Home > Compound List > Product Information
Metyrosine_Molecular_structure_CAS_672-87-7)
Click picture or here to close

Metyrosine

Catalog No. DB00765 Name DrugBank
CAS Number 672-87-7 Website http://www.ualberta.ca/
M. F. C10H13NO3 Telephone (780) 492-3111
M. W. 195.21512 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 645

SYNONYMS

IUPAC name
(2S)-2-amino-3-(4-hydroxyphenyl)-2-methylpropanoic acid
IUPAC Traditional name
metyrosine
Brand Name
Demser
Synonyms
Metirosine
Methyltyrosine

DATABASE IDS

PubChem SID 46506079
CAS Number 672-87-7
PubChem CID 441350

PROPERTIES

Hydrophobicity(logP) -1.7
Solubility Very slightly soluble

DETAILS

Description (English)
Item Information
Drug Groups approved
Description 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. (Martindale, The Extra Pharmacopoeia, 30th ed)
Indication For use in the treatment of patients with pheochromocytoma, for preoperative preparation of patients for surgery, management of patients when surgery is contraindicated, and chronic treatment of patients with malignant pheochromocytoma.
Pharmacology 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.
Toxicity Signs of metyrosine overdosage include those central nervous system effects observed in some patients even at low dosages. At doses exceeding 2000 mg/day, some degree of sedation or feeling of fatigue may persist. Doses of 2000-4000 mg/day can result in anxiety or agitated depression, neuromuscular effects (including fine tremor of the hands, gross tremor of the trunk, tightening of the jaw with trismus), diarrhea, and decreased salivation with dry mouth. The acute toxicity of metyrosine was 442 mg/kg and 752 mg/kg in the female mouse and rat respectively.
Affected Organisms
Humans and other mammals
Biotransformation Little biotransformation, with catechol metabolites accounting for less than 1% of the administered dose.
Absorption Well absorbed from the gastrointestinal tract.
Half Life 3.4 to 3.7 hours
Elimination 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.
External Links
RxList
Drugs.com

REFERENCES