Metyrosine

HCID 441350CAS 672-87-7

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

METYROSINE672-87-7MetirosineDemserMetirosina(2S)-2-amino-3-(4-hydroxyphenyl)-2-methylpropanoic acid(S)-alpha-MethyltyrosineL-alpha-MethyltyrosineMetirosinum(-)-alpha-Methyl-L-tyrosineAlpha-Methyl-L-P-TyrosineMK-781
Weitere Namen anzeigen
DTXSID6023315DOQ0J0TPF7CHEBI:6912L-588357-0DTXCID203315methyl-tyrosineRefChem:56543alpha-Methyltyrosine, (L)-

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

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15
LogP-1.7
Solubility · 2 Einträge

Very slightly soluble

2.48e+00 g/L

Human Drugs · 2 Einträge

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Melting Point312.5 °C
Physical DescriptionSolid

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

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

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Toxikologische Informationen

Drug Induced Liver Injury · 6 Einträge

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 · 2 Einträge

C - Cardiovascular system

QC - Cardiovascular system

Pharmacodynamics · 1 Eintrag

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 · 1 Eintrag

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.

Biological Half-Life3.4 to 3.7 hours
Metabolism/MetabolitesLittle biotransformation, with catechol metabolites accounting for less than 1% of the administered dose.
FDA Pharmacological Classification · 6 Einträge

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

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