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Sigma-Aldrich

Ketoconazol

Synonym(e):

(±)-cis-1-Acetyl-4-{4-{[2-(2,4-dichlorphenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]-methoxy}-phenyl}-piperazin

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About This Item

Empirische Formel (Hill-System):
C26H28Cl2N4O4
CAS-Nummer:
65277-42-1
Molekulargewicht:
531.43
EG-Nummer:
265-667-4
MDL-Nummer:
MFCD00058579
UNSPSC-Code:
12161501
PubChem Substanz-ID:
24724652
NACRES:
NA.77

Assay

≥99% (HPLC)

Form

solid

Farbe

white to light yellow

Löslichkeit

DMSO: soluble

Wirkungsspektrum von Antibiotika

fungi
yeast

Wirkungsweise

enzyme | inhibits

Ersteller

Johnson & Johnson

Lagertemp.

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

InChIKey

XMAYWYJOQHXEEK-OZXSUGGESA-N

Angaben zum Gen

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)

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Anwendung

Ketoconazole has been used as a cytochrome P450 (CYP) inhibitor to study its functions in embryonic testes of rats. Ketoconazole has also been used for the screening of antimicrobial agents against nonreplicating M. tuberculosis. Furthermore, studies have used ketoconazole for antifungal susceptibility testing and also as a standard antifungal agent.
CYP3A4 Inhibitor

Biochem./physiol. Wirkung

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.
Antifungales Mittel

Leistungsmerkmale und Vorteile

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.

Verpackung

Bottomless glass bottle. Contents are inside inserted fused cone.

Angaben zur Herstellung

Ketoconazole is soluble in DMSO.

Signalwort

Danger

Gefahreneinstufungen

Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Repr. 1B - STOT RE 2

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Analysenzertifikate (COA)

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Sigma-Aldrich

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USP

USP

1443409

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Sigma-Aldrich

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