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Submit ReviewKetoconazole is an 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.
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.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solvent | Max Conc. mg/mL | Max Conc. mM | |
---|---|---|---|
Solubility | |||
ethanol | 26.57 | 50 | |
DMSO | 39.86 | 75 |
The following data is based on the product molecular weight 531.44. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
---|---|---|---|
0.75 mM | 2.51 mL | 12.54 mL | 25.09 mL |
3.75 mM | 0.5 mL | 2.51 mL | 5.02 mL |
7.5 mM | 0.25 mL | 1.25 mL | 2.51 mL |
37.5 mM | 0.05 mL | 0.25 mL | 0.5 mL |
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 560 372 PMID: 30046109
Madhavan et al (2018) Induction of myelinating oligodendrocytes in human cortical spheroids. Nat.Methods. 15 700 PMID: 30046099
If you know of a relevant reference for Ketoconazole, please let us know.
Keywords: Ketoconazole, Ketoconazole supplier, Cytochrome, P450c17, inhibitors, inhibits, CYP, antifingal, promotes, myelination, oligodendrocyte, differentiation, P450, Other, Differentiation, Products, 1103, Tocris Bioscience
Citations are publications that use Tocris products. Selected citations for Ketoconazole include:
Lu et al (2019) Inhibition of proliferation and migration of melanoma cells by ketoconazole and Ganoderma immunomodulatory proteins. Oncol Lett 18 891 PMID: 31289567
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
Ruparel et al (2012) The cytochrome P450 inhibitor, ketoconazole, inhibits oxidized linoleic acid metabolite-mediated peripheral inflammatory pain. Mol Pain 8 73 PMID: 23006841
Green et al (2013) Role of endogenous TRPV1 agonists in a postburn pain model of partial-thickness injury. Pain 154 2512 PMID: 23891895
Do you know of a great paper that uses Ketoconazole from Tocris? Please let us know.
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