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 |
|---|---|---|
| Study about the inhibition of L-cysteine derivatives of nucleic acid bases in protein production. | 2001 |
|
| S-carboxymethylcysteine in the treatment of glue ear: quantitative systematic review. | 2001 |
|
| Study on the inhibition of protein production by L-cysteine derivatives of nucleic acid bases. | 2002 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| Thiodiglycolic acid and dermatological reactions following S-carboxymethyl-L-cysteine administration. | 2006 Feb |
|
| 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 |
|
| Cerebral formation in situ of S-carboxymethylcysteine after ifosfamide administration to mice: a further clue to the mechanism of ifosfamide encephalopathy. | 2006 Mar 1 |
|
| Bacterial lysate in the prevention of acute exacerbation of COPD and in respiratory recurrent infections. | 2007 |
|
| Influence of various combinations of mucolytic agent and non-ionic surfactant on intestinal absorption of poorly absorbed hydrophilic compounds. | 2008 Feb 12 |
|
| 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 |
|
| Phenylalanine 4-monooxygenase and the role of endobiotic metabolism enzymes in xenobiotic biotransformation. | 2009 Oct |
|
| The pharmacokinetics of orally administered S-carboxymethyl-L-cysteine in the dog, calf and sheep. | 2010 Feb 19 |
|
| 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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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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