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M3512 Sigma

(±)-Miconazole nitrate salt

imidazole antibiotic

Synonym: 1-(2,4-Dichloro-β-[(2,4-dichlorobenzyl)oxy]phenethyl)imidazole

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Description

Application

Miconazole is an imidazole antifungal agent that is used topically and by intravenous infusion. It is used to inhibit cytochrome P450 1 and to study automated luminescence-based cytochrome P450 profiling2.

Biochem/physiol Actions

Miconazole interacts with 14-α demethylase, a cytochrome P-450 enzyme necessary for ergosterol biosynthesis. The inhibition of ergosterol results in increased cellular permeability causing leakage of cellular contents. Miconazole may also inhibit endogenous respiration, interact with phospholipids in the cell membrane, inhibit the transformation of yeasts to mycelial forms, inhibit purine uptake, and interfere with triglyceride and phospholipid biosynthesis.

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(±)-Miconazole nitrate salt

pharamaceutical secondard standard: traceable to UPS, PhEur and BP

M1880000Miconazole

European Pharmacopoeia (EP) Reference Standard

Miconazole nitrate

United States Pharmacopeia (USP) Reference Standard

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
Hazard Codes (Europe) 
Xn
Risk Statements (Europe) 
Safety Statements (Europe) 
36/37
WGK Germany 
3
RTECS 
NI4771000

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Peer-Reviewed Papers

References

Set your institution to view full text papers.

1. Carotenoid Biosynthesis in the Primitive Red Alga Cyanidioschyzon merolae Francis X. Cunningham, Jr., Hansel Lee, et al. Eukaryotic Cell 6, 533-545, (2007)

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2. Automated Luminescence-Based Cytochrome P450 Profiling Using a Simple, Elegant Robotic Platform Brad Larson, Peter Banks, et al. J. Assoc. Lab. Autom. 16, 47-55, (2011)

Identification and characterization of mefloquine efficacy against JC virus in vitro. Margot Brickelmaier et al Antimicrob. Agents Chemother. 53, 1840-9, (2009)

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Fungicidal drugs induce a common oxidative-damage cellular death pathway. Belenky P, Camacho D, and Collins JJ Cell Rep. 3(2), 350-8, (2013)

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A high-content assay to identify small-molecule modulators of a cancer stem cell population in luminal breast cancer. Yoo BH, Axlund SD, Kabos P, et al. J. Biomol. Screen. 17(9), 1211-20, (2012)

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Anti-Candida drugs--the biochemical basis for their activity. Vanden Bossche, H., et al. Crit. Rev. Microbiol 15, 57-72, (1987)

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The benefits of combination therapy in dermatomycoses. Veraldi S Mycoses 56 Suppl 1, 1-2, (2013)

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Double-blind study with topical Isoconazole and Terbinafine for the treatment of one patient with bilateral Tinea nigra plantaris and suggestions for new differential diagnosis. Rossetto AL, Cruz RC, and Haddad Junior V Rev. Inst. Med. Trop. Sao Paulo 55(2), 125-8, (2013)

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Comparison of four reading methods of broth microdilution based on the clinical and laboratory standards institute M27-A3 method for Candida spp. Morishige H, Mano Y, Oguri T, et al. Jpn. J. Antibiot. 65(5), 335-47, (2012)

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[Drug interactions between coumarin derivatives and antimycotics: also with topical antifungal agents]. Jessurun NT and van Puijenbroek EP Ned. Tijdschr. Geneeskd. 157(4), A5317, (2013)

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In vitro antifungal activity of two tissue conditioners combined with nystatin, miconazole and fluconazole against Candida albicans. Chopde N, Pharande A, Khade MN, et al. J. Contemp. Dent. Pract. 13(5), 695-8, (2012)

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[Generalized cutaneous candidiasis in newborn at term]. El Ahmed HH, Cañadas-De la Fuente GA, Fernández-Castillo R, et al. Biomedica. 32(2), 170-3, (2012)

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Isoconazole nitrate vs isoconazole nitrate and diflucortolone valerate in the treatment of tinea inguinalis: results of a multicenter retrospective study. Veraldi S, Persico MC, and Schianchi R Journal. of. Drugs in. Dermatology. 11(11), e70-3, (2012)

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Oral chronic hyperplastic candidiasis associated with juvenile dermatomyositis. Ferreira Dde C, Dos Santos KR, and Herdy GV Rev. Soc. Bras. Med. Trop. 45(4), 540, (2012)

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Preparation and characterization of biomimetic nanoparticles for drug delivery. Carmona-Ribeiro AM Methods Mol. Biol. 906, 283-94, (2012)

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Synthesis and antimicrobial evaluation of new benzofuran derivatives. Xizhen Jiang et al Eur. J. Med. Chem. 46, 3526-30, (2011)

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Miconazole: a historical perspective. Fothergill, A.W. Expert Rev. Anti. Infect. Ther. 4, 171-5, (2006)

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Formulation and drying of miconazole and itraconazole nanosuspensions. Cerdeira AM, Mazzotti M, and Gander B Int. J. Pharm. 443(1-2), 209-20, (2013)

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Antimicrobial and cytotoxic arylazoenamines. Part III: antiviral activity of selected classes of arylazoenamines. Michele Tonelli et al Bioorg. Med. Chem. 16, 8447-65, (2008)

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Antifungal agents from Pseudallescheria boydii SNB-CN73 isolated from a Nasutitermes sp. termite. Nirma C, Eparvier V, and Stien D J. Nat. Prod. 76(5), 988-91, (2013)

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Evaluation of the antifungal activity of Zataria multiflora, Geranium herbarium, and Eucalyptus camaldolensis essential oils on Saprolegnia parasitica-infected rainbow trout (Oncorhynchus mykiss) eggs. Khosravi AR, Shokri H, Sharifrohani M, et al. Foodborne Pathog. Dis. 9(7), 674-9, (2012)

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Effective microPET imaging of brain 5-HT(1A) receptors in rats with [(18) F]MeFWAY by suppression of radioligand defluorination. Choi JY, Kim CH, Jeon TJ, et al. Synapse 66(12), 1015-23, (2012)

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Simple screening method to identify toxic/non-toxic ionic liquids: agar diffusion test adaptation. Ventura SP, de Barros RL, Sintra T, et al. Ecotoxicol. Environ. Saf. 83, 55-62, (2012)

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Reactive oxygen species and the bacteriostatic and bactericidal effects of isoconazole nitrate. Czaika VA, Siebenbrock J, Czekalla F, et al. Mycoses 56 Suppl 1, 16-22, (2013)

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Biologically active arborinane-type triterpenoids and anthraquinones from Rubia yunnanensis. Jun-Ting Fan et al J. Nat. Prod. 74, 2069-80, (2011)

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Design, synthesis and antimicrobial activity of chiral 2-(substituted-hydroxyl)-3-(benzo[d]oxazol-5-yl)propanoic acid derivatives. Wei Zhang et al Eur. J. Med. Chem. 46, 3639-50, (2011)

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Synthesis of 1,2,3-triazole derivatives and in vitro antifungal evaluation on Candida strains. Lima-Neto RG, Cavalcante NN, Srivastava RM, et al. Molecules 17(5), 5882-92, (2012)

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Antimicrobial selaginellin derivatives from Selaginella pulvinata. Yuan Cao et al Bioorg. Med. Chem. Lett. 20, 2456-60, (2010)

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Blockade of K+ and Ca2+ channels by azole antifungal agents in neonatal rat ventricular myocytes. Sung DJ, Kim JG, Won KJ, et al. Biol. Pharm. Bull. 35(9), 1469-75, (2012)

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Synthesis of some 3-substituted amino-4,5-tetramethylene thieno[2,3-d][ 1,2,3]-triazin-4(3H)-ones as potential antimicrobial agents. Janardhanan Saravanan et al Eur. J. Med. Chem. 45, 4365-9, (2010)

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Prevention of infectious morbidity after elective abdominal hysterectomy. Uysal A, Taner CE, Mun S, et al. Arch. Gynecol. Obstet. 286(4), 959-63, (2012)

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Solid state solubility of miconazole in poly[(ethylene glycol)-g-vinyl alcohol] using hot-melt extrusion. Litvinov VM, Guns S, Adriaensens P, et al. Mol. Pharm. 9(10), 2924-32, (2012)

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Rapid relief of intertrigo-associated pruritus due to Candida albicans with isoconazole nitrate and diflucortolone valerate combination therapy. Veraldi S Mycoses 56 Suppl 1, 41-3, (2013)

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Isoconazole nitrate: a unique broad-spectrum antimicrobial azole effective in the treatment of dermatomycoses, both as monotherapy and in combination with corticosteroids. Veraldi S Mycoses 56 Suppl 1, 3-15, (2013)

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Prophylactic oral/topical non-absorbed antifungal agents to prevent invasive fungal infection in very low birth weight infants. Austin N, Darlow BA, and McGuire W Cochrane Database Syst. Rev. 3, CD003478, (2013)

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DHEA metabolites activate estrogen receptors alpha and beta. Miller KK, Al-Rayyan N, Ivanova MM, et al. Steroids 78(1), 15-25, (2013)

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Effective treatment of erythrasma-associated inflammation and pruritus with isoconazole nitrate and diflucortolone valerate combination therapy. Piergiorgio M Mycoses 56 Suppl 1, 38-40, (2013)

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Trichophyton mentagrophytes cause underestimated contagious zoophilic fungal infection. Czaika VA and Lam PA Mycoses 56 Suppl 1, 33-7, (2013)

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Effective treatment of tinea corporis due to Trichophyton mentagrophytes with combined isoconazole nitrate and diflucortolone valerate therapy. Czaika VA Mycoses 56 Suppl 1, 30-2, (2013)

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Misdiagnosed zoophile tinea faciei and tinea corporis effectively treated with isoconazole nitrate and diflucortolone valerate combination therapy. Czaika VA Mycoses 56 Suppl 1, 26-9, (2013)

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Inflammatory tinea pedis with bacterial superinfection effectively treated with isoconazole nitrate and diflucortolone valerate combination therapy. Friedrich M Mycoses 56 Suppl 1, 23-5, (2013)

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A genetic and pharmacological analysis of isoprenoid pathway by LC-MS/MS in fission yeast. Takami T, Fang Y, Zhou X, et al. PLoS ONE 7(11), e49004, (2012)

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Miconazole nitrate oral disintegrating tablets: in vivo performance and stability study. Ahmed TA, El-Say KM, Mahmoud MF, et al. AAPS PharmSciTech 13(3), 760-71, (2012)

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Peel bond strength of resilient liner modified by the addition of antimicrobial agents to denture base acrylic resin. Alcântara CS, Macêdo AF, Gurgel BC, et al. J. Appl. Oral Sci. 20(6), 607-12, (2012)

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HPLC and chemometric methods for the simultaneous determination of miconazole nitrate and nystatin. Heneedak HM, Salama I, Mostafa S, et al. J. Chromatogr. Sci. 50(10), 855-61, (2012)

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[Fungi isolated from the vagina and their susceptibility to antifungals]. Macura AB and Skóra M Ginekol. Pol. 83(6), 433-8, (2012)

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Analysis of responses to the TRPV4 agonist GSK1016790A in the pulmonary vascular bed of the intact-chest rat. Pankey EA, Zsombok A, Lasker GF, et al. Am. J. Physiol. Heart Circ. Physiol. 306(1), H33-40, (2014)

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Multicenter, double-blind, parallel group study investigating the non-inferiority of efficacy and safety of a 2% miconazole nitrate shampoo in comparison with a 2% ketoconazole shampoo in the treatment of seborrhoeic dermatitis of the scalp. Buechner SA J. Dermatolog. Treat. 25(3), 226-31, (2014)

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In vitro miconazole susceptibility of meticillin-resistant Staphylococcus pseudintermedius and Staphylococcus aureus. Weese JS, Walker M, and Lowe T Vet. Dermatol. 23(5), 400-e74, (2012)

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