Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C6H14N2O2.C5H9NO4S |
| Molecular Weight | 325.382 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NCCCC[C@H](N)C(O)=O.N[C@@H](CSCC(O)=O)C(O)=O
InChI
InChIKey=SAGXGPWVLUSDSQ-RVZXSAGBSA-N
InChI=1S/C6H14N2O2.C5H9NO4S/c7-4-2-1-3-5(8)6(9)10;6-3(5(9)10)1-11-2-4(7)8/h5H,1-4,7-8H2,(H,9,10);3H,1-2,6H2,(H,7,8)(H,9,10)/t5-;3-/m00/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 |
|---|---|---|
| Study about the inhibition of L-cysteine derivatives of nucleic acid bases in protein production. | 2001 |
|
| Effect of fudosteine, a cysteine derivative, on blood flow of tracheal microvasculature increased by airway inflammation. | 2001 Jul |
|
| [Mucolytic agents for acute respiratory tract infections in infants: a pharmacoepidemiologic problem?]. | 2002 Nov |
|
| Thirty-five cases of S-carboxymethylcysteine use in paraquat poisoning. | 2003 Feb |
|
| Carbocysteine lysine salt monohydrate (SCMC-LYS) is a selective scavenger of reactive oxygen intermediates (ROIs). | 2003 Jan-Mar |
|
| S-carboxymethylcysteine inhibits the attachment of Streptococcus pneumoniae to human pharyngeal epithelial cells. | 2003 Jun |
|
| The effect of cysteine analogues on the excretion of urinary sulphate in the rat following cysteine administration. | 2004 |
|
| Phenylalanine hydroxylase: possible involvement in the S-oxidation of S-carboxymethyl-l-cysteine. | 2004 Dec 1 |
|
| Exhaled Interleukine-6 and 8-isoprostane in chronic obstructive pulmonary disease: effect of carbocysteine lysine salt monohydrate (SCMC-Lys). | 2004 Nov 28 |
|
| Cancer-related anorexia/cachexia syndrome and oxidative stress: an innovative approach beyond current treatment. | 2004 Oct |
|
| N-acetylcysteine inhibits Na+ absorption across human nasal epithelial cells. | 2004 Oct |
|
| Phenylalanine 4-monooxygenase and the S-oxidation of S-carboxymethyl-L-cysteine in HepG2 cells. | 2005 |
|
| Evidence for the formation of adducts and S-(carboxymethyl)cysteine on reaction of alpha-dicarbonyl compounds with thiol groups on amino acids, peptides, and proteins. | 2005 Aug |
|
| S-carboxymethylcysteine normalises airway responsiveness in sensitised and challenged mice. | 2005 Oct |
|
| Antioxidant therapies in COPD. | 2006 |
|
| 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 |
|
| Bacterial lysate in the prevention of acute exacerbation of COPD and in respiratory recurrent infections. | 2007 |
|
| Reduction and s-carboxymethylation of proteins: large-scale method. | 2007 Feb 1 |
|
| 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 |
|
| The role for S-carboxymethylcysteine (carbocisteine) in the management of chronic obstructive pulmonary disease. | 2008 |
|
| S-CMC-Lys protective effects on human respiratory cells during oxidative stress. | 2008 |
|
| Usefulness of antibodies for evaluating the biological significance of AGEs. | 2008 Apr |
|
| Immunological detection of N omega-(Carboxymethyl)arginine by a specific antibody. | 2008 Apr |
|
| 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 |
|
| Association between lung function and exacerbation frequency in patients with COPD. | 2010 Dec 9 |
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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SUB01046MIG
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1427149
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1D1Y95PXXA
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DTXSID60964336
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49673-81-6
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100000090119
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256-425-9
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SUB127326
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3892
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ACTIVE MOIETY
PARENT (SALT/SOLVATE)
SUBSTANCE RECORD
