Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C5H9NO4S |
| Molecular Weight | 179.194 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
N[C@@H](CSCC(O)=O)C(O)=O
InChI
InChIKey=GBFLZEXEOZUWRN-VKHMYHEASA-N
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
DescriptionCurator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/19239402 | https://www.ncbi.nlm.nih.gov/pubmed/19281081
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/19239402 | https://www.ncbi.nlm.nih.gov/pubmed/19281081
S-Carboxymethylcysteine (carbocysteine or SCMC; also available in the lysinate form, SCMC-Lys) is a mucoactive drug, has antioxidant and anti-inflammatory properties. Carbocysteine has been recently recognized as an effective and safe treatment for the long-term management of COPD, able to reduce the incidence of exacerbations and improve patient quality of life. Moreover, carbocysteine was effective in counteracting some symptoms associated with cancer cachexia. Preclinical and clinical studies have demonstrated that the antioxidant and anti-inflammatory properties of carbocysteine are more important than mucolysis itself for its therapeutic efficacy. Therefore, carbocysteine may be able to reverse the oxidative stress associated with several chronic inflammatory diseases, such as cardiovascular diseases and neurodegenerative disorders.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Carbocisteine Approved UseCarbocisteine is a mucolytic agent for the adjunctive therapy of respiratory tract disorders characterised by excessive, viscous mucus, including chronic obstructive airways disease. |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Direct determination of s-carboxymethyl-l-cysteine in syrups by reversed-phase high-performance liquid chromatography. | 2001 Apr |
|
| Effect of fudosteine, a cysteine derivative, on blood flow of tracheal microvasculature increased by airway inflammation. | 2001 Jul |
|
| Lack of congruence between cysteine dioxygenase activity and S-carboxymethyl-L-cysteine S-oxidation activity in rat cytosol. | 2004 Aug |
|
| Analysis of plasma amino acids by HPLC with photodiode array and fluorescence detection. | 2005 Apr |
|
| The sulphoxidation of S-carboxymethyl-L-cysteine in COPD. | 2006 Apr |
|
| S-CMC-Lys-dependent stimulation of electrogenic glutathione secretion by human respiratory epithelium. | 2006 Jan |
|
| Synergistic effect of interleukin 1 alpha on nontypeable Haemophilus influenzae-induced up-regulation of human beta-defensin 2 in middle ear epithelial cells. | 2006 Jan 24 |
|
| Efficacy of S-carboxymethyl-L-cysteine for otitis media with effusion. | 2006 May |
|
| Bacterial lysate in the prevention of acute exacerbation of COPD and in respiratory recurrent infections. | 2007 |
|
| The suppression of enhanced bitterness intensity of macrolide dry syrup mixed with an acidic powder. | 2007 Oct |
|
| Mechanisms for the proton mobility-dependent gas-phase fragmentation reactions of S-alkyl cysteine sulfoxide-containing peptide ions. | 2007 Sep |
|
| Influence of various combinations of mucolytic agent and non-ionic surfactant on intestinal absorption of poorly absorbed hydrophilic compounds. | 2008 Feb 12 |
|
| Immunochemical detection of Nepsilon-(carboxyethyl)lysine using a specific antibody. | 2008 Mar 20 |
|
| s-Carboxymethylcysteine inhibits carbachol-induced constriction of epithelium-denuded rat and human airway preparations. | 2008 May |
|
| Human phenylalanine monooxygenase and thioether metabolism. | 2009 Jan |
|
| The activity of wild type and mutant phenylalanine hydroxylase with respect to the C-oxidation of phenylalanine and the S-oxidation of S-carboxymethyl-L-cysteine. | 2009 Jan |
|
| Modulation of the cellular expression of circulating advanced glycation end-product receptors in type 2 diabetic nephropathy. | 2010 |
Patents
Sample Use Guides
Dosage is based upon an initial daily dosage of 2250 mg carbocysteine (6 capsules) in divided doses, reducing to 1500 mg (4 capsules) daily in divided doses when a satisfactory response is obtained. For example, two capsules three times a day reducing to one capsule four times a day.
Route of Administration:
Oral
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WHO-VATC |
QR05CB03
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NCI_THESAURUS |
C74536
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WHO-ATC |
R05CB03
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2023
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CHEMBL396416
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638-23-3
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SUB11790MIG
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100000092161
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740J2QX53R
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2884
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SUB21966
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D002233
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16163
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C83591
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DTXSID30110060
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DB04339
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m3072
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CARBOCISTEINE
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14156
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193653
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740J2QX53R
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
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