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    Chemistry

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    Also known as: 23651-95-8, L-dops, Dops, Northera, 3916-18-5, (2s,3r)-2-amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid
    Molecular Formula
    C9H11NO5
    Molecular Weight
    213.19  g/mol
    InChI Key
    QXWYKJLNLSIPIN-JGVFFNPUSA-N
    FDA UNII
    24A0V01WKS
    Droxidopa
    A synthetic precursor of norepinephrine that is used in the treatment of PARKINSONIAN DISORDERS and ORTHOSTATIC HYPOTENSION.
    The physiologic effect of droxidopa is by means of Increased Blood Pressure.
    1 2D Structure

    Droxidopa

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2S,3R)-2-amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid
    2.1.2 InChI
    InChI=1S/C9H11NO5/c10-7(9(14)15)8(13)4-1-2-5(11)6(12)3-4/h1-3,7-8,11-13H,10H2,(H,14,15)/t7-,8+/m0/s1
    2.1.3 InChI Key
    QXWYKJLNLSIPIN-JGVFFNPUSA-N
    2.1.4 Canonical SMILES
    C1=CC(=C(C=C1C(C(C(=O)O)N)O)O)O
    2.1.5 Isomeric SMILES
    C1=CC(=C(C=C1[C@H]([C@@H](C(=O)O)N)O)O)O
    2.2 Other Identifiers
    2.2.1 UNII
    24A0V01WKS
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 3,4 Dihydroxyphenylserine

    2. 3,4 Threo Dops

    3. 3,4-dihydroxyphenylserine

    4. 3,4-threo-dops

    5. Dl Threo 3,4 Dihydroxyphenylserine

    6. Dl-threo-3,4-dihydroxyphenylserine

    7. Droxidopa, (dl-tyr)-isomer

    8. Erythro 3,4 Dihydroxyphenylserine

    9. Erythro-3,4-dihydroxyphenylserine

    10. Threo Dops

    11. Threo-dops

    2.3.2 Depositor-Supplied Synonyms

    1. 23651-95-8

    2. L-dops

    3. Dops

    4. Northera

    5. 3916-18-5

    6. (2s,3r)-2-amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic Acid

    7. Dl-threo-droxidopa

    8. Dl-threo-3,4-dihydroxyphenylserine

    9. Dl-threo-dops

    10. Threo-dopaserine

    11. L-threodops

    12. L-threo-dops

    13. Dl-threo-dihydroxyphenylserine

    14. Threo-dihydroxyphenylserine

    15. Sm 5688

    16. Chebi:31524

    17. L-dihydroxyphenylserine

    18. Droxidopa (l-dops)

    19. Serine, 3-(3,4-dihydroxyphenyl)-, Dl-threo-

    20. L-threo-dihydroxyphenylserine

    21. 24a0v01wks

    22. J7a92w69l7

    23. Dl-threo-beta-(3,4-dihydroxyphenyl)serine

    24. Droxydopa

    25. L-threo-3,4-dihydroxyphenylserine

    26. Norethra

    27. Droxidopa [latin]

    28. Threo-beta,3-dihydroxy-dl-tyrosine

    29. Einecs 223-480-5

    30. Beta,3-dihydroxy-dl-tyrosine Threo-

    31. 3,4-dihydroxyphenylserine

    32. Brn 2852792

    33. Droxidopum

    34. L-tyrosine, Beta,3-dihydroxy-, Threo-

    35. Unii-24a0v01wks

    36. Dl-threo-3-(3,4-dihydroxyphenyl)serine

    37. Droxidopa [usan:inn:jan]

    38. Unii-j7a92w69l7

    39. (2rs,3rs)-2-amino-3-(3,4-dihydroxy-phenyl)-3-hydroxy-propionic Acid

    40. L-threo 3,4-dihydroxyphenylserine

    41. Northera (tn)

    42. L-threo Dops

    43. Dops (tn)

    44. L-threo-3-(3,4-dihydroxyphenyl)serine

    45. Dl-tyrosine, Beta,3-dihydroxy-, Threo-

    46. Droxidopa [inn]

    47. Droxidopa [jan]

    48. Droxidopa [mi]

    49. Threo-2-amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropionic Acid

    50. Droxidopa [usan]

    51. Dl-tyrosine, .beta.,3-dihydroxy-, Threo-

    52. Droxidopa [vandf]

    53. (-)-(2s,3r)-2-amino-3-hydroxy-3-(3,4-dihydroxyphenyl)propionic Acid

    54. Droxidopa [mart.]

    55. Droxidopa [who-dd]

    56. 1-14-00-00685 (beilstein Handbook Reference)

    57. 1260173-94-1

    58. Schembl134299

    59. Gtpl7391

    60. Droxidopa (jp17/usan/inn)

    61. Droxidopa [orange Book]

    62. Chembl2103827

    63. Dtxsid6046422

    64. Droxidopa (l-dops,sm-5688)

    65. Dtxsid201017236

    66. Bcp06516

    67. Zinc1482049

    68. Bdbm50103611

    69. Mfcd00799030

    70. S3041

    71. Sm5688

    72. (betar)-beta,3-dihydroxy-l-tyrosine

    73. L-dops, >=98% (hplc)

    74. (2s,3r)-3,4-dihydroxy-phenylserine

    75. Akos015889899

    76. Ccg-222060

    77. Db06262

    78. Sm-5688

    79. Ncgc00344531-04

    80. As-61328

    81. Hy-13458

    82. L-tyrosine, Beta,3-dihydroxy-, (betar)-

    83. D4235

    84. L-tyrosine, Beta,3-dihydroxy-, (beta-r)-

    85. Threo-3,4-dihydroxyphenylserine, L-

    86. 3,4-dihydroxyphenylserine-threo, Dl-

    87. Dl-threo- Beta -(3,4-dihydroxyphenyl)serine

    88. (-)-threo-3-(3,4-dihydroxyphenyl)-l-serine

    89. D01277

    90. D90266

    91. Serine, 3-(3,4-dihydroxyphenyl)-, L-threo-

    92. Ab01566868_01

    93. 916a185

    94. A816824

    95. Q907853

    96. Sr-01000883755

    97. Q-201050

    98. Sr-01000883755-1

    99. L-tyrosine, .beta.,3-dihydroxy-, (.beta.r)-

    100. D-tyrosine, .beta.,3-dihydroxy-, (.beta.s)-rel-

    101. 23651-95-8,1260173-94-1(hcl)

    102. (2s,3r)-2-amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropionic Acid

    103. (2s,3r)-3-(3,4-dihydroxyphenyl)-2-amino-3-hydroxypropanoic Acid

    104. (-)-(2s,3r)-2-amino-3-hydroxy-3-(3,4-dihydroxyphenyl)propanoic Acid

    105. (2rs,3rs)-2-amino-3-(3,4-dihydroxyphenyl)-3-hydroxy-propanoic Acid

    106. (-)-(2s,3r)-2-amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic Acid

    2.4 Create Date
    2005-08-08
    3 Chemical and Physical Properties
    Molecular Weight 213.19 g/mol
    Molecular Formula C9H11NO5
    XLogP3-3.2
    Hydrogen Bond Donor Count5
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count3
    Exact Mass213.06372245 g/mol
    Monoisotopic Mass213.06372245 g/mol
    Topological Polar Surface Area124 Ų
    Heavy Atom Count15
    Formal Charge0
    Complexity235
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    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 NameNorthera
    PubMed HealthDroxidopa (Oral route)
    Drug ClassesAdrenergic, Vasopressor
    Drug LabelNORTHERA capsules contain droxidopa, which is a synthetic amino acid precursor of norepinephrine, for oral administration. Chemically, droxidopa is ()-threo-3-(3,4-Dihydroxyphenyl)-L-serine. It has the following structural formula:Droxidopa is...
    Active IngredientDroxidopa
    Dosage FormCapsule
    RouteOral
    Strength200mg; 300mg; 100mg
    Market StatusPrescription
    CompanyLundbeck Na

    2 of 2  
    Drug NameNorthera
    PubMed HealthDroxidopa (Oral route)
    Drug ClassesAdrenergic, Vasopressor
    Drug LabelNORTHERA capsules contain droxidopa, which is a synthetic amino acid precursor of norepinephrine, for oral administration. Chemically, droxidopa is ()-threo-3-(3,4-Dihydroxyphenyl)-L-serine. It has the following structural formula:Droxidopa is...
    Active IngredientDroxidopa
    Dosage FormCapsule
    RouteOral
    Strength200mg; 300mg; 100mg
    Market StatusPrescription
    CompanyLundbeck Na

    4.2 Drug Indication

    For treatment of neurogenic orthostatic hypotension (NOH) associated with various disorders including Multiple System Atrophy, Familial Amyloid Polyneuropathy, hemodialysis induced hypotension and Parkinson's Disease. Also investigated for use/treatment in neurologic disorders, nephropathy, blood (blood forming organ disorders, unspecified), and dizzy/fainting spells.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Droxidopa is an orally active synthetic precursor of norepinephrine that increases the deficient supply of norepinephrine in patients with NOH, thereby improving orthostatic blood pressure and alleviating associated symptoms of lightheadedness, dizziness, blurred vision, and syncope through the induction of tachycardia (increased heart rate) and hypertension.

    5.2 MeSH Pharmacological Classification

    Antiparkinson Agents

    Agents used in the treatment of Parkinson's disease. The most commonly used drugs act on the dopaminergic system in the striatum and basal ganglia or are centrally acting muscarinic antagonists. (See all compounds classified as Antiparkinson Agents.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    DROXIDOPA
    5.3.2 FDA UNII
    J7A92W69L7
    5.3.3 Pharmacological Classes
    Increased Blood Pressure [PE]; Catecholamines [CS]
    5.4 ATC Code

    C - Cardiovascular system

    C01 - Cardiac therapy

    C01C - Cardiac stimulants excl. cardiac glycosides

    C01CA - Adrenergic and dopaminergic agents

    C01CA27 - Droxidopa

    5.5 Absorption, Distribution and Excretion

    Absorption

    Oral bioavailability is 90%.

    Route of Elimination

    Droxidopa is mainly excreted in the urine, with the main metabolite being 3-O-methyldihydroxyphenylserine.

    5.6 Metabolism/Metabolites

    Droxidopa is metabolized by aromatic L-amino acid decarboxylase.

    5.7 Biological Half-Life

    2-3 hours.

    5.8 Mechanism of Action

    Droxidopa crosses the blood-brain barrier where it is converted to norepinephrine via decarboxylation by L-aromatic-amino-acid decarboxylase. Norephinephrine acts at alpha-adrenergic receptors as a vasoconstrictor and at beta-adrenergic receptors as a heart stimulator and artery dilator.

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