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{{Drugbox
| Verifiedfields = changed
| verifiedrevid = 462251779
| IUPAC_name = (2''S'')-2-amino- 3-(4-hydroxyphenyl)- 2-methylpropanoic acid
| image = Metirosine.png


{{drugbox | IUPAC_name = 2-amino-3-(4-hydroxyphenyl)-2-methyl-propanoic acid | image = Metirosine.png | CAS_number = 672-87-7 | ATC_prefix = C02 | ATC_suffix = KB01 | ATC_supplemental =  | PubChem = 10123 | DrugBank =  | C=10 | H=13 | N=1 | O=3  | molecular_weight = 195.215 | bioavailability =  | protein_bound =  | metabolism =  | elimination_half-life = 3.4 - 3.7 hours | pregnancy_category =  | legal_status =  | routes_of_administration =  }}
<!--Clinical data-->
| tradename = Demser
| Drugs.com = {{drugs.com|CDI|metyrosine}}
| pregnancy_category =   
| legal_status =   
| routes_of_administration =   


{{SI}}
<!--Pharmacokinetic data-->
| bioavailability = 
| protein_bound = 
| metabolism = 
| elimination_half-life = 3.4–3.7 hours


==Mechanism of action==  
<!--Identifiers-->
'''Metirosine''' is an [[antihypertensive]] drug. It inhibits the enzyme [[tyrosine hydroxylase]] and, therefore, [[catecholamine]] synthesis.  
| CASNo_Ref = {{cascite|correct|CAS}}
==Clinical Use==  
| CAS_number_Ref = {{cascite|correct|??}}
Metirosine is used in the treatment of [[phaeochromocytoma]]. It is contra-indicated for the treatment of [[essential hypertension]]. 
| CAS_number = 672-87-7
| ATC_prefix = C02
| ATC_suffix = KB01
| ATC_supplemental =  
| PubChem = 10123
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00765
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 390103
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = DOQ0J0TPF7
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00762
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1200862


{{Antihypertensives and diuretics}}
<!--Chemical data-->
| C=10 | H=13 | N=1 | O=3
| molecular_weight = 195.215 g/mol
| smiles = O=C(O)[C@@](N)(Cc1ccc(O)cc1)C
| InChI = 1/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
| InChIKey = NHTGHBARYWONDQ-JTQLQIEIBZ
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = NHTGHBARYWONDQ-JTQLQIEISA-N
}}
 
'''Metirosine''' ([[International Nonproprietary Name|INN]] and [[British Approved Name|BAN]]; '''α-Methyltyrosine''', '''Metyrosine''' [[United States Adopted Name|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.
 
==Clinical Use==
Metirosine has been used in the treatment of [[pheochromocytoma]].<ref name="pmid7179194">{{cite journal |author=Green KN, Larsson SK, Beevers DG, Bevan PG, Hayes B |title=Alpha-methyltyrosine in the management of phaeochromocytoma |journal=Thorax |volume=37 |issue=8 |pages=632–3 |date=August 1982 |pmid=7179194 |pmc=459390 |doi= 10.1136/thx.37.8.632|url=}}</ref> It is contra-indicated for the treatment of [[essential hypertension]].
 
However it is now rarely used in medicine, its primary use being in scientific research to investigate the effects of catecholamine depletion on behaviour.<ref>O'Leary OF, Bechtholt AJ, Crowley JJ, Hill TE, Page ME, Lucki I. Depletion of serotonin and catecholamines block the acute behavioral response to different classes of antidepressant drugs in the mouse tail suspension test. ''Psychopharmacology (Berlin)''. 2007 Jun;192(3):357-71. PMID 17318507</ref>
 
==Chemistry==
Metyrosine, (−)α-methyltyrosine, is synthesized in a few different ways, the simplest of which is the synthesis from 4-methoxy[[phenylacetone]], which is reacted with [[potassium cyanide]] in the presence of [[ammonium carbonate]] to give the [[hydantoin]]. Treating this with [[hydrogen iodide]] removes the methyl-protecting group on the phenyl hydroxyl group and the product is hydrolyzed by [[barium hydroxide]] into a [[racemic]] mixture of α-methyl-D,L-tyrosine, from which the desired L-isomer is isolated.
 
==References==
{{reflist|2}}
 
{{Antihypertensives and diuretics}}
{{Enzyme inhibition}}


[[Category:Antihypertensive agents]]
[[Category:Antihypertensive agents]]
{{WH}}
[[Category:Cardiovascular Drugs]]
{{WikiDoc Sources}}
[[Category:Drug]]
[[Category:Vasodilators]]

Revision as of 00:27, 25 July 2014

Metirosine
Clinical data
Trade namesDemser
AHFS/Drugs.comConsumer Drug Information
ATC code
Pharmacokinetic data
Elimination half-life3.4–3.7 hours
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC10H13NO3
Molar mass195.215 g/mol
3D model (JSmol)
 ☒N☑Y (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.

Clinical Use

Metirosine has been used in the treatment of pheochromocytoma.[1] It is contra-indicated for the treatment of essential hypertension.

However it is now rarely used in medicine, its primary use being in scientific research to investigate the effects of catecholamine depletion on behaviour.[2]

Chemistry

Metyrosine, (−)α-methyltyrosine, is synthesized in a few different ways, the simplest of which is the synthesis from 4-methoxyphenylacetone, which is reacted with potassium cyanide in the presence of ammonium carbonate to give the hydantoin. Treating this with hydrogen iodide removes the methyl-protecting group on the phenyl hydroxyl group and the product is hydrolyzed by barium hydroxide into a racemic mixture of α-methyl-D,L-tyrosine, from which the desired L-isomer is isolated.

References

  1. ↑ Green KN, Larsson SK, Beevers DG, Bevan PG, Hayes B (August 1982). "Alpha-methyltyrosine in the management of phaeochromocytoma". Thorax. 37 (8): 632–3. doi:10.1136/thx.37.8.632. PMC 459390. PMID 7179194.
  2. ↑ O'Leary OF, Bechtholt AJ, Crowley JJ, Hill TE, Page ME, Lucki I. Depletion of serotonin and catecholamines block the acute behavioral response to different classes of antidepressant drugs in the mouse tail suspension test. Psychopharmacology (Berlin). 2007 Jun;192(3):357-71. PMID 17318507

Template:Enzyme inhibition

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