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
| Molecular Formula | C6H14N2O2 |
| Molecular Weight | 146.1876 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | C5H9NO4S |
| Molecular Weight | 179.194 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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 |
|---|---|---|
| S-carboxymethylcysteine in the treatment of glue ear: quantitative systematic review. | 2001 |
|
| Effect of fudosteine, a cysteine derivative, on blood flow of tracheal microvasculature increased by airway inflammation. | 2001 Jul |
|
| Antioxidant activity of carbocysteine lysine salt monohydrate. | 2001 Sep |
|
| [Mucolytic agents for acute respiratory tract infections in infants: a pharmacoepidemiologic problem?]. | 2002 Nov |
|
| 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 |
|
| Phenylalanine 4-monooxygenase and the S-oxidation of S-carboxymethyl-L-cysteine. | 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 |
|
| 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 |
|
| 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 |
|
| Re(CO)(3) complexes synthesized via an improved preparation of aqueous fac-[Re(CO)(3)(H(2)O)(3)](+) as an aid in assessing (99m)Tc imaging agents. Structural characterization and solution behavior of complexes with thioether-bearing amino acids as tridentate ligands. | 2005 Jul 25 |
|
| Antioxidant therapies in COPD. | 2006 |
|
| The sulphoxidation of S-carboxymethyl-L-cysteine in COPD. | 2006 Apr |
|
| 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 |
|
| Phenylalanine 4-monooxygenase and the S-oxidation of S-carboxymethyl-L-cysteine by human cytosolic fractions. | 2008 |
|
| 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 |
|
| Variation in the attachment of Streptococcus pneumoniae to human pharyngeal epithelial cells after treatment with S-carboxymethylcysteine. | 2008 Aug |
|
| 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 |
|
| Measurement of phenylalanine monooxygenase (PAH) activities. | 2009 |
|
| Sequestration of Alkyltin(IV) compounds in aqueous solution: formation, stability, and empirical relationships for the binding of dimethyltin(IV) cation by N- and O-donor ligands. | 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 |
|
| Phenylalanine 4-monooxygenase and the role of endobiotic metabolism enzymes in xenobiotic biotransformation. | 2009 Oct |
|
| 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 |
|
| 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 |
|
| 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
| Substance Class |
Chemical
Created
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1D1Y95PXXA
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PARENT -> SALT/SOLVATE | |||
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PARENT -> SALT/SOLVATE | |||
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SOLVATE->ANHYDROUS |
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ACTIVE MOIETY |