Metirosin
Metyrosine
Daten werden ergänzt – lade die Seite später neu, um den aktuellen Stand zu sehen
Grundinformationen
- CAS
672-87-7- 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
- Lokaler Name
- Metirosin
- Englischer Name
- alpha-Methyl-L-p-tyrosine
- Summenformel
- C10H13NO3
- Molmasse
- 195.22
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
α-Methyl-L-tyrosineα-Me-Tyr-OHAMPTL-AMPTL-α-MTa-Me-Tyr-OHL-Metyrosine
DTXSID6023315DOQ0J0TPF7CHEBI:6912L-588357-0DTXCID203315methyl-tyrosineRefChem:56543alpha-Methyltyrosine, (L)-
Datenbank-Bezeichner
- CAS
672-87-7- PubChem CID
- 441350
- DTXSID
DTXSID6023315- ChEMBL
CHEMBL1200862- ChEBI
CHEBI:6912
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- 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
DrugsPharmaceuticals -> Listed in ZINC15
LogP-1.7
Solubility
Very slightly soluble
2.48e+00 g/L
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Melting Point312.5 °C
Physical DescriptionSolid
Physikochemische Eigenschaften
- Schmelzpunkt
- 320 · 320-340°C dec.
- Siedepunkt
- 383.7 · 383.7±32.0 °C(Predicted)
- Dichte
- 1.283 · 1.283±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- Löslichkeit
- Aqueous Acid (Slightly)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
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
Hazard Classes and CategoriesAcute Tox. 4 (100%)
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
Sicherheitsdaten
- wgk
- 3
- tsca
- No
- hs_code
- 2922504500
- risk_code
- 22-38-40-48/20/22
- safety_code
- 22-24/25
- Speicherklasse
- 11 - Combustible Solids
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.
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
Zugehörige Reaktionen
5
Notizen zur Verbindung
Wird geladen…