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
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 |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/20956181Curator'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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20956181
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.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16229978
Curator's Comment: Carbocysteine is CNS active in animals. No human data available,
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 |
---|---|---|
S-carboxymethylcysteine in the treatment of glue ear: quantitative systematic review. | 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 |
|
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 |
|
Chemical modification of muscle protein in diabetes. | 2004 May 15 |
|
N-acetylcysteine inhibits Na+ absorption across human nasal epithelial cells. | 2004 Oct |
|
Analysis of plasma amino acids by HPLC with photodiode array and fluorescence detection. | 2005 Apr |
|
Antioxidant therapeutic targets in COPD. | 2006 Jun |
|
Phenylalanine 4-monooxygenase and the S-oxidation of S-carboxymethyl-L-cysteine by human cytosolic fractions. | 2008 |
|
S-CMC-Lys protective effects on human respiratory cells during oxidative stress. | 2008 |
|
Immunological detection of N omega-(Carboxymethyl)arginine by a specific antibody. | 2008 Apr |
|
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 |
|
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 |
|
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
In Vivo Use Guide
Sources: https://www.medicines.org.uk/emc/medicine/27807
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16510461
Carbocysteine inhibited rhinovirus (RV)2 and RV14 infection in human tracheal epithelial cells in a concentration-dependent manner, the maximum effect being obtained at 10 and 30 μM
Substance Class |
Chemical
Created
by
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on
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Record UNII |
740J2QX53R
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Validated (UNII)
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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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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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m3072
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CARBOCISTEINE
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14156
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193653
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