incorporating polymeric miconazole nitrate (MN) microparticles on an experimental antifungal denture adhesive (DA).METHODS: Spray drying Eudragit L-100 (E) and Gantrez MS-955 (G) MN-microparticles were incorporate
PMID 27745775

Japanese Journal

フケ症に対するミコナゾール硝酸塩配合リンスの有用性の検討 : 基剤を対照とした二重盲検比較試験

清佳浩,小林めぐみ,早出恵里
Medical mycology journal = / 日本医真菌学会 [編] 52(3), 229-237, 2011-07-30
… double-blind, comparative study was performed on the usefulness of rinse containing miconazole nitrate(COFRM)compared to rinse without the reagent for the treatment of dandruff, when together with shampoo containing miconazole nitrate(COF). This study showed that both COFR and COFRM had about 80% utility. On the other hand, though it was not significant, enhanced improvement of itching by COFRM compared to COFR was detected 2 weeks after …
NAID 10029466295

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 Senyigit Zeynep,Karavana Sinem Yaprak [他],Vetter Anja,Metın Dilek Yesim,Hilmioglu Polat Suleyha,Guneri Tamer,Bernkop-Schnurch Andreas
Chemical and 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

症例 Acute Generalized Exanthematous Pustulosis様の病態を呈した硝酸ミコナゾールによる接触皮膚炎症候群の1例

攝田麻里,穐山雄一郎,小村一浩 [他]
皮膚科の臨床 52(2), 211-215, 2010-02-00
NAID 40016986273

Related Pictures

★リンクテーブル★

リンク元	「ミコナゾール」
関連記事	「nitrate」

「ミコナゾール」

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; 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 oral and topical treatment.;
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;
Routes of; administration	topical, vaginal, sublabial, oral
Pharmacokinetic data
Bioavailability	n/a
Metabolism	n/a
Biological half-life	n/a
Excretion	n/a
Identifiers
CAS Number	22916-47-8
ATC code	A01AB09 A07AC01 D01AC02 G01AF04 J02AB01 S02AA13
PubChem	CID: 4189
IUPHAR/BPS	2449
DrugBank	DB01110
ChemSpider	4044
UNII	7NNO0D7S5M
KEGG	D00416
ChEBI	CHEBI:6923
ChEMBL	CHEMBL91
Chemical data
Formula	C18H14Cl4N2O
Molecular 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 ; Key:BYBLEWFAAKGYCD-UHFFFAOYSA-N ;
(verify)

　　[★]

英: miconazole, MCZ
化: 硝酸ミコナゾール miconazole nitrate
商: アムリード、サラシルト、フロリードD、フロリードF、フロリードゲル、フロリード腟坐剤
関: 抗真菌薬、寄生性皮ふ疾患用剤

「nitrate」

　　[★]

硝酸、(化合物)硝酸塩、硝酸薬、ナイトレート、ニトロ化する

関: HNO3、nitration、nitric acid

[1] "WHO Model List of EssentialMedicines" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014.

[2] British National Formulary '45' March 2003

[3] "Strange Beauty: Monistat Effectively Increases Hair Growth?". Black Girl With Long Hair. Retrieved 12 April 2012.

[4] Ju, Jiang; Tsuboi, Ryoji; Kojima, Yuko; Ogawa, Hideoki (2005). "Topical application of ketoconazole stimulates hair growth in C3H/HeN mice". Journal of dermatology 32: 243–247.

[5] S., Venturoli; O. Marescalchi; F. M. Colombo; S. Macrelli; B. Ravaioli; A. Bagnoli; R. Paradisi; C. Flamigni (April 1999). "A Prospective Randomized Trial Comparing Low Dose Flutamide, Finasteride, Ketoconazole, and Cyproterone Acetate-Estrogen Regimens in the Treatment of Hirsutism". The Journal of Clinical Endocrinology and Metabolism 84 (4): 1304–1310. doi:10.1210/jc.84.4.1304. Retrieved 12 April 2012.

[pmid16608920-6] 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.

[7] 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). doi:10.1038/nature14335.

[8] United States Patent 5461068

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案内

miconazole nitrate