Skip to Content
Merck
All Photos(1)

Key Documents

420600

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Alexey Fayzullin et al.
Stem cell research & therapy, 13(1), 317-317 (2022-07-17)
One of the severe complications occurring because of the patient's intubation is tracheal stenosis. Its incidence has significantly risen because of the COVID-19 pandemic and tends only to increase. Here, we propose an alternative to the donor trachea and synthetic

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service