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
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 |
|---|---|---|
| Direct determination of s-carboxymethyl-l-cysteine in syrups by reversed-phase high-performance liquid chromatography. | 2001 Apr |
|
| Study on the inhibition of protein production by L-cysteine derivatives of nucleic acid bases. | 2002 |
|
| 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 |
|
| 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 |
|
| Lack of congruence between cysteine dioxygenase activity and S-carboxymethyl-L-cysteine S-oxidation activity in rat cytosol. | 2004 Aug |
|
| Chemical modification of muscle protein in diabetes. | 2004 May 15 |
|
| 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 |
|
| 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 |
|
| Effect of glucose concentration on formation of AGEs in erythrocytes in vitro. | 2005 Jun |
|
| 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 |
|
| S-CMC-Lys-dependent stimulation of electrogenic glutathione secretion by human respiratory epithelium. | 2006 Jan |
|
| Synergistic effect of interleukin 1 alpha on nontypeable Haemophilus influenzae-induced up-regulation of human beta-defensin 2 in middle ear epithelial cells. | 2006 Jan 24 |
|
| Efficacy of S-carboxymethyl-L-cysteine for otitis media with effusion. | 2006 May |
|
| Variation in the attachment of Streptococcus pneumoniae to human pharyngeal epithelial cells after treatment with S-carboxymethylcysteine. | 2008 Aug |
|
| 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 |
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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100000092161
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740J2QX53R
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2884
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SUB21966
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4160
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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
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
