1443500

Miconazolnitrat

United States Pharmacopeia (USP) Reference Standard

• Synonym(e): (±)-Miconazol -nitrat (Salz), 1-(2,4-Dichlor-β-[(2,4-dichlorbenzyl)-oxy]-phenethyl)-imidazol
• Empirische Formel (Hill-System): C₁₈H₁₄Cl₄N₂O · HNO₃
• CAS-Nummer: 22832-87-7
• Molekulargewicht: 479.14
• NACRES: NA.24
• PubChem Substance ID: 329750464
• UNSPSC Code: 41116107
• MDL number: MFCD00058161

Eigenschaften

• grade: pharmaceutical primary standard
• agency: USP
• API family: miconazole
• manufacturer/tradename: USP
• application(s): pharmaceutical (small molecule)
• format: neat
• SMILES string: ClC1=CC(Cl)=CC=C1C(OCC2=CC=C(Cl)C=C2Cl)CN3C=CN=C3.[O-][N+](O)=O
• 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)
• InChI key: MCCACAIVAXEFAL-UHFFFAOYSA-N

Beschreibung

General description

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia.For further information and support please go to the website of the issuing Pharmacopoeia.

Application

Miconazole nitrate USP reference standard, intended for use in specified quality tests and assays as specified in the USP compendia. Also, for use with USP monographs such as:

• Miconazole Nitrate Cream
• Miconazole Nitrate Topical Powder
• Miconazole Nitrate Vaginal Suppositories

Biochem/physiol Actions

Antifungales Azol. Wirkungsweise: inhibiert Cytochrom P450-abhängige 14α-Demethylase, die für die Ergosterin-Biosynthese wichtig ist. Die kumulierten 14α-methylierten Sterole ändern die Membranstruktur sensitiver Pilze, was eine geänderte Permeabilität der Zellmembran zur Folge hat. Es inhibiert auch Peroxidasen, wodurch Peroxide in der Zelle angereichert werden.

Miconazol interagiert mit 14-α-Demethylase, einem Cytochrom-P-450-Enzym, das für die Ergosterin-Biosynthese notwendig ist. Die Hemmung von Ergosterol führt zu einer erhöhten zellulären Permeabilität, was zum Leckverlust zellulärer Inhalte führt. Miconazol kann auch endogene Atmung inhibieren, mit Phospholipiden der Zellmembran interagieren, die Transformation von Hefen zu Myzel Formen hemmen, die Purin-Aufnahme hemmen und in die Triglycerid und Phospholipidbiosynthese eingreifen.

Analysis Note

These products are for test and assay use only. They are not meant for administration to humans or animals and cannot be used to diagnose, treat, or cure diseases of any kind.  ​

Other Notes

Sales restrictions may apply.

Sicherheitshinweise

• pictograms: GHS07
• signalword: Warning
• hcodes: H302,H317
• Hazard Classifications: Acute Tox. 4 Oral - Skin Sens. 1
• Lagerklasse: 11 - Combustible Solids
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• pcodes: P261 - P264 - P272 - P280 - P301 + P312 - P302 + P352