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
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/20956181Curator'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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20956181
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.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16229978
Curator's Comment: Carbocysteine is CNS active in animals. No human data available,
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Conditions
Condition | Modality | Targets | Highest Phase | Product |
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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 |
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S-carboxymethylcysteine in the treatment of glue ear: quantitative systematic review. | 2001 |
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Direct determination of s-carboxymethyl-l-cysteine in syrups by reversed-phase high-performance liquid chromatography. | 2001 Apr |
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Modulating effects of mucoregulating drugs on the attachment of Haemophilus influenzae. | 2001 Mar |
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S-carboxymethylcysteine inhibits neutrophil activation mediated by N-formyl-methionyl-leucyl-phenylalanine. | 2002 Aug 2 |
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Prolonged survival after experimental paraquat intoxication: role of alternative antioxidants. | 2002 Feb |
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[Mucolytic agents for acute respiratory tract infections in infants: a pharmacoepidemiologic problem?]. | 2002 Nov |
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Thirty-five cases of S-carboxymethylcysteine use in paraquat poisoning. | 2003 Feb |
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Carbocysteine lysine salt monohydrate (SCMC-LYS) is a selective scavenger of reactive oxygen intermediates (ROIs). | 2003 Jan-Mar |
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S-carboxymethylcysteine inhibits the attachment of Streptococcus pneumoniae to human pharyngeal epithelial cells. | 2003 Jun |
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Effect of glucose concentration on formation of AGEs in erythrocytes in vitro. | 2005 Jun |
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Antioxidant therapies in COPD. | 2006 |
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Thiodiglycolic acid and dermatological reactions following S-carboxymethyl-L-cysteine administration. | 2006 Feb |
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Cerebral formation in situ of S-carboxymethylcysteine after ifosfamide administration to mice: a further clue to the mechanism of ifosfamide encephalopathy. | 2006 Mar 1 |
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S-CMC-Lys protective effects on human respiratory cells during oxidative stress. | 2008 |
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Usefulness of antibodies for evaluating the biological significance of AGEs. | 2008 Apr |
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Glutaraldehyde is an effective cross-linker for production of antibodies against advanced glycation end-products. | 2008 May 20 |
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Phenylalanine 4-monooxygenase and the role of endobiotic metabolism enzymes in xenobiotic biotransformation. | 2009 Oct |
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Association between lung function and exacerbation frequency in patients with COPD. | 2010 Dec 9 |
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Isoprostanes-biomarkers of lipid peroxidation: their utility in evaluating oxidative stress and analysis. | 2010 Nov 17 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.medicines.org.uk/emc/medicine/27807
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16510461
Carbocysteine inhibited rhinovirus (RV)2 and RV14 infection in human tracheal epithelial cells in a concentration-dependent manner, the maximum effect being obtained at 10 and 30 μM
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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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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
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