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 |
|---|---|---|
| Study about the inhibition of L-cysteine derivatives of nucleic acid bases in protein production. | 2001 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| Phenylalanine hydroxylase: possible involvement in the S-oxidation of S-carboxymethyl-l-cysteine. | 2004 Dec 1 |
|
| Cancer-related anorexia/cachexia syndrome and oxidative stress: an innovative approach beyond current treatment. | 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 |
|
| 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 |
|
| The sulphoxidation of S-carboxymethyl-L-cysteine in COPD. | 2006 Apr |
|
| Protein and low molecular mass thiols as targets and inhibitors of glycation reactions. | 2006 Dec |
|
| Thiodiglycolic acid and dermatological reactions following S-carboxymethyl-L-cysteine administration. | 2006 Feb |
|
| Cerebral formation in situ of S-carboxymethylcysteine after ifosfamide administration to mice: a further clue to the mechanism of ifosfamide encephalopathy. | 2006 Mar 1 |
|
| Evidence for inactivation of cysteine proteases by reactive carbonyls via glycation of active site thiols. | 2006 Sep 1 |
|
| Bacterial lysate in the prevention of acute exacerbation of COPD and in respiratory recurrent infections. | 2007 |
|
| The suppression of enhanced bitterness intensity of macrolide dry syrup mixed with an acidic powder. | 2007 Oct |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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
| Substance Class |
Chemical
Created
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1D1Y95PXXA
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PARENT -> SALT/SOLVATE | |||
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SOLVATE->ANHYDROUS |
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ACTIVE MOIETY |