An 11β-hydroxylase inhibitor
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Metyrapone

Item No. 14994

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-methyl-1,2-di-3-pyridinyl-1-propanone
CAS Number
54-36-4
Synonyms
  • NSC 25265
  • SU 4885
Molecular Formula
C14H14N2O
Formula Weight
226.3
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/mlPBS (pH 7.2): 5 mg/ml
λmax
231, 264 nm
SMILES
O=C(C1=CN=CC=C1)C(C)(C)C2=CC=CN=C2
InChi Code
InChI=1S/C14H14N2O/c1-14(2,12-6-4-8-16-10-12)13(17)11-5-3-7-15-9-11/h3-10H,1-2H3
InChi Key
FJLBFSROUSIWMA-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    250 mg

    $28

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    500 mg

    $48

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    1 g

    $84

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    Product Description

    Metyrapone is an inhibitor of the cytochrome P450 (CYP) enzyme 11β-hydroxylase (IC50 = 7.83 µM), an enzyme involved in the final step of cortisol biosynthesis.1 It also induces Cyp1a1 and Cyp3a4 expression in rat hepatic microsomes and inhibits the activity of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) in sheep liver microsomes.2,3,4 Metyrapone (150 mg/kg, s.c.) suppresses hypoxia-ischemia-induced increases in plasma corticosterone levels and seizures in rats.5 It also reduces ethanol consumption in alcohol high-preferring rats.6 Formulations containing metyrapone have been used in the diagnosis of adrenal insufficiency and the treatment of Cushing’s disease.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hays, S.J., Tobes, M.C., Gildersleeve, D.L., et al. Structure-activity relationship study of the inhibition of adrenal cortical 11β-hydroxylase by new metyrapone analogues. J. Med. Chem. 27(1), 15-19 (1984).

    2. Harvey, J.L., Paine, A.J., and Wright, M.C. Disruption of endogenous regulator homeostasis underlies the mechanism of rat CYP1A1 mRNA induction by metyrapone. Biochem. J. 331(1), 273-281 (1998).

    3. Paine, A.J., Villa, P., and Hockin, L.J. Evidence that ligand formation is a mechanism underlying the maintenance of cytochrome P-450 in rat liver cell culture. Potent maintenance by metyrapone. Biochem. J. 188(3), 937-939 (1980).

    4. Sampath-Kumar, R., Yu, M., Khalil, M.W., et al. Metyrapone is a competitive inhibitor of 11β-hydroxysteroid dehydrogenase type 1 reductase. J. Steroid Biochem. Mol. Biol. 62(2-3), 195-199 (1997).

    5. Krugers, H.J., Kemper, R.H., Korf, J., et al. Metyrapone reduces rat brain damage and seizures after hypoxia-ischemia: An effect independent of modulation of plasma corticosterone levels? J. Cereb. Blood Flow Metab. 18(4), 386-390 (1998).

    6. Fahlke, C., Hård, E., Thomasson, R., et al. Metyrapone-induced suppression of corticosterone synthesis reduces ethanol consumption in high-preferring rats. Pharmacol. Biochem. Behav. 48(4), 977-981 (1994).