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Details

Stereochemistry ABSOLUTE
Molecular Formula C10H13NO3
Molecular Weight 195.2151
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METYROSINE

SMILES

C[C@](N)(CC1=CC=C(O)C=C1)C(O)=O

InChI

InChIKey=NHTGHBARYWONDQ-JTQLQIEISA-N
InChI=1S/C10H13NO3/c1-10(11,9(13)14)6-7-2-4-8(12)5-3-7/h2-5,12H,6,11H2,1H3,(H,13,14)/t10-/m0/s1

HIDE SMILES / InChI

Description

Metirosine is an antihypertensive drug. 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. Metirosine is used for 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.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Demser

Cmax

ValueDoseCo-administeredAnalytePopulation
3313 ng/mL
230 mg 2 times / day steady-state, oral
METIROSINE plasma
Homo sapiens
6550 ng/mL
920 mg 1 times / day steady-state, oral
METIROSINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
15538 ng × h/mL
230 mg 2 times / day steady-state, oral
METIROSINE plasma
Homo sapiens
28005 ng × h/mL
920 mg 1 times / day steady-state, oral
METIROSINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
9.1 h
230 mg 2 times / day steady-state, oral
METIROSINE plasma
Homo sapiens
4.1 h
920 mg 1 times / day steady-state, oral
METIROSINE plasma
Homo sapiens

Doses

AEs

PubMed

Sample Use Guides

In Vivo Use Guide
The recommended initial dosage for adults and children 12 years of age and older is 250 mg orally four times daily. This may be increased by 250 mg to 500 mg every day to a maximum of 4.0 g/day in divided doses.
Route of Administration: Oral
In Vitro Use Guide
DA synthesis inhibition (Metirosine, 50 uM) resulted in a marked increase in the firing rates of mouse dopaminergic cells.