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,
• assay: ≥99% (HPLC)
• form: solid
• 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
• 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)

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. 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.

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