Biology:Metirosine

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Short description: Chemical compound
Metirosine
Skeletal formula
Ball-and-stick model of metirosine as a zwitterion
Clinical data
Trade namesDemser
Other namesMetyrosine (USAN US)
AHFS/Drugs.comMicromedex Detailed Consumer Information
License data
Pregnancy
category
  • C
ATC code
Legal status
Legal status
Pharmacokinetic data
Elimination half-life3.4–3.7 hours
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
FormulaC10H13NO3
Molar mass195.218 g·mol−1
3D model (JSmol)
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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.[1]

Clinical use

Metirosine has been shown to suppress catecholamine synthesis and alleviate symptoms related to catecholamine excess, including hypertension, headache, tachycardia, constipation, and tremor.[2] Metirosine is primarily used to reduce these symptoms in patients with pheochromocytoma.[3] It is contraindicated for the treatment of essential hypertension.

Metirosine is used as an off-label treatment for DiGeorge syndrome.[4]

Metirosine is used in scientific research to investigate the effects of catecholamine depletion on behavior.[5] 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.[6]

See also

  • p-Chlorophenylalanine

References

  1. "Metyrosine: FDA-Approved Drugs". https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=213734. 
  2. Naruse, Mitsuhide; Satoh, Fumitoshi; Tanabe, Akiyo; Okamoto, Takahiro; Ichihara, Atsuhiro; Tsuiki, Mika; Katabami, Takuyuki; Nomura, Masatoshi et al. (2018). "Efficacy and safety of metyrosine in pheochromocytoma/paraganglioma: a multi-center trial in Japan". Endocrine Journal 65 (3): 359–371. doi:10.1507/endocrj.EJ17-0276. ISSN 0918-8959. PMID 29353821. 
  3. "Alpha-methyltyrosine in the management of phaeochromocytoma". Thorax 37 (8): 632–3. August 1982. doi:10.1136/thx.37.8.632. PMID 7179194. 
  4. "Doctors said the boy was suffering from teenage psychosis. What he really had was a rare genetic condition.". The Washington Post. 30 April 2021. https://www.washingtonpost.com/health/teenage-psychosis-genetic-condition/2021/04/30/65133794-6be5-11eb-9ead-673168d5b874_story.html. 
  5. O'Leary, OF; Bechtholt, AJ; Crowley, JJ; Hill, TE; Page, ME; Lucki, I (2007). "Depletion of serotonin and catecholamines block the acute behavioral response to different classes of antidepressant drugs in the mouse tail suspension test". Psychopharmacology 192 (3): 357–71. doi:10.1007/s00213-007-0728-9. PMID 17318507. 
  6. McCann, Una D.; Penetar, David M.; Shaham, Yavin; Thome, David R.; Sing, Helen C.; Thomas, Maria L.; Gillin, J. Christian; Belenky, Gregory (June 1993). "Effects of Catecholamine Depletion on Alertness and Mood in Rested and Sleep Deprived Normal Volunteers". Neuropsychopharmacology 8 (4): 345–356. doi:10.1038/npp.1993.34. ISSN 0893-133X. PMID 8099791. 

External links