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2D Structure
Also known as: 28860-95-9, Lodosyn, Carbidopa anhydrous, (s)-(-)-carbidopa, (s)-carbidopa, S-(-)-carbidopa
Molecular Formula
C10H14N2O4
Molecular Weight
226.23  g/mol
InChI Key
TZFNLOMSOLWIDK-JTQLQIEISA-N
FDA UNII
KR87B45RGH

An inhibitor of DOPA DECARBOXYLASE that prevents conversion of LEVODOPA to dopamine. It is used in PARKINSON DISEASE to reduce peripheral adverse effects of LEVODOPA. It has no anti-parkinson activity by itself.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2S)-3-(3,4-dihydroxyphenyl)-2-hydrazinyl-2-methylpropanoic acid
2.1.2 InChI
InChI=1S/C10H14N2O4/c1-10(12-11,9(15)16)5-6-2-3-7(13)8(14)4-6/h2-4,12-14H,5,11H2,1H3,(H,15,16)/t10-/m0/s1
2.1.3 InChI Key
TZFNLOMSOLWIDK-JTQLQIEISA-N
2.1.4 Canonical SMILES
CC(CC1=CC(=C(C=C1)O)O)(C(=O)O)NN
2.1.5 Isomeric SMILES
C[C@](CC1=CC(=C(C=C1)O)O)(C(=O)O)NN
2.2 Other Identifiers
2.2.1 UNII
KR87B45RGH
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Carbidopa, (r)-isomer

2. Carbidopa, (s)-isomer

3. Lodosin

4. Lodosyn

5. Methyldopahydrazine

6. Mk 485

7. Mk 486

8. Mk-485

9. Mk-486

10. Mk485

11. Mk486

2.3.2 Depositor-Supplied Synonyms

1. 28860-95-9

2. Lodosyn

3. Carbidopa Anhydrous

4. (s)-(-)-carbidopa

5. (s)-carbidopa

6. S-(-)-carbidopa

7. Alpha-methyldopahydrazine

8. L-alpha-methyldopahydrazine

9. N-aminomethyldopa

10. Carbidopum

11. Carbidopum [inn-latin]

12. Carbidopa (anhydrous)

13. S(-)-carbidopa

14. Mk 486

15. (2s)-3-(3,4-dihydroxyphenyl)-2-hydrazinyl-2-methylpropanoic Acid

16. Carbidopa [inn]

17. L-3-(3,4-dihydroxyphenyl)-2-methyl-2-hydrazinopropionic Acid

18. (2s)-3-(3,4-dihydroxyphenyl)-2-hydrazino-2-methylpropanoic Acid

19. (-)-l-alpha-hydrazino-3,4-dihydroxy-alpha-methylhydrocinnamic Acid

20. (s)-3-(3,4-dihydroxyphenyl)-2-hydrazinyl-2-methylpropanoic Acid

21. Kr87b45rgh

22. (alphas)-alpha-hydrazino-3,4-dihydroxy-alpha-methylbenzenepropanoic Acid

23. Chebi:39585

24. 28860-95-9 (anhydrous)

25. Ncgc00024596-05

26. Hadrazino-alpha-methyldopa

27. C-dopa

28. 3,3,3-trideuterio-2-[dideuterio-(3,4-dihydroxyphenyl)methyl]-2-hydrazinylpropanoic Acid

29. Smr000058235

30. Ccris 5093

31. Sr-01000597655

32. Einecs 249-271-9

33. Unii-kr87b45rgh

34. Benzenepropanoic Acid, .alpha.-hydrazino-3,4-dihydroxy-.alpha.-methyl-, (s)-

35. Alpha-hydrazino-alpha-methyl-beta-(3,4-dihydroxyphenyl)propionic Acid

36. L-alpha-methyl-alpha-hydrazino-beta-(3,4-dihydroxyphenylpropionic Acid

37. L-alpha-methyl-beta-(3,4-dihydroxyphenyl)-alpha-hydrazinopropionic Acid

38. Mfcd00069231

39. Nd0611

40. Tocris-0455

41. C-126

42. Dsstox_cid_2735

43. Carbidopa [who-dd]

44. Dsstox_rid_76707

45. Dsstox_gsid_22735

46. Lopac0_000382

47. Schembl35084

48. Mls000069628

49. Mls002207014

50. S-(-)-carbidopa Monohydrate

51. Gtpl5159

52. Carbidopa, L- Anhydrous

53. Carbidopa Anhydrous [mi]

54. Chembl1201236

55. Dtxsid4022735

56. Hms2089b12

57. Hms3266a20

58. Hms3411m13

59. Hms3655g20

60. Hms3675m13

61. Hms3713l10

62. Hms3884m14

63. Hy-b0311

64. Tox21_110910

65. (2s)-3-(3,4-dihydroxyphenyl)-2-hydrazino-2-methyl-propanoic Acid

66. Bdbm50418773

67. Nsc751137

68. S1891

69. Zinc19168887

70. Akos015969657

71. Benzenepropanoic Acid, Alpha-hydrazino-3,4-dihydroxy-alpha-methyl-, (s)-

72. Hydrocinnamic Acid, Alpha-hydrazino-3,4-dihydroxy-alpha-methyl-, L-

73. Ac-1676

74. Ccg-204476

75. Db00190

76. Sdccgmls-0072919.p025

77. Mls-0072919

78. Smp1_000057

79. Ncgc00024596-01

80. Ncgc00024596-03

81. Ncgc00024596-06

82. Ncgc00024596-07

83. Ncgc00024596-08

84. As-16862

85. Bc164279

86. Mls-0072919.p013

87. Cas-28860-95-9

88. Eu-0100382

89. Sw199080-2

90. 60c959

91. Ab00441332-05

92. Ab00441332-06

93. Ab00441332_07

94. Ab00441332_08

95. Sr-01000597655-1

96. Sr-01000597655-3

97. Sr-01000597655-5

98. Sr-01000597655-9

99. Brd-k78712176-001-07-5

100. Benzenepropanoic Acid, A-hydrazino-3,4-dihydroxy-a-methyl-

101. (-)-l-alpha-hydrazino-3,4-dihydroxy-alpha-methylhydrocinamic Acid

102. (s)-?-hydrazino-?-methyl-?-(3,4-dihydroxyphenyl)propionic Acid

103. (s)-3-(3,4-dihydroxyphenyl)-2-hydrazino-2-methylpropionic Acid

104. (s)-3-(3,4-dihydroxyphenyl)-2-hydrazinyl-2-methylpropanoicacid

105. (2s)-3-(3,4-dihydroxyphenyl)-2-hydrazinyl-2-methyl-propanoic Acid

106. (2s)-3-(3,4-dihydroxyphenyl)-2-hydrazino-2-methylpropionic Acid Monohydrate

107. Benzenepropanoic Acid, .alpha.-hydrazinyl-3,4-dihydroxy-.alpha.-methyl-, (.alpha.s)-

108. Kinson; 3-(3,4-dihydroxy-phenyl)-2-hydrazino-2-methyl-propionic Acid

109. 1426847-87-1

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 226.23 g/mol
Molecular Formula C10H14N2O4
XLogP3-2.2
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count6
Rotatable Bond Count4
Exact Mass226.09535693 g/mol
Monoisotopic Mass226.09535693 g/mol
Topological Polar Surface Area116 Ų
Heavy Atom Count16
Formal Charge0
Complexity261
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 4  
Drug NameCarbidopa
PubMed HealthCarbidopa (By mouth)
Drug ClassesAntiparkinsonian
Drug LabelCarbidopa and levodopa extended release tablets are extended release combination of carbidopa and levodopa for the treatment of Parkinsons disease and syndrome.Carbidopa, an inhibitor of aromatic amino acid decarboxylation, is a white, crystalline...
Active IngredientCarbidopa
Dosage FormTablet
RouteOral
Strength25mg
Market StatusPrescription
CompanyAmerigen Pharms

2 of 4  
Drug NameLodosyn
PubMed HealthCarbidopa (By mouth)
Drug ClassesAntiparkinsonian
Drug LabelCarbidopa, an inhibitor of aromatic amino acid decarboxylation, is a white, crystalline compound, slightly soluble in water, with a molecular weight of 244.3. It is designated chemically as ()-L--hydrazino--methyl--(3,4-dihydroxybenzene) pro...
Active IngredientCarbidopa
Dosage FormTablet
RouteOral
Strength25mg
Market StatusPrescription
CompanyAton

3 of 4  
Drug NameCarbidopa
PubMed HealthCarbidopa (By mouth)
Drug ClassesAntiparkinsonian
Drug LabelCarbidopa and levodopa extended release tablets are extended release combination of carbidopa and levodopa for the treatment of Parkinsons disease and syndrome.Carbidopa, an inhibitor of aromatic amino acid decarboxylation, is a white, crystalline...
Active IngredientCarbidopa
Dosage FormTablet
RouteOral
Strength25mg
Market StatusPrescription
CompanyAmerigen Pharms

4 of 4  
Drug NameLodosyn
PubMed HealthCarbidopa (By mouth)
Drug ClassesAntiparkinsonian
Drug LabelCarbidopa, an inhibitor of aromatic amino acid decarboxylation, is a white, crystalline compound, slightly soluble in water, with a molecular weight of 244.3. It is designated chemically as ()-L--hydrazino--methyl--(3,4-dihydroxybenzene) pro...
Active IngredientCarbidopa
Dosage FormTablet
RouteOral
Strength25mg
Market StatusPrescription
CompanyAton

4.2 Drug Indication

Carbidopa is indicated with [levodopa] for the treatment of symptoms of idiopathic Parkinson disease, postencephalitic parkinsonism and symptomatic parkinsonism followed by carbon monoxide or manganese intoxication. The combination therapy is administered for the reduction of [levodopa]-driven nausea and vomiting. The product of carbidopa should be used in patients where the combination therapy of carbidopa/[levodopa] provide less than the adequate daily dosage. As well carbidopa can be used in patients where the dosages of carbidopa and [levodopa] require individual titration.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

When mixed with [levodopa], carbidopa inhibits the peripheral conversion of [levodopa] to dopamine and the decarboxylation of [oxitriptan] to serotonin by aromatic L-amino acid decarboxylase. This results in an increased amount of [levodopa] and [oxitriptan] available for transport to the central nervous system. Carbidopa also inhibits the metabolism of [levodopa] in the GI tract, thus, increasing the bioavailability of [levodopa]. The presence of additional units of circulating [levodopa] can increase the effectiveness of the still functional dopaminergic neurons and it has been shown to alleviate symptoms for a time. The action of carbidopa is very important as [levodopa] is able to cross the blood-brain barrier while dopamine cannot. Hence the administration of carbidopa is essential to prevent the transformation of external [levodopa] to dopamine before reaching the main action site in the brain. The coadministration of carbidopa with [levodopa] has been shown to increase the half-life of [levodopa] more than 1.5 times while increasing the plasma level and decreasing clearance. The combination therapy has also shown an increase of the recovery of [levodopa] in urine instead of dopamine which proves a reduced metabolism. This effect has been highly observed by a significant reduction in [levodopa] requirements and a significant reduction in the presence of side effects such as nausea. It has been observed that the effect of carbidopa is not dose-dependent.


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.)


Aromatic Amino Acid Decarboxylase Inhibitors

Compounds and drugs that block or inhibit the enzymatic action of AROMATIC AMINO ACID DECARBOXYLASES. Pharmaceutical agents in this category are used in conjunction with LEVODOPA in order to slow its metabolism. (See all compounds classified as Aromatic Amino Acid Decarboxylase Inhibitors.)


Dopamine Agents

Any drugs that are used for their effects on dopamine receptors, on the life cycle of dopamine, or on the survival of dopaminergic neurons. (See all compounds classified as Dopamine Agents.)


5.3 Absorption, Distribution and Excretion

Absorption

When [levodopa]/carbidopa is administered orally, 40-70% of the administered dose is absorbed. Once absorbed, carbidopa shows bioavailability of 58%. A maximum concentration of 0.085 mcg/ml was achieved after 143 min with an AUC of 19.28 mcg.min/ml.


Route of Elimination

In animal studies, 66% of the administered dose of carbidopa was eliminated via the urine while 11% was found in feces. These studies were performed in humans and it was observed a urine excretion covering 50% of the administered dose.


Volume of Distribution

The volume of distribution reported for the combination therapy of carbidopa/[levodopa] is of 3.6 L/kg. However, carbidopa is widely distributed in the tissues, except in the brain. After one hour, carbidopa is found mainly in the kidney, lungs, small intestine and liver.


Clearance

The reported clearance rate for the combination therapy of [levodopa]/carbidopa is 51.7 L/h.


5.4 Metabolism/Metabolites

The loss of the hydrazine functional group (probably as molecular nitrogen) represents the major metabolic pathway for carbidopa. There are several metabolites of carbidopa metabolism including 3-(3,4-dihydroxyphenyl)-2-methylpropionic acid, 3-(4-hydroxy-3-methoxyphenyl)-2-methylpropionic acid, 3-(3-hydroxyphenyl)-2-methylpropionic acid, 3-(4-hydroxy-3-methoxyphenyl)-2-methyllactic acid, 3-(3-hydroxyphenyl)-2-methyllactic acid, and 3,4-dihydroxyphenylacetone (1,2).


5.5 Biological Half-Life

The reported half-life of carbidopa is of approximately 107 minutes.


5.6 Mechanism of Action

Carbidopa is an inhibitor of the DDC which in order, inhibits the peripheral metabolism of levodopa. DDC is very important in the biosynthesis of L-tryptophan to serotonin and the modification of L-DOPA to dopamine. DDC can be found in the body periphery and in the blood-brain barrier. The action of carbidopa is focused on peripheral DDC as this drug cannot cross the blood-brain barrier. Hence, it will prevent the metabolism of [levodopa] in the periphery but it will not have any activity on the generation of dopamine in the brain.