metyrapone   Click here for help

GtoPdb Ligand ID: 5224

Synonyms: mepyrapone | Metopirone®
Approved drug PDB Ligand
metyrapone is an approved drug (FDA (1961))
Compound class: Synthetic organic
Comment: Metyrapone is a reversible inhibitor of steroid 11β-hydroxylase (gene symbol CYP11B1).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 0
Rotatable bonds 3
Topological polar surface area 42.85
Molecular weight 226.11
XLogP 1.85
No. Lipinski's rules broken 0
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Canonical SMILES O=C(C(c1cccnc1)(C)C)c1cccnc1
Isomeric SMILES O=C(C(c1cccnc1)(C)C)c1cccnc1
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
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Summary of Clinical Use Click here for help
Used as a diagnostic tool for testing of hypothalamic-pituitary function. Also occasionally used in the treatment of Cushing's syndrome.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Metyrapone is an inhibitor of the 11-β-hydroxylase enzyme, CYP11B1. Inhibition of this enzyme reduces endogenous corticosteroid synthesis in the adrenal gland. This reverses the inhibitory feedback mechanism exerted by cortisol and results in an increase in adrenocorticotropic hormone (ACTH) production by the pituitary.