Grundinformationen
- Standard-SMILES
C[C@](N)(Cc1ccc(O)cc1)C(=O)O- InChIKey
NHTGHBARYWONDQ-JTQLQIEISA-N- Summenformel
- C10H13NO3
- Durchschnittliche Molmasse
- 195,21 g/mol
- Monoisotopische Masse
- 195,08954328
Überblick
Alpha-methyl-L-tyrosine is an L-tyrosine derivative that consists of L-tyrosine bearing an additional methyl substituent at position 2. An inhibitor of the enzyme tyrosine 3-monooxygenase, and consequently of the synthesis of catecholamines. It is used to control the symptoms of excessive sympathetic stimulation in patients with pheochromocytoma. It has a role as an antihypertensive agent and an EC 1.14.16.2 (tyrosine 3-monooxygenase) inhibitor. It is a L-tyrosine derivative and a non-proteinogenic L-alpha-amino acid.
Namen und Bezeichner
- Bevorzugter Name
- Metyrosine
- IUPAC
- (2S)-2-amino-3-(4-hydroxyphenyl)-2-methylpropanoic acid
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
672-87-7- PubChem CID
- 441350
- DTXSID
DTXSID6023315- ChEMBL
CHEMBL1200862- ChEBI
CHEBI:6912- UNII
- DOQ0J0TPF7
- EC Number
- 211-599-5
- Nikkaji
- J9.465J
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -1,6
- Polarare Oberfläche (TPSA)
- 83,6 Ų
- H-Brücken-Donoren
- 3
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 3
- Schwere Atome
- 14
- Formalladung
- 0
- Komplexität
- 211
Experimentelle und physikochemische Eigenschaften
Solubility
Very slightly soluble
2.48e+00 g/L
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P270, P271, P301+P317, P304+P340, P319, P330, P403+P233, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Gefahrenhinweise
Toxikologische Informationen
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Metyrosine
vNo-DILI-concern
0
No match
DOI:10.1016/j.drudis.2016.02.015
Chemie und Industrie
Pharmakologische Informationen
ATC Code
C - Cardiovascular system
QC - Cardiovascular system
Pharmacodynamics
In patients with pheochromocytoma, who produce excessive amounts of norepinephrine and epinephrine, administration of one to four grams of metyrosine per day has reduced catecholamine biosynthesis from about 35 to 80 percent as measured by the total excretion of catecholamines and their metabolites (metanephrine and vanillylmandelic acid). The maximum biochemical effect usually occurs within two to three days, and the urinary concentration of catecholamines and their metabolites usually returns to pretreatment levels within three to four days after metyrosine is discontinued. Most patients with pheochromocytoma treated with metyrosine experience decreased frequency and severity of hypertensive attacks with their associated headache, nausea, sweating, and tachycardia. In patients who respond, blood pressure decreases progressively during the first two days of therapy with metyrosine; after withdrawal, blood pressure usually increases gradually to pretreatment values within two to three days.
Mechanism of Action
Metyrosine inhibits tyrosine hydroxylase, which catalyzes the first transformation in catecholamine biosynthesis, i.e., the conversion of tyrosine to dihydroxyphenylalanine (DOPA). Because the first step is also the rate-limiting step, blockade of tyrosine hydroxylase activity results in decreased endogenous levels of catecholamines and their synthesis. This consequently, depletes the levels of the catecholamines dopamine, adrenaline and noradrenaline in the body,usually measured as decreased urinary excretion of catecholamines and their metabolites. One main end result of the catecholamine depletion is a decrease in blood presure.
FDA Pharmacological Classification
DOQ0J0TPF7
METYROSINE
Established Pharmacologic Class [EPC] - Catecholamine Synthesis Inhibitor
Mechanisms of Action [MoA] - Catecholamine Synthesis Inhibitors
Metyrosine is a Catecholamine Synthesis Inhibitor. The mechanism of action of metyrosine is as a Catecholamine Synthesis Inhibitor.
METYROSINE
Absorption, Distribution and Excretion
Well absorbed from the gastrointestinal tract.
Because the first step is also the rate-limiting step, blockade of tyrosine hydroxylase activity results in decreased endogenous levels of catecholamines, usually measured as decreased urinary excretion of catecholamines and their metabolites.
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