K1003

Ketoconazole

99.0-101.0% (EP, titration)

• Sinónimos: (±)-cis-1-Acetyl-4-(4-[(2-[2,4-dichlorophenyl]-2-[1H-imidazol-1-ylmethyl]-1,3-dioxolan-4-yl)-methoxy]phenyl)piperazine
• Fórmula empírica (notación de Hill): C₂₆H₂₈Cl₂N₄O₄
• Número de CAS: 65277-42-1
• Peso molecular: 531.43
• EC Number: 265-667-4
• MDL number: MFCD00058579
• UNSPSC Code: 51101500
• PubChem Substance ID: 24278176
• NACRES: NA.85

Propiedades

• description: Specific Optical Rotation (EP): (−0.10) ∼ +0.10 °
• assay: 99.0-101.0% (EP, titration)
• form: powder
• color: white to off-white
• antibiotic activity spectrum: Gram-positive bacteria; fungi; yeast
• mode of action: enzyme | inhibits
• storage temp.: 2-8°C
• SMILES string: CC(=O)N1CCN(CC1)c2ccc(OC[C@H]3CO[C@@](Cn4ccnc4)(O3)c5ccc(Cl)cc5Cl)cc2
• 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
• Gene Information: human ... ABCB1(5243) , CYP11B1(1584) , CYP11B2(1585) , CYP17A1(1586) , CYP19A1(1588) , CYP1A2(1544) , CYP24A1(1591) , CYP26A1(1592) , CYP3A4(1576) , CYP51A1(1595) , KCNH1(3756) ; mouse ... Abcb1a(18671) , Abcb1b(18669) ; rat ... Alox5(25290) , Cyp17a1(25146) , Cyp51(25427) , Cyp7a1(25428)

Descripción

General description

Chemical structure: imidazole

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

CYP3A4 inhibitor

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 .

Antifungal agent

Información de seguridad

• pictograms: GHS06,GHS08,GHS09
• signalword: Danger
• hcodes: H301,H360F,H373,H410
• pcodes: P202 - P260 - P264 - P273 - P280 - P301 + P310
• Hazard Classifications: Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Repr. 1B - STOT RE 2
• Storage Class: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges