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Also known as: 638-23-3, S-carboxymethyl-l-cysteine, Carbocisteine, Carbocistein, S-(carboxymethyl)-l-cysteine, Mucodyne
Molecular Formula
C5H9NO4S
Molecular Weight
179.20  g/mol
InChI Key
GBFLZEXEOZUWRN-VKHMYHEASA-N
FDA UNII
740J2QX53R

Carbocisteine
A compound formed when iodoacetic acid reacts with sulfhydryl groups in proteins. It has been used as an anti-infective nasal spray with mucolytic and expectorant action.
1 2D Structure

Carbocisteine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2R)-2-amino-3-(carboxymethylsulfanyl)propanoic acid
2.1.2 InChI
InChI=1S/C5H9NO4S/c6-3(5(9)10)1-11-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m0/s1
2.1.3 InChI Key
GBFLZEXEOZUWRN-VKHMYHEASA-N
2.1.4 Canonical SMILES
C(C(C(=O)O)N)SCC(=O)O
2.1.5 Isomeric SMILES
C([C@@H](C(=O)O)N)SCC(=O)O
2.2 Other Identifiers
2.2.1 UNII
740J2QX53R
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 3-(carboxymethylthio)alanine

2. Carbocysteine, L Isomer

3. Carbocysteine, L-isomer

4. L-isomer Carbocysteine

5. Mucodine

6. Mucodyne

7. Mukodin

8. Rhinathiol

9. S Carboxymethylcysteine

10. S-(carboxymethyl)-l-cysteine

11. S-carboxymethylcysteine

12. Thiodril

2.3.2 Depositor-Supplied Synonyms

1. 638-23-3

2. S-carboxymethyl-l-cysteine

3. Carbocisteine

4. Carbocistein

5. S-(carboxymethyl)-l-cysteine

6. Mucodyne

7. Reomucil

8. Rhinathiol

9. Transbronchin

10. Lisomucil

11. Muciclar

12. Mucolase

13. Mucocis

14. Siroxyl

15. Loviscol

16. Mucofan

17. Bronchokod

18. Carbocit

19. Mucopront

20. Mucotab

21. Pectox

22. Lisil

23. Pectdrill

24. L-carbocisteine

25. H-cys(carboxymethyl)-oh

26. (r)-s-(carboxymethyl)cysteine

27. 186537-58-6

28. Carbocisteina

29. Carbocisteinum

30. Mucolex

31. Pulmoclase

32. Rinatiol

33. L-carbocysteine

34. S-(carboxymethyl)-(r)-cysteine

35. L-3-((carboxymethyl)thio)alanine

36. Superthiol Sirup

37. Thiodril

38. Lj 206

39. Methista

40. (l)-2-amino-3-(carboxymethylthio)propionic Acid

41. S-carboxymethylcysteine

42. Carbocisteine [inn]

43. 3-(carboxymethylthio)-l-alanine

44. R05cb03

45. Ahr 3053

46. Ahr-3053

47. Df 1794y

48. Nsc 14156

49. (2r)-2-amino-3-(carboxymethylsulfanyl)propanoic Acid

50. (2r)-2-amino-3-[(carboxymethyl)sulfanyl]propanoic Acid

51. L-cysteine, S-(carboxymethyl)-

52. Chembl396416

53. Chebi:16163

54. 740j2qx53r

55. Lj-206

56. Nsc-14156

57. Carbocysteine [usan]

58. Alanine, 3-((carboxymethyl)thio)-, L-

59. Chilvax

60. Mucosol

61. Carboxymethylated Cysteine

62. S-carboxylmethyl-l-cysteine

63. Broncodeterge

64. 1391068-19-1

65. Mucotron

66. Mukinyl

67. 3-((carboxymethyl)thio)-l-alanine

68. Mucojet Sirup

69. Mucolex Sirup

70. L-(carboxymethyl)cysteine

71. Scmc

72. (r)-2-amino-3-(carboxymethylthio)propanoic Acid

73. 3-((carboxymethyl)thio)alanine

74. 3-[(carboxymethyl)thio]alanine

75. Carbocisteinum [inn-latin]

76. Carbocisteina [inn-spanish]

77. Unii-740j2qx53r

78. Carbocysteine [usan:inn:ban]

79. L.j.206

80. (2r)-2-azaniumyl-3-(carboxylatomethylsulfanyl)propanoate

81. Mucodyne (tn)

82. Einecs 211-327-5

83. Carbocistein [jan]

84. Mfcd00002614

85. Carbocysteine Dl-form

86. Brn 1725012

87. L.j. 206

88. Carbocysteine [mi]

89. L-carbocisteine (jp17)

90. Carbocisteine [jan]

91. Carbocysteine [inci]

92. Schembl20854

93. (2r)-2-amino-3-(carboxymethylthio)propanoic Acid

94. Carbocisteine [mart.]

95. L-carbocisteine [jan]

96. Hy-d0205a

97. (carboxymethyl)cysteine-, (l)-

98. Dtxsid30110060

99. L-carbocisteine [who-dd]

100. 3-(carboxymethylthio)alanine, L-

101. S-carboxymethyl-l-cysteine, 98%

102. Zinc1529732

103. Carbocisteine [ep Monograph]

104. Bdbm50213735

105. S5216

106. Akos015922826

107. 5-amino-3-thiadihexanoic Acid, (l)-

108. Db04339

109. Ac-11146

110. As-57938

111. Cs-0017457

112. C-1850

113. C03727

114. D00175

115. H11928

116. (2r)-2-amino-3-(carboxymethylthio)propionic Acid

117. A813055

118. A816956

119. A834542

120. Q423408

121. 2-amino-3-(carboxymethylthio)propionic Acid, (l)-

122. Q-200796

123. (2r)-3-(carboxythio)-2-(methylamino)propanoic Acid

124. (2r)-2-amino-3-((carboxymethyl)thio)propionic Acid

125. (2r)-2-azanyl-3-(2-hydroxy-2-oxoethylsulfanyl)propanoic Acid

126. Carbocisteine, European Pharmacopoeia (ep) Reference Standard

127. (2r)-2-amino-3-[(carboxymethyl)sulfanyl]propanoic Acids-(carboxymethyl)-l-cysteine

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 179.20 g/mol
Molecular Formula C5H9NO4S
XLogP3-3.1
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count6
Rotatable Bond Count5
Exact Mass179.02522894 g/mol
Monoisotopic Mass179.02522894 g/mol
Topological Polar Surface Area126 Ų
Heavy Atom Count11
Formal Charge0
Complexity161
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 Indication

Carbocisteine is indicated over the counter and in prescription formulas to clear airway secretions in conditions associated with increased mucus.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Due to its mucolytic effects, carbocisteine significantly reduces sputum viscosity, cough, dyspnea and fatigue. Additionally, it prevents pulmonary infections by decreasing accumulated mucus in the respiratory tract; this is especially beneficial in preventing exacerbations of COPD caused by bacteria and viruses. It has in-vitro anti-inflammatory activity with some demonstrated action against free radicals.


5.2 MeSH Pharmacological Classification

Anti-Infective Agents, Local

Substances used on humans and other animals that destroy harmful microorganisms or inhibit their activity. They are distinguished from DISINFECTANTS, which are used on inanimate objects. (See all compounds classified as Anti-Infective Agents, Local.)


Expectorants

Agents that increase mucous excretion. Mucolytic agents, that is drugs that liquefy mucous secretions, are also included here. (See all compounds classified as Expectorants.)


5.3 ATC Code

R05CB03

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


R - Respiratory system

R05 - Cough and cold preparations

R05C - Expectorants, excl. combinations with cough suppressants

R05CB - Mucolytics

R05CB03 - Carbocisteine


5.4 Absorption, Distribution and Excretion

Absorption

Carbocisteine is rapidly absorbed in the gastrointestinal tract when taken orally with peak serum concentrations achieved within 1 to 1.7 hours.


Route of Elimination

About 30% to 60% of an orally administered dose is detected unchanged in the urine.


Volume of Distribution

Carbocisteine penetrates well into the lung and bronchial secretions.


Clearance

Clearance information for carbocisteine is not readily available in the literature.


5.5 Metabolism/Metabolites

Metabolic pathways for carbocisteine include acetylation, decarboxylation, and sulfoxidation, leading to the formation of pharmacologically inactive carbocisteine derivatives. Significant variability exists in metabolism due to genetic polymorphism in sulfoxidation capacity. Two cytosolic enzymes are responsible for the metabolism of carbocisteine: cysteine dioxygenase and phenylalanine 4-hydroxylase. Reduced metabolism can cause increased exposure to carbocisteine, explaining variable clinical response between patients who may polymorphisms affecting the enzymes responsible for carbocisteine metabolism. It is generally accepted that sulfodixation is the main metabolic pathway of carbocisteine, however, one group of researchers found a novel urinary metabolite, S-(carboxymethylthio)-L-cysteine (CMTC). No cysteinyl sulfoxide metabolites were found in the urine of patients taking carbocisteine in this study.


5.6 Biological Half-Life

The plasma half-life of carbicostine is 1.33 hours.


5.7 Mechanism of Action

The hypersecretion of mucus characterizes serious respiratory conditions including asthma, cystic fibrosis (CF), and chronic obstructive pulmonary disease (COPD). It blocks bacterial adherence to cells, preventing pulmonary infections. Glycoproteins (fucomucins, sialomucins and sulfomucins) regulate the viscoelastic properties of bronchial mucus. Increased fucomucins can be found in the mucus of patients with COPD. Carbocisteine serves to restore equilibrium between sialomucins and fucomucins, likely by intracellular stimulation of sialyl transferase enzyme, thus reducing mucus viscosity. A study found that L-carbocisteine can inhibit damage to cells by hydrogen peroxide (H2O2) by activating protein kinase B (Akt) phosphorylation, suggesting that carbocisteine may have antioxidant effects and prevent apoptosis of lung cells. There is some evidence that carbocisteine suppresses NF-B and ERK1/2 MAPK signalling pathways, reducing TNF-alpha induced inflammation in the lungs, as well as other inflammatory pathways. An in-vitro study found that L-carbocisteine reduces intracellular adhesion molecule 1 (ICAM-1), inhibiting rhinovirus 14 infection, thereby reducing airway inflammation.


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11-Jan-2021
30-Sep-2024
KGS
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Average Price (USD/KGS)

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Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

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(USD/KGS)
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