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Technical details about Droxidopa, learn more about the structure, uses, toxicity, action, side effects and more

Droxidopa

Synopsis, Chemistry

APIs // Active Pharmaceutical Ingredients

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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

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

2D Structure

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 Formula	C₉H₁₁NO₅
Molecular Weight	213.19 g/mol
XLogP3	-3.2
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	3
Exact Mass	213.06372245 g/mol
Monoisotopic Mass	213.06372245 g/mol
Topological Polar Surface Area	124 Å²
Heavy Atom Count	15
Formal Charge	0
Complexity	235
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Northera
PubMed Health	Droxidopa (Oral route)
Drug Classes	Adrenergic, Vasopressor
Drug Label	NORTHERA 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 Ingredient	Droxidopa
Dosage Form	Capsule
Route	Oral
Strength	200mg; 300mg; 100mg
Market Status	Prescription
Company	Lundbeck Na

2 of 2
Drug Name	Northera
PubMed Health	Droxidopa (Oral route)
Drug Classes	Adrenergic, Vasopressor
Drug Label	NORTHERA 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 Ingredient	Droxidopa
Dosage Form	Capsule
Route	Oral
Strength	200mg; 300mg; 100mg
Market Status	Prescription
Company	Lundbeck 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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