U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C5H9NO4S
Molecular Weight 179.1956
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CARBOCYSTEINE

SMILES

C([C@@]([H])(C(=O)O)N)SCC(=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

HIDE SMILES / InChI

Description
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

Curator's Comment:: Carbocysteine is CNS active in animals. No human data available,

Approval Year

PubMed

PubMed

TitleDatePubMed
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
Direct determination of s-carboxymethyl-l-cysteine in syrups by reversed-phase high-performance liquid chromatography.
2001 Apr
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
Antioxidant activity of carbocysteine lysine salt monohydrate.
2001 Sep
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
[Mucolytic agents for acute respiratory tract infections in infants: a pharmacoepidemiologic problem?].
2002 Nov
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
S-carboxymethylcysteine inhibits the attachment of Streptococcus pneumoniae to human pharyngeal epithelial cells.
2003 Jun
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
Lack of congruence between cysteine dioxygenase activity and S-carboxymethyl-L-cysteine S-oxidation activity in rat cytosol.
2004 Aug
Reduced airway inflammation and remodeling in parallel with mucin 5AC protein expression decreased by s-carboxymethylcysteine, a mucoregulant, in the airways of rats exposed to sulfur dioxide.
2004 Aug
Phenylalanine hydroxylase: possible involvement in the S-oxidation of S-carboxymethyl-l-cysteine.
2004 Dec 1
Chemical modification of muscle protein in diabetes.
2004 May 15
Cancer-related anorexia/cachexia syndrome and oxidative stress: an innovative approach beyond current treatment.
2004 Oct
N-acetylcysteine inhibits Na+ absorption across human nasal epithelial cells.
2004 Oct
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
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
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
Protein and low molecular mass thiols as targets and inhibitors of glycation reactions.
2006 Dec
Antioxidant therapeutic targets in COPD.
2006 Jun
Cerebral formation in situ of S-carboxymethylcysteine after ifosfamide administration to mice: a further clue to the mechanism of ifosfamide encephalopathy.
2006 Mar 1
Efficacy of S-carboxymethyl-L-cysteine for otitis media with effusion.
2006 May
The suppression of enhanced bitterness intensity of macrolide dry syrup mixed with an acidic powder.
2007 Oct
Mechanisms for the proton mobility-dependent gas-phase fragmentation reactions of S-alkyl cysteine sulfoxide-containing peptide ions.
2007 Sep
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
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
Influence of various combinations of mucolytic agent and non-ionic surfactant on intestinal absorption of poorly absorbed hydrophilic compounds.
2008 Feb 12
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
Mouse recombinant phenylalanine monooxygenase and the S-oxygenation of thioether substrates.
2009 Mar-Apr
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
Isoprostanes-biomarkers of lipid peroxidation: their utility in evaluating oxidative stress and analysis.
2010 Nov 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 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
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
Name Type Language
CARBOCYSTEINE
INCI   MI   USAN  
USAN   INCI  
Official Name English
MUCOLASE
Brand Name English
3-((CARBOXYMETHYL)THIO)ALANINE
Systematic Name English
CARBOCISTEINE
EP   INN   MART.  
INN  
Official Name English
PECTOX
Brand Name English
CARBOCISTEIN
Common Name English
CARBOCIT
Brand Name English
NSC-14156
Code English
CARBOCYSTEINE [INCI]
Common Name English
LISOMUCIL
Brand Name English
LOVISCOL
Brand Name English
CARBOCISTEINE [INN]
Common Name English
AHR-3053
Code English
L-CARBOCISTEINE [JAN]
Common Name English
MUCICLAR
Brand Name English
L-CARBOCYSTEINE
WHO-DD  
Common Name English
REOMUCIL
Brand Name English
PULMOCLASE
Brand Name English
METHISTA
Brand Name English
CARBOCISTEINE [JAN]
Common Name English
LJ-206
Code English
R05CB03
Code English
S-(CARBOXYMETHYL)-L-CYSTEINE
Systematic Name English
MUCOFAN
Brand Name English
SIROXYL
Brand Name English
CARBOCYSTEINE [MI]
Common Name English
CARBOCISTEINE [EP MONOGRAPH]
Common Name English
L-CARBOCISTEINE
JAN  
Common Name English
MUCOLEX
Brand Name English
RHINATHIOL
Brand Name English
MUCOPRONT
Brand Name English
3-((CARBOXYMETHYL)THIO)-L-ALANINE
Systematic Name English
CARBOCYSTEINE [USAN]
Common Name English
CARBOCISTEINE [MART.]
Common Name English
TRANSBRONCHIN
Brand Name English
(2R)-2-AMINO-3-((CARBOXYMETHYL)THIO)PROPIONIC ACID
Systematic Name English
L-CARBOCISTEINE [WHO-DD]
Common Name English
MUCOCIS
Brand Name English
MUCODYNE
Brand Name English
CYSTEINE, S-(CARBOXYMETHYL)-
Systematic Name English
LJ 206
Code English
Classification Tree Code System Code
WHO-VATC QR05CB03
Created by admin on Fri Jun 25 21:18:59 UTC 2021 , Edited by admin on Fri Jun 25 21:18:59 UTC 2021
NCI_THESAURUS C74536
Created by admin on Fri Jun 25 21:18:59 UTC 2021 , Edited by admin on Fri Jun 25 21:18:59 UTC 2021
WHO-ATC R05CB03
Created by admin on Fri Jun 25 21:18:59 UTC 2021 , Edited by admin on Fri Jun 25 21:18:59 UTC 2021
Code System Code Type Description
ECHA (EC/EINECS)
211-327-5
Created by admin on Fri Jun 25 21:18:59 UTC 2021 , Edited by admin on Fri Jun 25 21:18:59 UTC 2021
PRIMARY
RXCUI
2023
Created by admin on Fri Jun 25 21:18:59 UTC 2021 , Edited by admin on Fri Jun 25 21:18:59 UTC 2021
PRIMARY RxNorm
ChEMBL
CHEMBL396416
Created by admin on Fri Jun 25 21:18:59 UTC 2021 , Edited by admin on Fri Jun 25 21:18:59 UTC 2021
PRIMARY
CAS
638-23-3
Created by admin on Fri Jun 25 21:18:59 UTC 2021 , Edited by admin on Fri Jun 25 21:18:59 UTC 2021
PRIMARY
EVMPD
SUB11790MIG
Created by admin on Fri Jun 25 21:18:59 UTC 2021 , Edited by admin on Fri Jun 25 21:18:59 UTC 2021
PRIMARY
INN
2884
Created by admin on Fri Jun 25 21:18:59 UTC 2021 , Edited by admin on Fri Jun 25 21:18:59 UTC 2021
PRIMARY
EVMPD
SUB21966
Created by admin on Fri Jun 25 21:18:59 UTC 2021 , Edited by admin on Fri Jun 25 21:18:59 UTC 2021
PRIMARY
DRUG CENTRAL
4160
Created by admin on Fri Jun 25 21:18:59 UTC 2021 , Edited by admin on Fri Jun 25 21:18:59 UTC 2021
PRIMARY
MESH
D002233
Created by admin on Fri Jun 25 21:18:59 UTC 2021 , Edited by admin on Fri Jun 25 21:18:59 UTC 2021
PRIMARY
NCI_THESAURUS
C83591
Created by admin on Fri Jun 25 21:18:59 UTC 2021 , Edited by admin on Fri Jun 25 21:18:59 UTC 2021
PRIMARY
EPA CompTox
638-23-3
Created by admin on Fri Jun 25 21:18:59 UTC 2021 , Edited by admin on Fri Jun 25 21:18:59 UTC 2021
PRIMARY
DRUG BANK
DB04339
Created by admin on Fri Jun 25 21:18:59 UTC 2021 , Edited by admin on Fri Jun 25 21:18:59 UTC 2021
PRIMARY
MERCK INDEX
M3072
Created by admin on Fri Jun 25 21:18:59 UTC 2021 , Edited by admin on Fri Jun 25 21:18:59 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
CARBOCISTEINE
Created by admin on Fri Jun 25 21:18:59 UTC 2021 , Edited by admin on Fri Jun 25 21:18:59 UTC 2021
PRIMARY
PUBCHEM
193653
Created by admin on Fri Jun 25 21:18:59 UTC 2021 , Edited by admin on Fri Jun 25 21:18:59 UTC 2021
PRIMARY
FDA UNII
740J2QX53R
Created by admin on Fri Jun 25 21:18:59 UTC 2021 , Edited by admin on Fri Jun 25 21:18:59 UTC 2021
PRIMARY