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Chemistry

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Also known as: 672-87-7, Alpha-methyl-l-tyrosine, Metirosine, Demser, Methyltyrosine, (s)-alpha-methyltyrosine
Molecular Formula
C10H13NO3
Molecular Weight
195.21  g/mol
InChI Key
NHTGHBARYWONDQ-JTQLQIEISA-N
FDA UNII
DOQ0J0TPF7

Methyltyrosine
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)
Metyrosine is a Catecholamine Synthesis Inhibitor. The mechanism of action of metyrosine is as a Catecholamine Synthesis Inhibitor.
1 2D Structure

Methyltyrosine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2S)-2-amino-3-(4-hydroxyphenyl)-2-methylpropanoic acid
2.1.2 InChI
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
2.1.3 InChI Key
NHTGHBARYWONDQ-JTQLQIEISA-N
2.1.4 Canonical SMILES
CC(CC1=CC=C(C=C1)O)(C(=O)O)N
2.1.5 Isomeric SMILES
C[C@](CC1=CC=C(C=C1)O)(C(=O)O)N
2.2 Other Identifiers
2.2.1 UNII
DOQ0J0TPF7
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Alpha Methyl P Tyrosine

2. Alpha Methyl Para Tyrosine

3. Alpha Methyltyrosine

4. Alpha Methyltyrosine Hydrochloride

5. Alpha Mpt

6. Alpha-methyl- Dl-tyrosine

7. Alpha-methyl-p-tyrosine

8. Alpha-methyl-para-tyrosine

9. Alpha-methyltyrosine

10. Alpha-methyltyrosine Hydrochloride

11. Alpha-methyltyrosine, (+,-)-isomer

12. Alpha-methyltyrosine, (d,l)-isomer

13. Alpha-methyltyrosine, (l)-isomer

14. Alpha-mpt

15. Demser

16. Dl-tyrosine, Alpha-methyl-

17. Hydrochloride, Alpha-methyltyrosine

18. Metirosine

19. Racemetirosine

2.3.2 Depositor-Supplied Synonyms

1. 672-87-7

2. Alpha-methyl-l-tyrosine

3. Metirosine

4. Demser

5. Methyltyrosine

6. (s)-alpha-methyltyrosine

7. (s)-2-amino-3-(4-hydroxyphenyl)-2-methylpropanoic Acid

8. L-alpha-methyltyrosine

9. L-alpha-methyl-p-tyrosine

10. Metirosinum

11. Metirosina

12. Alpha-methyltyrosine

13. Alpha-methyl-l-p-tyrosine

14. (2s)-2-amino-3-(4-hydroxyphenyl)-2-methylpropanoic Acid

15. (-)-alpha-methyl-l-tyrosine

16. Mk-781

17. Metirosine [inn]

18. Racemetirosine, (s)-

19. Alpha-methyl-para-tyrosine

20. Doq0j0tpf7

21. Alpha-methyl-l-tyr

22. Chebi:6912

23. L-588357-0

24. Ncgc00094144-03

25. Dsstox_cid_3315

26. L-2-methyl-3-(4-hydroxyphenyl)alanine

27. Dsstox_rid_76972

28. Dsstox_gsid_23315

29. Mfcd00064201

30. Alpha-mpt

31. Cas-672-87-7

32. Metyrosine [usan]

33. (r)-alpha-methyltyrosine

34. Alpha-methyl-paratyrosine

35. Metyrosine [usan:usp]

36. Metirosinum [inn-latin]

37. Unii-doq0j0tpf7

38. Mk 781

39. Metirosina [inn-spanish]

40. L-2-me-tyr-oh

41. Metyrosine (usp)

42. Einecs 211-599-5

43. Demser (tn)

44. A-methyl-l-p-tyrosine

45. Metyrosine [mi]

46. Metirosine (jan/inn)

47. Metirosine [jan]

48. Spectrum3_001846

49. Metyrosine [vandf]

50. H-(me)tyr-oh

51. A-methyl-l-tyrosine

52. Metirosine [mart.]

53. (s)-2-(4-hydroxybenzyl)-2-aminopropanoic Acid

54. Metirosine [who-dd]

55. Metyrosine [usp-rs]

56. Lopac0_000811

57. Schembl50398

58. Bspbio_003232

59. Zinc693

60. Spectrum2300312

61. A-methyltyrosinea-methyltyrosine

62. Gtpl6956

63. L 588357-0

64. Chembl1200862

65. Dtxsid6023315

66. Metyrosine [orange Book]

67. Kbio3_002732

68. (-)-(s)-2-amino-3-(4-hydroxyphenyl)-2-methylpropionsaeure

69. Hms3262d03

70. Metyrosine [usp Monograph]

71. L-tyrosine, Alpha-methyl-, (-)-

72. Tox21_111253

73. Tox21_500811

74. S5797

75. Akos016844271

76. Tox21_111253_1

77. Ab02561

78. Am83582

79. Ccg-204895

80. Cs-w015723

81. Db00765

82. Hy-w015007

83. Lp00811

84. Sdccgsbi-0050788.p002

85. (-)-.alpha.-methyl-l-tyrosine

86. Ncgc00015701-06

87. Ncgc00094144-01

88. Ncgc00094144-04

89. Ncgc00094144-05

90. Ncgc00094144-06

91. Ncgc00094144-07

92. Ncgc00094144-11

93. Ncgc00261496-01

94. Ac-32982

95. Alpha-methyl-l-tyrosine, >=98% (tlc)

96. As-47139

97. Eu-0100811

98. L-tyrosine, .alpha.-methyl-, (-)-

99. C07921

100. D00762

101. F12275

102. M 8131

103. 672m877

104. A835693

105. Q6824116

106. (s)-2-amino-3-(4-hydroxyphenyl)-2-methylpropanoicacid

107. Z1617901128

108. (2s)-2-amino-3-(4-hydroxyphenyl)-2-methyl-propanoic Acid

109. (s)-a-methyl-4-hydroxy Phenylalanine, (s)-a-methyltyrosine

110. Metyrosine, United States Pharmacopeia (usp) Reference Standard

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 195.21 g/mol
Molecular Formula C10H13NO3
XLogP3-1.6
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count4
Rotatable Bond Count3
Exact Mass195.08954328 g/mol
Monoisotopic Mass195.08954328 g/mol
Topological Polar Surface Area83.6 Ų
Heavy Atom Count14
Formal Charge0
Complexity211
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameDemser
PubMed HealthMetyrosine (By mouth)
Drug ClassesAntihypertensive
Drug LabelDEMSERRegistered trademark of ATON PHARMA, INC.COPYRIGHT 2007 ATON PHARMA, INC.All rights reserved (Metyrosine) is ()--methyl-L-tyrosine or (-MPT). It has the following structural formula:Metyrosine is a white, crystalline compound of molec...
Active IngredientMetyrosine
Dosage FormCapsule
RouteOral
Strength250mg
Market StatusPrescription
CompanyAton Pharma Vpna

2 of 2  
Drug NameDemser
PubMed HealthMetyrosine (By mouth)
Drug ClassesAntihypertensive
Drug LabelDEMSERRegistered trademark of ATON PHARMA, INC.COPYRIGHT 2007 ATON PHARMA, INC.All rights reserved (Metyrosine) is ()--methyl-L-tyrosine or (-MPT). It has the following structural formula:Metyrosine is a white, crystalline compound of molec...
Active IngredientMetyrosine
Dosage FormCapsule
RouteOral
Strength250mg
Market StatusPrescription
CompanyAton Pharma Vpna

4.2 Drug 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.


5 Pharmacology and Biochemistry
5.1 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.


5.2 MeSH Pharmacological Classification

Enzyme Inhibitors

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
METYROSINE
5.3.2 FDA UNII
DOQ0J0TPF7
5.3.3 Pharmacological Classes
Catecholamine Synthesis Inhibitors [MoA]; Catecholamine Synthesis Inhibitor [EPC]
5.4 ATC Code

C - Cardiovascular system

C02 - Antihypertensives

C02K - Other antihypertensives

C02KB - Tyrosine hydroxylase inhibitors

C02KB01 - Metirosine


5.5 Absorption, Distribution and Excretion

Absorption

Well absorbed from the gastrointestinal tract.


Route of 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.


5.6 Metabolism/Metabolites

Little biotransformation, with catechol metabolites accounting for less than 1% of the administered dose.


5.7 Biological Half-Life

3.4 to 3.7 hours


5.8 Mechanism of Action

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.


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