Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C5H9NO4S |
| Molecular Weight | 179.1956 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C([C@@]([H])(C(=O)O)N)SCC(=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 |
|---|---|---|
| Study about the inhibition of L-cysteine derivatives of nucleic acid bases in protein production. | 2001 |
|
| S-carboxymethylcysteine in the treatment of glue ear: quantitative systematic review. | 2001 |
|
| Direct determination of s-carboxymethyl-l-cysteine in syrups by reversed-phase high-performance liquid chromatography. | 2001 Apr |
|
| Insights into the mechanisms of ifosfamide encephalopathy: drug metabolites have agonistic effects on alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA)/kainate receptors and induce cellular acidification in mouse cortical neurons. | 2001 Dec |
|
| Modulating effects of mucoregulating drugs on the attachment of Haemophilus influenzae. | 2001 Mar |
|
| Antioxidant activity of carbocysteine lysine salt monohydrate. | 2001 Sep |
|
| Study on the inhibition of protein production by L-cysteine derivatives of nucleic acid bases. | 2002 |
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| S-carboxymethylcysteine inhibits neutrophil activation mediated by N-formyl-methionyl-leucyl-phenylalanine. | 2002 Aug 2 |
|
| Prolonged survival after experimental paraquat intoxication: role of alternative antioxidants. | 2002 Feb |
|
| [Mucolytic agents for acute respiratory tract infections in infants: a pharmacoepidemiologic problem?]. | 2002 Nov |
|
| An investigation into the inter-relationships of sulphur xeno-biotransformation pathways in Parkinson's and motor neurone diseases. | 2003 |
|
| 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 |
|
| Subcutaneous interleukin-2 in combination with medroxyprogesterone acetate and antioxidants in advanced cancer responders to previous chemotherapy: phase II study evaluating clinical, quality of life, and laboratory parameters. | 2003 Jul-Aug |
|
| S-carboxymethylcysteine inhibits the attachment of Streptococcus pneumoniae to human pharyngeal epithelial cells. | 2003 Jun |
|
| Phenylalanine 4-monooxygenase and the S-oxidation of S-carboxymethyl-L-cysteine. | 2004 |
|
| The effect of cysteine analogues on the excretion of urinary sulphate in the rat following cysteine administration. | 2004 |
|
| Lack of congruence between cysteine dioxygenase activity and S-carboxymethyl-L-cysteine S-oxidation activity in rat cytosol. | 2004 Aug |
|
| Reduced airway inflammation and remodeling in parallel with mucin 5AC protein expression decreased by s-carboxymethylcysteine, a mucoregulant, in the airways of rats exposed to sulfur dioxide. | 2004 Aug |
|
| Phenylalanine hydroxylase: possible involvement in the S-oxidation of S-carboxymethyl-l-cysteine. | 2004 Dec 1 |
|
| Chemical modification of muscle protein in diabetes. | 2004 May 15 |
|
| 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 |
|
| Thiodiglycolic acid as a possible causative agent of fixed drug eruption provoked only after continuous administration of S-carboxymethyl-L-cysteine: case report and review of reported cases. | 2005 Jul |
|
| Effect of glucose concentration on formation of AGEs in erythrocytes in vitro. | 2005 Jun |
|
| S-carboxymethylcysteine normalises airway responsiveness in sensitised and challenged mice. | 2005 Oct |
|
| Antioxidant therapies in COPD. | 2006 |
|
| Protein and low molecular mass thiols as targets and inhibitors of glycation reactions. | 2006 Dec |
|
| Antioxidant therapeutic targets in COPD. | 2006 Jun |
|
| Cerebral formation in situ of S-carboxymethylcysteine after ifosfamide administration to mice: a further clue to the mechanism of ifosfamide encephalopathy. | 2006 Mar 1 |
|
| Efficacy of S-carboxymethyl-L-cysteine for otitis media with effusion. | 2006 May |
|
| 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 |
|
| Immunological detection of N omega-(Carboxymethyl)arginine by a specific antibody. | 2008 Apr |
|
| Variation in the attachment of Streptococcus pneumoniae to human pharyngeal epithelial cells after treatment with S-carboxymethylcysteine. | 2008 Aug |
|
| Influence of various combinations of mucolytic agent and non-ionic surfactant on intestinal absorption of poorly absorbed hydrophilic compounds. | 2008 Feb 12 |
|
| Measurement of phenylalanine monooxygenase (PAH) activities. | 2009 |
|
| 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 |
|
| Mouse recombinant phenylalanine monooxygenase and the S-oxygenation of thioether substrates. | 2009 Mar-Apr |
|
| Modulation of the cellular expression of circulating advanced glycation end-product receptors in type 2 diabetic nephropathy. | 2010 |
|
| Association between lung function and exacerbation frequency in patients with COPD. | 2010 Dec 9 |
|
| The pharmacokinetics of orally administered S-carboxymethyl-L-cysteine in the dog, calf and sheep. | 2010 Feb 19 |
|
| Isoprostanes-biomarkers of lipid peroxidation: their utility in evaluating oxidative stress and analysis. | 2010 Nov 17 |
|
| Inactivation by Hg2+ and methylmercury of the glutamine/amino acid transporter (ASCT2) reconstituted in liposomes: Prediction of the involvement of a CXXC motif by homology modelling. | 2010 Oct 15 |
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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211-327-5
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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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2884
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SUB21966
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4160
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D002233
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C83591
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638-23-3
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DB04339
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M3072
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CARBOCISTEINE
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193653
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740J2QX53R
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
