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 |
|---|---|---|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| Induction of cysteine dioxygenase activity by oral administration of cysteine analogues to the rat: implications for drug efficacy and safety. | 2005 |
|
| Phenylalanine 4-monooxygenase and the S-oxidation of S-carboxymethyl-L-cysteine in HepG2 cells. | 2005 |
|
| Analysis of plasma amino acids by HPLC with photodiode array and fluorescence detection. | 2005 Apr |
|
| 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 |
|
| Protein and low molecular mass thiols as targets and inhibitors of glycation reactions. | 2006 Dec |
|
| S-CMC-Lys-dependent stimulation of electrogenic glutathione secretion by human respiratory epithelium. | 2006 Jan |
|
| 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 |
|
| Bacterial lysate in the prevention of acute exacerbation of COPD and in respiratory recurrent infections. | 2007 |
|
| Phenylalanine 4-monooxygenase and the S-oxidation of S-carboxymethyl-L-cysteine by human cytosolic fractions. | 2008 |
|
| 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 |
|
| Glutaraldehyde is an effective cross-linker for production of antibodies against advanced glycation end-products. | 2008 May 20 |
|
| The effect and mechanism of action of carbocysteine on airway bacterial load in rats chronically exposed to cigarette smoke. | 2010 Oct |
|
| Comparative metabolism of cyclophosphamide and ifosfamide in the mouse using UPLC-ESI-QTOFMS-based metabolomics. | 2010 Oct 1 |
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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1D1Y95PXXA
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SUB127326
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3892
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ACTIVE MOIETY
PARENT (SALT/SOLVATE)
SUBSTANCE RECORD
