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AB144618

Metyrapone, cytochrome P450 inhibitor. Blocks cortisol synthesis.

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MW 226.27 Da, Purity >98%. Selective cytochrome P450 inhibitor (IC50 = 1 μM). Blocks cortisol synthesis in vitro and in vivo. Neuroprotective. Cell and blood-brain barrier permeable.

View Alternative Names

1,8-cineole 2-exo-monooxygenase, ALDOS, Albendazole monooxygenase, Albendazole sulfoxidase, Aldosterone synthase, Aldosterone-synthesizing enzyme, C11B2_HUMAN, CP33, CP34, CP3A4_HUMAN, CYP11B2, CYP3, CYP3A, CYP3A3, CYP3A4, CYPIIIA3, CYPIIIA4, CYPXIB2, Cytochrome P-450Aldo, Cytochrome P-450C18, Cytochrome P450 11B2, Cytochrome P450 11B2, mitochondrial, Cytochrome P450 3A3, Cytochrome P450 3A4, Cytochrome P450 HLp, Cytochrome P450 NF-25, Cytochrome P450 family 3 subfamily A polypeptide 4, Cytochrome P450 subfamily IIIA polypeptide 4, Cytochrome P450-PCN1, Glucocorticoid inducible P450, HLP, MGC126680, NF 25, Nifedipine oxidase, P-450Aldo, P-450C18, P450 III steroid inducible, P450 PCN1, P450, family III, P450C3, Quinine 3-monooxygenase, Steroid 18-hydroxylase, Taurochenodeoxycholate 6-alpha-hydroxylase, cytochrome P450, subfamily IIIA (niphedipine oxidase), polypeptide 3, cytochrome P450, subfamily IIIA (niphedipine oxidase), polypeptide 4, mitochondrial

1 Images
Chemical Structure - Metyrapone, cytochrome P450 inhibitor. Blocks cortisol synthesis. (AB144618)
  • Chemical Structure

Lab

Chemical Structure - Metyrapone, cytochrome P450 inhibitor. Blocks cortisol synthesis. (AB144618)

2D chemical structure image of ab144618, Metyrapone, cytochrome P450 inhibitor. Blocks cortisol synthesis.

Key facts

CAS number

54-36-4

Purity

>98%

Form

Solid

form

Molecular weight

226.27 Da

Molecular formula

C<sub>1</sub><sub>4</sub>H<sub>1</sub><sub>4</sub>N<sub>2</sub>O

PubChem

4174

Nature

Synthetic

Solubility

Soluble in DMSO to 75 mM

Biochemical name

Metyrapone

Biological description

Selective cytochrome P450 inhibitor (IC50 = 1 μM). Blocks cortisol synthesis in vitro and in vivo. Neuroprotective. Cell and blood-brain barrier permeable.

Canonical smiles

CC(C)(C1=CN=CC=C1)C(=O)C2=CN=CC=C2

InChi

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

InChiKey

FJLBFSROUSIWMA-UHFFFAOYSA-N

IUPAC Name

2-methyl-1,2-dipyridin-3-ylpropan-1-one

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Properties and storage information

Shipped at conditions
Ambient - Can Ship with Ice
Appropriate short-term storage conditions
Ambient
Appropriate long-term storage conditions
Ambient
Storage information
The product can be stored for up to 12 months
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Supplementary information

This supplementary information is collated from multiple sources and compiled automatically.

Cytochrome P450 3A4 often abbreviated as CYP3A4 is an enzyme of the cytochrome P450 superfamily. This enzyme has a mass approximately 57 kDa and functions as an important player in the oxidation of small organic molecules during drug metabolism. CYP3A4 is expressed in the liver which is its primary site of expression as well as in the intestine. An alternate enzyme name C11B2 or CYP11B2 sometimes refers to a distinct enzyme involved in steroid biosynthesis. However CYP3A4 is important for metabolizing compounds by facilitating the oxidation of substrates such as lipids and natural compounds.
Biological function summary

CYP3A4 metabolizes a wide range of drugs that are administered therapeutically. It is not part of a multimeric complex but acts on its own to catalyze metabolic reactions. This enzyme facilitates the conversion of lipophilic drugs into more hydrophilic metabolites which become easier for the body to excrete. Moreover CYP3A4 plays a role in steroid hormone biosynthesis contributing to processes like cortisol synthesis where it influences the cortisol molecular structure. The enzyme also participates in the metabolism of endogenous steroids like testosterone and progesterone.

Pathways

CYP3A4 functions centrally in the drug metabolism pathway which is fundamental for the detoxification and elimination of xenobiotics. Another significant pathway involving CYP3A4 is the synthesis and metabolism of cholesterol and steroid hormones. It interacts with proteins such as CYP2C9 which also metabolizes drugs and steroids to ensure chemical homeostasis within the body. These pathways rely heavily on the activity of cytochrome P450 enzymes highlighting their importance in various physiological processes.

CYP3A4 activities can influence the development and management of conditions like liver disease and drug-induced toxicity. Overexpression or inhibition of this enzyme can lead to significant alterations in drug efficacy and safety affecting conditions like chronic liver diseases. In metabolic disorders the enzyme's normal functioning can be hampered influencing cortisol production and leading to imbalanced cortisol chemical structure. Additionally CYP3A4's activity relates to other enzymes such as CYP2D6 which also plays roles in the metabolism of pharmaceuticals and is implicated in metabolic syndrome.
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Product protocols

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