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Human Metabolome Database Version 3.5

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Showing metabocard for Methyldopa (HMDB11754)

Record Information
Version 3.5
Creation Date 2009-03-17 08:11:07 -0600
Update Date 2013-02-08 17:27:18 -0700
HMDB ID HMDB11754
Secondary Accession Numbers None
Metabolite Identification
Common Name Methyldopa
Description Methyldopa or alpha-methyldopa (brand names Aldomet, Apo-Methyldopa, Dopamet, Novomedopa) is a centrally-acting adrenergic antihypertensive medication. Its use is now deprecated following introduction of alternative safer classes of agents. However it continues to have a role in otherwise difficult to treat hypertension and gestational hypertension (formerly known as pregnancy-induced hypertension). Methyldopa is an aromatic-amino-acid decarboxylase inhibitor in animals and in man. Only methyldopa, the L-isomer of alpha-methyldopa, has the ability to inhibit dopa decarboxylase and to deplete animal tissues of norepinephrine. In man the antihypertensive activity appears to be due solely to the L-isomer. About twice the dose of the racemate (DL-alpha-methyldopa) is required for equal antihypertensive effect. Methyldopa has no direct effect on cardiac function and usually does not reduce glomerular filtration rate, renal blood flow, or filtration fraction. Cardiac output usually is maintained without cardiac acceleration. In some patients the heart rate is slowed. Normal or elevated plasma renin activity may decrease in the course of methyldopa therapy. Methyldopa reduces both supine and standing blood pressure. Methyldopa usually produces highly effective lowering of the supine pressure with infrequent symptomatic postural hypotension. Exercise hypotension and diurnal blood pressure variations rarely occur. Methyldopa, in its active metabolite form, is a central alpha-2 receptor agonist. Using methyldopa leads to alpha-2 receptor-negative feedback to sympathetic nervous system (SNS) (centrally and peripherally), allowing peripheral sympathetic nervous system tone to decrease. Such activity leads to a decrease in total peripheral resistance (TPR) and cardiac output. When introduced it was a mainstay of antihypertensive therapy, but its use has declined, with increased use of other safer classes of agents. One of its important present-day uses is in the management of pregnancy-induced hypertension, as it is relatively safe in pregnancy compared to other antihypertensive drugs (Wikipedia).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (-)-a-methyldopa
  2. (-)-alpha-methyldopa
  3. (-)-methyldopa
  4. (S)-(-)-a-methyldopa
  5. (S)-(-)-alpha-methyldopa
  6. 2-Methyl-3-(3,4-dihydroxyphenyl)alanine
  7. 3,4-Dihydroxy-2-methylphenylalanine (ACD/Name 4.0)
  8. a-Methyl dopa
  9. a-Methyl-L-3,4-dihydroxyphenylalanine
  10. a-Methyl-L-dopa
  11. a-Methyldopa (van)
  12. Aldoclor-150
  13. Aldoclor-250
  14. Aldomet
  15. Aldometil
  16. Aldoril 15
  17. Aldoril 25
  18. Aldoril D30
  19. Aldoril D50
  20. alpha Medopa
  21. alpha-Methyl dopa
  22. alpha-Methyl-L-3,4-dihydroxyphenylalanine
  23. alpha-Methyl-L-dopa
  24. alpha-Methyldopa (van)
  25. Alphamethyldopa
  26. AMD
  27. Apo Methyldopa Tab 125mg
  28. Apo Methyldopa Tab 250mg
  29. Apo Methyldopa Tab 500mg
  30. Apo-methyldopa
  31. Bayer 1440 L
  32. Baypresol
  33. Becanta
  34. Dopamet
  35. Dopamethyperpax
  36. Dopatec
  37. Dopegyt
  38. Grospisk
  39. Hyperpax
  40. Hypolag
  41. L(-)-a-Methylalanine
  42. L(-)-alpha-Methylalanine
  43. L-(-)-3-(3,4-Dihydroxyphenyl)-2-methyl-Alanine
  44. L-(-)-a-Methyl-a-methyl-Aldomin
  45. L-(-)-alpha-Methyl-alpha-methyl-Aldomin
  46. L-(a-MD)
  47. L-a-Methyl-(3, 4-dihydroxyphenyl)alanine
  48. L-a-Methyldopa
  49. L-alpha-Methyl-(3, 4-dihydroxyphenyl)alanine
  50. L-alpha-Methyldopa
  51. L-Methyl dopa
  52. Medomet
  53. Medopa
  54. Medopal
  55. Medopren
  56. Methoplain
  57. Methyldopa 125 Tab 125mg
  58. Methyldopa 250 Tab
  59. Methyldopa 500 Tab 500mg
  60. Methyldopa anhydrous
  61. Methyldopate
  62. Methyldopate HCL
  63. Novo-Medopa Tab 125mg
  64. Novo-Medopa Tab 250mg
  65. Novo-Medopa Tab 500mg
  66. Novomedopa
  67. Nu-medopa
  68. Nu-Medopa Tab 125mg
  69. Nu-Medopa Tab 250mg
  70. Nu-Medopa Tab 500mg
  71. Presinol
  72. Presolisin
  73. Sedometil
  74. Sembrina
Chemical Formula C10H13NO4
Average Molecular Weight 211.2145
Monoisotopic Molecular Weight 211.084457909
IUPAC Name (2S)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid
Traditional IUPAC Name methyldopa
CAS Registry Number 555-30-6
SMILES C[C@](N)(CC1=CC(O)=C(O)C=C1)C(O)=O
InChI Identifier InChI=1S/C10H13NO4/c1-10(11,9(14)15)5-6-2-3-7(12)8(13)4-6/h2-4,12-13H,5,11H2,1H3,(H,14,15)/t10-/m0/s1
InChI Key CJCSPKMFHVPWAR-JTQLQIEISA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Amino Acids and Derivatives
Sub Class Alpha Amino Acids and Derivatives
Other Descriptors
  • Aromatic Homomonocyclic Compounds
  • L-tyrosine derivative(ChEBI)
Substituents
  • 1,2 Diphenol
  • Amphetamine Or Derivative
  • Carboxylic Acid
  • Catecholamine
  • Phenethylamine
  • Phenol
  • Phenol Derivative
  • Primary Aliphatic Amine (Alkylamine)
Direct Parent Alpha Amino Acids and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 300 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 10mg/mL at 25 °C Not Available
LogP -1.79 MEYLAN,WM & HOWARD,PH (1995)
Predicted Properties
Property Value Source
Water Solubility 2.26 g/L ALOGPS
LogP -2.02 ALOGPS
LogP -1.4 ChemAxon
LogS -1.97 ALOGPS
pKa (strongest acidic) 1.73 ChemAxon
pKa (strongest basic) 9.85 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 4 ChemAxon
Polar Surface Area 103.78 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 53.79 ChemAxon
Polarizability 20.74 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Urine Detected and Quantified
Article_icon
0.5 (0.0-1.0) umol/mmol creatinine Adult (>18 years old) Both Prostate Cancer Estimated concentration
Associated Disorders and Diseases
Disease References
Prostate cancer
  • Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411 Link_out
    Associated OMIM IDs
    DrugBank ID Not Available
    Phenol Explorer Compound ID Not Available
    Phenol Explorer Metabolite ID Not Available
    FoodDB ID FDB028425
    KNApSAcK ID Not Available
    Chemspider ID 35562 Link_out
    KEGG Compound ID C07194 Link_out
    BioCyc ID ALPHA-METHYLDOPA Link_out
    BiGG ID Not Available
    Wikipedia Link Methyldopa Link_out
    NuGOwiki Link HMDB11754 Link_out
    Metagene Link HMDB11754 Link_out
    METLIN ID Not Available
    PubChem Compound 38853 Link_out
    PDB ID Not Available
    ChEBI ID 61058 Link_out
    References
    Synthesis Reference Not Available
    Material Safety Data Sheet (MSDS) Download (PDF)
    General References Not Available