Metyrosine

HCID 441350CAS 672-87-7

基本情報

標準SMILES
C[C@](N)(Cc1ccc(O)cc1)C(=O)O
InChIKey
NHTGHBARYWONDQ-JTQLQIEISA-N
分子式
C10H13NO3
平均分子量
195.21 g/mol
単同位体質量
195.08954328

概要

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.

名称と識別子

優先名称
Metyrosine
IUPAC
(2S)-2-amino-3-(4-hydroxyphenyl)-2-methylpropanoic acid

名称と別名

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
名称をさらに表示
DTXSID6023315DOQ0J0TPF7CHEBI:6912L-588357-0DTXCID203315methyl-tyrosineRefChem:56543alpha-Methyltyrosine, (L)-

データベース識別子

CAS
672-87-7
PubChem CID
441350
DTXSID
DTXSID6023315
ChEMBL
CHEMBL1200862
ChEBI
CHEBI:6912
UNII
DOQ0J0TPF7
EC Number
211-599-5
Nikkaji
J9.465J

物性

構造計算による物性

XLogP
-1.6
極性表面積
83.6 Ų
水素結合供与体数
3
水素結合受容体数
4
回転可能結合数
3
重原子数
14

実験および物理化学的性質

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

Very slightly soluble

2.48e+00 g/L

Human Drugs · 2 件

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Melting Point312.5 °C
Physical DescriptionSolid

安全と法規制

GHS分類

GHS Classification · 4 件

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.

危険有害性情報

Hazard Classes and CategoriesAcute Tox. 4 (100%)

毒性情報

Drug Induced Liver Injury · 6 件

Drug Induced Liver Injury Rank (DILIrank 2.0)

Metyrosine

vNo-DILI-concern

0

No match

DOI:10.1016/j.drudis.2016.02.015

化学と産業

薬理情報

ATC Code · 2 件

C - Cardiovascular system

QC - Cardiovascular system

Pharmacodynamics · 1 件

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 件

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 件

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

関連反応

5 件

関連ノート

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