alpha-methyltyrosine   Click here for help

GtoPdb Ligand ID: 6956

Synonyms: Demser® | metyrosine | MK-781
Approved drug
alpha-methyltyrosine is an approved drug (FDA (1979))
Compound class: Synthetic organic
Comment: The US FDA approved name for this compound is metyrosine, an inhibitor of tyrosine 3-hydroxylase enzymatic activity.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 3
Rotatable bonds 3
Topological polar surface area 83.55
Molecular weight 195.09
XLogP -1.68
No. Lipinski's rules broken 0
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Canonical SMILES Oc1ccc(cc1)CC(C(=O)O)(N)C
Isomeric SMILES Oc1ccc(cc1)C[C@@](C(=O)O)(N)C
InChI InChI=1S/C10H13NO3/c1-10(11,9(13)14)6-7-2-4-8(12)5-3-7/h2-5,12H,6,11H2,1H3,(H,13,14)/t10-/m0/s1
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Summary of Clinical Use Click here for help
Metyrosine is used to treat tumours of the adrenal gland known as pheochromocytoma. These tumours over-produce catecholamines and thereby cause hyperstimulation of the sympathetic nervous system.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
It is hypothesised that metyrosine disrupts the synthesis of catecholamines by acting as an inhibitor of tyrosine hydroxylase, with in vivo human results to support this hypothesis [1].