1-[2-(2,4-dichlorophenyl)-2-[(2,4-dichlorophenyl)methoxy]ethyl]-1H-imidazole; nitric acid

• ChemBase ID: 72827
• Molecular Formular: C18H15Cl4N3O4
• Molecular Mass: 479.1414
• Monoisotopic Mass: 476.9816667
• SMILES: c1c(cc(c(c1)C(OCc1ccc(cc1Cl)Cl)Cn1ccnc1)Cl)Cl.O[N+](=O)[O-]
• Canonical SMILES: Clc1ccc(c(c1)Cl)COC(c1ccc(cc1Cl)Cl)Cn1cncc1.[O-][N+](=O)O
• InChI: InChI=1S/C18H14Cl4N2O.HNO3/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;2-1(3)4/h1-8,11,18H,9-10H2;(H,2,3,4)
• InChIKey: MCCACAIVAXEFAL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[2-(2,4-dichlorophenyl)-2-[(2,4-dichlorophenyl)methoxy]ethyl]-1H-imidazole; nitric acid
• IUPAC Traditional name: miconazole; nitric acid; acid, nitric; miconazole
• Synonyms: Fungisdin; Albistat; Andergin; Daktacort; Miconazole nitrate; 1-[2,4-Dichloro β-([2,4-dichloro-benzyl]oxy]phenethyl]imidazole; (±)-MICONAZOLE NITRATE; 1-(2,4-Dichloro-β-[(2,4-dichlorobenzyl)oxy]phenethyl)imidazole; (±)-Miconazole nitrate salt

Database IDs

• CAS Number: 22832-87-7; 75319-48-1
• EC Number: 245-256-6
• MDL Number: MFCD00058161
• PubChem SID: 162037748; 24896848
• PubChem CID: 68553

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 5.4261637
• LogD (pH = 7.4): 5.89066
• Log P: 5.9563684
• Molar Refractivity: 103.0676 cm^3
• Polarizability: 40.009266 Å^3
• Polar Surface Area: 27.05 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 180°C

Safety Information

• Storage Condition: -20°C; Room Temperature (15-30°C)
• RTECS: NI4771000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-43
• Safety Statements: 36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H317
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: room temp

Product Information

• Grade: certified reference material
• Salt Data: Nitrate
• Packaging: pkg of 1 g
• Suitability: suitable for 1694 per US EPA
• Pharmacopeia Traceability: traceable to BP 253; traceable to PhEur M1900000; traceable to USP 1443500
• Empirical Formula (Hill Notation): C18H14Cl4N2O · HNO3

DETAILS

MP Biomedicals - 02151693

Crystalline

Selleck Chemicals - S1956

Research Area: Infection
Biological Activity:
Miconazole is an imidazole antifungal agent that is used topically and by intravenous infusion. Miconazole interacts with 14-α demethylase, a cytochrome P-450 enzyme necessary to convert lanosterol to ergosterol. As ergosterol is an essential component of the fungal cell membrane, inhibition of its synthesis results in increased cellular permeability causing leakage of cellular contents. Miconazole may also inhibit egndogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms, inhibit purine uptake, and impair triglyceride and/or phospholipid biosynthesis. [1]

Sigma Aldrich - M3512

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.

Sigma Aldrich - PHR1163

General description
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO Guide 34.
Other Notes
Values of analytes vary lot to lot.
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.

REFERENCES

• http://www.drugbank.ca/drugs/DB01110