UC280

Ketoconazol

≥99% (HPLC), Cytochrome P450c17 inhibitor, solid

• Synonym(e): (±)-cis-1-Acetyl-4-{4-{[2-(2,4-dichlorphenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]-methoxy}-phenyl}-piperazin
• Empirische Formel (Hill-System): C₂₆H₂₈Cl₂N₄O₄
• CAS-Nummer: 65277-42-1
• Molekulargewicht: 531.43
• NACRES: NA.77
• PubChem Substance ID: 24724652
• UNSPSC Code: 12161501
• EC Number: 265-667-4
• MDL number: MFCD00058579
• Assay: ≥99% (HPLC)
• Form: solid

Eigenschaften

• Produktname: Ketoconazol,
• form: solid
• 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
• SMILES string: CC(=O)N1CCN(CC1)c2ccc(OC[C@H]3CO[C@@](Cn4ccnc4)(O3)c5ccc(Cl)cc5Cl)cc2
• assay: ≥99% (HPLC)
• color: white to light yellow
• solubility: DMSO: soluble
• antibiotic activity spectrum: fungi, yeast
• mode of action: enzyme | inhibits
• originator: Johnson & Johnson
• storage temp.: 2-8°C
• 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)

Beschreibung

Application

CYP3A4 Inhibitor

Ketoconazole has been used as a cytochrome P450 (CYP) inhibitor to study its functions in embryonic testes of rats[1]. Ketoconazole has also been used for the screening of antimicrobial agents against nonreplicating M. tuberculosis[2]. Furthermore, studies have used ketoconazole for antifungal susceptibility testing[3] and also as a standard antifungal agent[4].

Biochem/physiol Actions

Antifungales Mittel

Ketoconazole is an imidazole derivative.[5] It plays an important role in inhibiting the conversion of lanosterol to ergosterol in the cell wall of fungi. Ketoconazole has therapeutic effects against dermatophytosis, superficial candidiasis, and paracoccidioidomycosis.[6]

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

This compound was developed by Johnson & Johnson. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Preparation Note

Ketoconazole is soluble in DMSO[1].

Sicherheitshinweise

• 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
• Lagerklasse: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges