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Metirosine

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Metirosine
Skeletal formula
Ball-and-stick model of metirosine as a zwitterion
Clinical data
Trade names Demser
Other names Metyrosine (USAN US)
AHFS/Drugs.com Micromedex Detailed Consumer Information
License data
Pregnancy
category
  • C
ATC code
Legal status
Legal status
Pharmacokinetic data
Elimination half-life 3.4–3.7 hours
Identifiers
  • (2S)-2-amino- 3-(4-hydroxyphenyl)- 2-methylpropanoic acid
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.010.546
Chemical and physical data
Formula C10H13NO3
Molar mass 195.218 g·mol−1
3D model (JSmol)
  • O=C(O)[C@@](N)(Cc1ccc(O)cc1)C
  • 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 checkY
  • Key:NHTGHBARYWONDQ-JTQLQIEISA-N checkY
 ☒NcheckY (what is this?)  (verify)

Metirosine (INN and BAN; α-Methyltyrosine, Metyrosine USAN, AMPT) is an antihypertensive drug. It inhibits the enzyme tyrosine hydroxylase and, therefore, catecholamine synthesis, which, as a consequence, depletes the levels of the catecholamines dopamine, adrenaline and noradrenaline in the body.

It is available as a generic medication.

Clinical use

Metirosine has been shown to suppress catecholamine synthesis and alleviate symptoms related to catecholamine excess, including hypertension, headache, tachycardia, constipation, and tremor. Metirosine is primarily used to reduce these symptoms in patients with pheochromocytoma. It is contraindicated for the treatment of essential hypertension.

Metirosine is used as an off-label treatment for DiGeorge syndrome.

Metirosine is used in scientific research to investigate the effects of catecholamine depletion on behavior. There is evidence that catecholamine depletion causes an increase in sleepiness that is more pronounced than sleep deprivation, and that the fatigue lingers after the drug is discontinued. Catecholamine depletion has also been linked to a negative mood, though this is reported less often than sleepiness.

See also

External links

  • "Metyrosine". Drug Information Portal. U.S. National Library of Medicine.

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