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Metyrapone

Catalog No.
B7347
An 11β-hydroxylase (CYP11B1) inhibitor
Grouped product items
SizePriceStock Qty
10mM (in 1mL H2O)
$55.00
In stock
50mg
$50.00
In stock
For scientific research use only and should not be used for diagnostic or medical purposes.

Tel: +1-832-696-8203

Email: [email protected]

Worldwide Distributors

Background

Metyrapone is a cytochrome P450 (CYP) inhibitor. Metyrapone inhibits 11β-hydroxylase (CYP11B1), a key enzyme involved in the final step of cortisol biosynthesis, with an IC50 value of 7.83 μM. Also, metyrapone inhibits other steroidogenic enzymes (e.g. cholesterol side chain cleavage enzyme) at high concentrations. Administration of metyrapone to man and animals (e.g. dogs and sheep) results in a decrease in circulating levels of cortisol. Thus, metyrapone has been used clinically for diagnostic and therapeutic purposes.?

References:

1.?Sampath-Kumar R, Yu M, Khalil MW, et al. Metyrapone is a competitive inhibitor of 11β-hydroxysteroid dehydrogenase type 1 reductase. The Journal of Steroid Biochemistry and Molecular Biology, 1997, 62(2-3): 195-199.

2.?Hays SJ, Tobes MC, Gildersleeve DL, et al. Structure-activity relationship study of the inhibition of adrenal cortical 11β-hydroxylase by new metyrapone analogues. Journal of Medicinal Chemistry, 1984, 27(1): 15-19.

3.?Asakura T, Shichi H. Cytochrome P450-mediated prostaglandin ω/ω-1 hydroxylase activities in porcine ciliary body epithelial cells. Experimental Eye Research, 1992, 55(2): 377-384.

4.?JENKINS JS, MEAKIN JW, NELSON DH, et al. Inhibition of adrenal steroid 11-oxygenation in the dog. Science, 1958, 128(3322): 478-480.

Chemical Properties

Physical AppearanceA solid
StorageStore at -20°C
M.Wt226.27
Cas No.54-36-4
FormulaC14H14N2O
Solubility≥13.45 mg/mL in H2O; ≥42.1 mg/mL in DMSO; ≥59.1 mg/mL in EtOH
Chemical Name2-methyl-1,2-di(pyridin-3-yl)propan-1-one
SDFDownload SDF
Canonical SMILESO=C(C1=CC=CN=C1)C(C)(C)C2=CC=CN=C2
Shipping ConditionSmall Molecules with Blue Ice, Modified Nucleotides with Dry Ice.
General tips We do not recommend long-term storage for the solution, please use it up soon.

Protocol

Cell experiment:[3]

Cell lines

Non-pigmented epithelial (NPE) cells and pigmented epithelial (PE) cells

Reaction Conditions

2 mM metyrapone

Applications

Metyrapone inhibited cytochrome P450-mediated prostaglandin ω/ω-1 hydroxylase activities in NPE and PE cells.
Animal experiment:[4]

Animal models

A 19.3 kg dog

Dosage form

75 mg/kg

Intravenous injection

Applications

A single intravenous injection of metyrapone caused a decrease in adrenal venous 17-hydroxycorticosteroids to 10 percent of the initial value within 10 minutes followed by a return to 75 percent within 3 hours.

Note

The technical data provided above is for reference only.

References:

1. Sampath-Kumar R, Yu M, Khalil MW, et al. Metyrapone is a competitive inhibitor of 11β-hydroxysteroid dehydrogenase type 1 reductase. The Journal of Steroid Biochemistry and Molecular Biology, 1997, 62(2-3): 195-199.

2. Hays SJ, Tobes MC, Gildersleeve DL, et al. Structure-activity relationship study of the inhibition of adrenal cortical 11β-hydroxylase by new metyrapone analogues. Journal of Medicinal Chemistry, 1984, 27(1): 15-19.

3. Asakura T, Shichi H. Cytochrome P450-mediated prostaglandin ω/ω-1 hydroxylase activities in porcine ciliary body epithelial cells. Experimental Eye Research, 1992, 55(2): 377-384.

4. JENKINS JS, MEAKIN JW, NELSON DH, et al. Inhibition of adrenal steroid 11-oxygenation in the dog. Science, 1958, 128(3322): 478-480.

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