Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C6H14N2O2.C5H9NO4S.H2O |
| Molecular Weight | 343.397 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.NCCCC[C@H](N)C(O)=O.N[C@@H](CSCC(O)=O)C(O)=O
InChI
InChIKey=QVJUWKMADMJHJZ-PBUQCQDLSA-N
InChI=1S/C6H14N2O2.C5H9NO4S.H2O/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);1H2/t5-;3-;/m00./s1
| 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 |
| Molecular Formula | H2O |
| Molecular Weight | 18.0153 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| 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 |
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. |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
13.38 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7139067/ |
1.5 g single, oral dose: 1.5 g route of administration: Oral experiment type: SINGLE co-administered: |
CARBOCYSTEINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
8.02 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16724543/ |
750 mg single, oral dose: 750 mg route of administration: Oral experiment type: SINGLE co-administered: |
CARBOCYSTEINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
5.6 μg/mL |
1000 mg single, oral dose: 1000 mg route of administration: Oral experiment type: SINGLE co-administered: |
CARBOCYSTEINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
63.15 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7139067/ |
1.5 g single, oral dose: 1.5 g route of administration: Oral experiment type: SINGLE co-administered: |
CARBOCYSTEINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
14.88 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16724543/ |
750 mg single, oral dose: 750 mg route of administration: Oral experiment type: SINGLE co-administered: |
CARBOCYSTEINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
22.8 μg × h/mL |
1000 mg single, oral dose: 1000 mg route of administration: Oral experiment type: SINGLE co-administered: |
CARBOCYSTEINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2.05 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7139067/ |
1.5 g single, oral dose: 1.5 g route of administration: Oral experiment type: SINGLE co-administered: |
CARBOCYSTEINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
2.02 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16724543/ |
750 mg single, oral dose: 750 mg route of administration: Oral experiment type: SINGLE co-administered: |
CARBOCYSTEINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
1.5 h |
1000 mg single, oral dose: 1000 mg route of administration: Oral experiment type: SINGLE co-administered: |
CARBOCYSTEINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
| Dose | Population | Adverse events |
|---|---|---|
3 g 1 times / day multiple, oral Highest studied dose Dose: 3 g, 1 times / day Route: oral Route: multiple Dose: 3 g, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
|
2.7 g 1 times / day multiple, oral Studied dose Dose: 2.7 g, 1 times / day Route: oral Route: multiple Dose: 2.7 g, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Association between lung function and exacerbation frequency in patients with COPD. | 2010-12-09 |
|
| Isoprostanes-biomarkers of lipid peroxidation: their utility in evaluating oxidative stress and analysis. | 2010-11-17 |
|
| 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. | 2010-10-15 |
|
| Comparative metabolism of cyclophosphamide and ifosfamide in the mouse using UPLC-ESI-QTOFMS-based metabolomics. | 2010-10-01 |
|
| The effect and mechanism of action of carbocysteine on airway bacterial load in rats chronically exposed to cigarette smoke. | 2010-10 |
|
| The pharmacokinetics of orally administered S-carboxymethyl-L-cysteine in the dog, calf and sheep. | 2010-02-19 |
|
| Modulation of the cellular expression of circulating advanced glycation end-product receptors in type 2 diabetic nephropathy. | 2010 |
|
| Phenylalanine 4-monooxygenase and the role of endobiotic metabolism enzymes in xenobiotic biotransformation. | 2009-10 |
|
| Mouse recombinant phenylalanine monooxygenase and the S-oxygenation of thioether substrates. | 2009-04-16 |
|
| Human phenylalanine monooxygenase and thioether metabolism. | 2009-01 |
|
| 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. | 2009-01 |
|
| 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 |
|
| Variation in the attachment of Streptococcus pneumoniae to human pharyngeal epithelial cells after treatment with S-carboxymethylcysteine. | 2008-08 |
|
| Glutaraldehyde is an effective cross-linker for production of antibodies against advanced glycation end-products. | 2008-05-20 |
|
| s-Carboxymethylcysteine inhibits carbachol-induced constriction of epithelium-denuded rat and human airway preparations. | 2008-05 |
|
| Usefulness of antibodies for evaluating the biological significance of AGEs. | 2008-04 |
|
| Immunological detection of N omega-(Carboxymethyl)arginine by a specific antibody. | 2008-04 |
|
| Immunochemical detection of Nepsilon-(carboxyethyl)lysine using a specific antibody. | 2008-03-20 |
|
| Influence of various combinations of mucolytic agent and non-ionic surfactant on intestinal absorption of poorly absorbed hydrophilic compounds. | 2008-02-12 |
|
| 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 |
|
| The suppression of enhanced bitterness intensity of macrolide dry syrup mixed with an acidic powder. | 2007-10 |
|
| Mechanisms for the proton mobility-dependent gas-phase fragmentation reactions of S-alkyl cysteine sulfoxide-containing peptide ions. | 2007-09 |
|
| Reduction and s-carboxymethylation of proteins: large-scale method. | 2007-02-01 |
|
| Bacterial lysate in the prevention of acute exacerbation of COPD and in respiratory recurrent infections. | 2007 |
|
| Protein and low molecular mass thiols as targets and inhibitors of glycation reactions. | 2006-12 |
|
| Evidence for inactivation of cysteine proteases by reactive carbonyls via glycation of active site thiols. | 2006-09-01 |
|
| Antioxidant therapeutic targets in COPD. | 2006-06 |
|
| Efficacy of S-carboxymethyl-L-cysteine for otitis media with effusion. | 2006-05 |
|
| The sulphoxidation of S-carboxymethyl-L-cysteine in COPD. | 2006-04 |
|
| Cerebral formation in situ of S-carboxymethylcysteine after ifosfamide administration to mice: a further clue to the mechanism of ifosfamide encephalopathy. | 2006-03-01 |
|
| Thiodiglycolic acid and dermatological reactions following S-carboxymethyl-L-cysteine administration. | 2006-02 |
|
| Synergistic effect of interleukin 1 alpha on nontypeable Haemophilus influenzae-induced up-regulation of human beta-defensin 2 in middle ear epithelial cells. | 2006-01-24 |
|
| S-CMC-Lys-dependent stimulation of electrogenic glutathione secretion by human respiratory epithelium. | 2006-01 |
|
| Antioxidant therapies in COPD. | 2006 |
|
| S-carboxymethylcysteine normalises airway responsiveness in sensitised and challenged mice. | 2005-10 |
|
| 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. | 2005-08 |
|
| 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. | 2005-07-25 |
|
| 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. | 2005-07 |
|
| Effect of glucose concentration on formation of AGEs in erythrocytes in vitro. | 2005-06 |
|
| Analysis of plasma amino acids by HPLC with photodiode array and fluorescence detection. | 2005-04 |
|
| 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 |
|
| Phenylalanine hydroxylase: possible involvement in the S-oxidation of S-carboxymethyl-l-cysteine. | 2004-12-01 |
|
| Exhaled Interleukine-6 and 8-isoprostane in chronic obstructive pulmonary disease: effect of carbocysteine lysine salt monohydrate (SCMC-Lys). | 2004-11-28 |
|
| Cancer-related anorexia/cachexia syndrome and oxidative stress: an innovative approach beyond current treatment. | 2004-10 |
|
| Phenylalanine 4-monooxygenase and the S-oxidation of S-carboxymethyl-L-cysteine. | 2004 |
|
| Effect of fudosteine, a cysteine derivative, on blood flow of tracheal microvasculature increased by airway inflammation. | 2001-07 |
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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Edited
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| Record UNII |
QA5ZP9OL3E
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| Record Status |
Validated (UNII)
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| Record Version |
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ANHYDROUS->SOLVATE |
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PARENT -> SALT/SOLVATE |
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |
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