Ketoconazole

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Cat.No. 1103 - Ketoconazole | C26H28Cl2N4O4 | CAS No. 65277-42-1
Description: Cytochrome P450c17 inhibitor
Chemical Name: cis-1-Acetyl-4-[4-[[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl] methoxy]phenyl]piperazine
Purity: ≥99% (HPLC)
Datasheet
Citations (3)
Reviews
Literature

Biological Activity

Inhibitor of cytochrome P450c17. Enhances the formation of myelin basic protein-positive oligodendrocytes from oligodendrocyte progenitor cells in vitro and promotes remyelination in vivo. Also an antifungal agent. Brain penetrant.

Technical Data

M. Wt 531.44
Formula C26H28Cl2N4O4
Storage Desiccate at +4°C
Purity ≥99% (HPLC)
CAS Number 65277-42-1
PubChem ID 456201
InChI Key XMAYWYJOQHXEEK-OZXSUGGESA-N
Smiles ClC1=CC(Cl)=[C@]([C@]3(OC[C@@](COC4=CC=C(N5CCN(C(C)=O)CC5)C=C4)([H])O3)CN2C=CN=C2)C=C1

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
ethanol 26.57 50
DMSO 39.86 75

Preparing Stock Solutions

The following data is based on the product molecular weight 531.44. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.88 mL 9.41 mL 18.82 mL
5 mM 0.38 mL 1.88 mL 3.76 mL
10 mM 0.19 mL 0.94 mL 1.88 mL
50 mM 0.04 mL 0.19 mL 0.38 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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Safety Datasheet

References

References are publications that support the biological activity of the product.

Ayub and Levell (1989) Inhibition of human adrenal steroidogenic enzymes in vitro by imidazole drugs including ketoconazole. J.Steroid Biochem. 32 515 PMID: 2724954

Dumaine et al (1998) Blockade of HERG and Kv1.5 by ketoconazole. J.Pharmacol.Exp.Ther. 286 727 PMID: 9694927

Kuhn-Velten et al (1992) Ketoconazole inhibition of the bifunctional cytochrome P450c17 does not affect androgen formation from the endogenous lyase substrate. Biochem.Pharmacol. 44 2371 PMID: 1472102

Merck Index 12 5313

Hubler et al (2018) Accumulation of 8,9-unsaturated sterols drives oligodendrocyte formation and remyelination. Nature PMID: 30046109

Madhavan et al (2018) Induction of myelinating oligodendrocytes in human cortical spheroids. Nat.Methods. PMID: 30046099


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Keywords: Ketoconazole, Ketoconazole supplier, Cytochrome, P450c17, inhibitors, inhibits, CYP, antifingal, promotes, myelination, oligodendrocyte, differentiation, P450, Other, Differentiation, Products, 1103, Tocris Bioscience

3 Citations for Ketoconazole

Citations are publications that use Tocris products. Selected citations for Ketoconazole include:

Green et al (2016) Central activation of TRPV1 and TRPA1 by novel endogenous agonists contributes to mechanical allodynia and thermal hyperalgesia after burn injury. Mol Pain 12 PMID: 27411353

Green et al (2013) Role of endogenous TRPV1 agonists in a postburn pain model of partial-thickness injury. Pain 154 2512 PMID: 23891895

Ruparel et al (2012) The cytochrome P450 inhibitor, ketoconazole, inhibits oxidized linoleic acid metabolite-mediated peripheral inflammatory pain. Mol Pain 8 73 PMID: 23006841


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Literature in this Area

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