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Ketoconazole

SIGMA/K1003 - 99.0-101.0% (EP, titration)

Synonym: (±)-cis-1-Acetyl-4-(4-[(2-[2,4-dichlorophenyl]-2-[1H-imidazol-1-ylmethyl]-1,3-dioxolan-4-yl)-methoxy]phenyl)piperazine

CAS Number: 65277-42-1
Empirical Formula (Hill Notation): C26H28Cl2N4O4
Molecular Weight: 531.43
EC Number: 265-667-4
MDL Number: MFCD00058579
Linear Formula: C26H28Cl2N4O4
Product Type: Chemical

Catalog Number PKG Qty. Price Quantity
45-K1003-100MG 100 mg
$185.00
1/EA
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This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: K1003-100MG

 

antibiotic activity spectrum fungi
  Gram-positive bacteria
  yeast
assay 99.0-101.0% (EP, titration)
color white to off-white
description Specific Optical Rotation (EP): (−0.10) ∼ +0.10 °
form powder
InChI 1S/C26H28Cl2N4O4/c1-19(33)31-10-12-32(13-11-31)21-3-5-22(6-4-21)34-15-23-16-35-26(36-23,17-30-9-8-29-18-30)24-7-2-20(27)14-25(24)28/h2-9,14,18,23H,10-13,15-17H2,1H3/t23-,26-/m0/s1
InChI key XMAYWYJOQHXEEK-OZXSUGGESA-N
mode of action enzyme | inhibits
Quality Level 200 
SMILES string CC(=O)N1CCN(CC1)c2ccc(OC[C@H]3CO[C@@](Cn4ccnc4)(O3)c5ccc(Cl)cc5Cl)cc2
storage temp. 2-8°C
Application: CYP3A4 inhibitor
Application: Ketoconazole is a broad spectrum antifungal agent used to treat candidiasis, chronic mucocutaneous candidiasis, oral thrush, candiduria, blastomycosis, coccidioidomycosis, histoplasmosis, chromomycosis, and paracoccidioidomycosis. It is used to identify p-glycoprotein/CYP3A-limited bioavailability in the monkey model, to study interleukin 1 mediated antitumor effects, and drug interactions in vivo
Biochem/physiol Actions: Antifungal agent
Biochem/physiol Actions: Ketoconazole interacts with 14-α demethylase, a cytochrome P-450 enzyme that is necessary for the conversion of lanosterol to ergosterol. This interaction inhibits ergosterol synthesis and results in increased fungal cellular permeability. Other possible mechanisms of action are the inhibition of endogenous respiration, interaction with membrane phospholipids, inhibition of yeast transformation to mycelial forms, inhibition of purine uptake, and impairment of triglyceride and/or phospholipid biosynthesis. Ketoconazole inhibits the synthesis of thromboxane and sterols such as aldosterone, cortisol, and testosterone .
General description: Chemical structure: imidazole
Packaging: 100 mg in glass bottle
Purity 99.0-101.0% (EP, titration)
Storage Temp. 2-8°C
UNSPSC 51101500

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