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Sigma-Aldrich

Ketoconazole

An inhibitor of cytochrome P-450 in steroid biosynthesis. An antifungal agent that displays potent anti-metastatic, anti-neoplastic, and anti-psoriatic activities.

Synonym(s):

Ketoconazole, cis-1-Acetyl-4-[4-[[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazine, R-41400, CYP17A1 Inhibitor I

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About This Item

Empirical Formula (Hill Notation):
C26H28Cl2N4O4
CAS Number:
65277-42-1
Molecular Weight:
531.43
MDL number:
MFCD00058579
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

solid

potency

26 μM IC50

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze

color

off-white

shipped in

ambient

storage temp.

2-8°C

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-/m1/s1

InChI key

XMAYWYJOQHXEEK-ZEQKJWHPSA-N

General description

An inhibitor of cytochrome P-450 in steroid biosynthesis. An anti-fungal agent that displays potent anti-metastatic, anti-neoplastic, and anti-psoriatic activities. Also acts as an inhibitor of 5-lipoxygenase (5-LO; IC50 = 26 µM) and thromboxane synthase activities.
An inhibitor of cytochrome P-450 in steroid biosynthesis. An antifungal agent that displays potent anti-metastatic, anti-neoplastic, and anti-psoriatic activities. Also acts as an inhibitor of 5-lipoxygenase (5-LO; IC50 = 26 µM) and thromboxane synthase activities.

Biochem/physiol Actions

Primary Target
5-LO

Warning

Toxicity: Toxic & Carcinogenic / Teratogenic (G)

Other Notes

Due to the nature of the Hazardous Materials in this shipment, additional shipping charges may be applied to your order. Certain sizes may be exempt from the additional hazardous materials shipping charges. Please contact your local sales office for more information regarding these charges.
van Wauwe, J.P., and Janssen, P.A.J. 1989. J. Med. Chem. 32, 2231.
Beetens, J.R., et al. 1986. Biochem. Pharmacol. 35, 883.
Lambert, A., et al. 1986. Biochem. Pharmacol. 35, 3999.
Tucker, W.F.G., and MacNeil, S. 1986. Br. Med. J. 293, 882.
Lelcuk, S., et al. 1984. J. Trauma 24, 393.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Signal Word

Danger

Hazard Statements

H301,H360F,H373,H410

Hazard Classifications

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

Storage Class Code

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

Certificates of Analysis (COA)

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