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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
Structure of CARBOCYSTEINE

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

HIDE SMILES / InChI

Description

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

Approval Year

PubMed

PubMed

TitleDatePubMed
Effect of fudosteine, a cysteine derivative, on blood flow of tracheal microvasculature increased by airway inflammation.
2001 Jul
Phenylalanine 4-monooxygenase and the S-oxidation of S-carboxymethyl-L-cysteine.
2004
Phenylalanine hydroxylase: possible involvement in the S-oxidation of S-carboxymethyl-l-cysteine.
2004 Dec 1
Exhaled Interleukine-6 and 8-isoprostane in chronic obstructive pulmonary disease: effect of carbocysteine lysine salt monohydrate (SCMC-Lys).
2004 Nov 28
Cancer-related anorexia/cachexia syndrome and oxidative stress: an innovative approach beyond current treatment.
2004 Oct
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
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
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
S-carboxymethylcysteine normalises airway responsiveness in sensitised and challenged mice.
2005 Oct
Antioxidant therapies in COPD.
2006
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
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
Evidence for inactivation of cysteine proteases by reactive carbonyls via glycation of active site thiols.
2006 Sep 1
Bacterial lysate in the prevention of acute exacerbation of COPD and in respiratory recurrent infections.
2007
Reduction and s-carboxymethylation of proteins: large-scale method.
2007 Feb 1
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
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
Usefulness of antibodies for evaluating the biological significance of AGEs.
2008 Apr
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
Immunochemical detection of Nepsilon-(carboxyethyl)lysine using a specific antibody.
2008 Mar 20
s-Carboxymethylcysteine inhibits carbachol-induced constriction of epithelium-denuded rat and human airway preparations.
2008 May
Glutaraldehyde is an effective cross-linker for production of antibodies against advanced glycation end-products.
2008 May 20
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
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
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
Isoprostanes-biomarkers of lipid peroxidation: their utility in evaluating oxidative stress and analysis.
2010 Nov 17
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
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
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
CARBOCISTEINE [EP]
Common 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
L-CARBOCYSTEINE [WHO-DD]
Common 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
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
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 Tue Mar 06 11:57:01 UTC 2018 , Edited by admin on Tue Mar 06 11:57:01 UTC 2018
WHO-ATC R05CB03
Created by admin on Tue Mar 06 11:57:01 UTC 2018 , Edited by admin on Tue Mar 06 11:57:01 UTC 2018
Code System Code Type Description
ECHA (EC/EINECS)
211-327-5
Created by admin on Tue Mar 06 11:57:01 UTC 2018 , Edited by admin on Tue Mar 06 11:57:01 UTC 2018
PRIMARY
RXCUI
2023
Created by admin on Tue Mar 06 11:57:01 UTC 2018 , Edited by admin on Tue Mar 06 11:57:01 UTC 2018
PRIMARY RxNorm
ChEMBL
CHEMBL396416
Created by admin on Tue Mar 06 11:57:01 UTC 2018 , Edited by admin on Tue Mar 06 11:57:01 UTC 2018
PRIMARY
CAS
638-23-3
Created by admin on Tue Mar 06 11:57:01 UTC 2018 , Edited by admin on Tue Mar 06 11:57:01 UTC 2018
PRIMARY
EVMPD
SUB11790MIG
Created by admin on Tue Mar 06 11:57:01 UTC 2018 , Edited by admin on Tue Mar 06 11:57:01 UTC 2018
PRIMARY
INN
2884
Created by admin on Tue Mar 06 11:57:01 UTC 2018 , Edited by admin on Tue Mar 06 11:57:01 UTC 2018
PRIMARY
EVMPD
SUB21966
Created by admin on Tue Mar 06 11:57:01 UTC 2018 , Edited by admin on Tue Mar 06 11:57:01 UTC 2018
PRIMARY
MESH
D002233
Created by admin on Tue Mar 06 11:57:01 UTC 2018 , Edited by admin on Tue Mar 06 11:57:01 UTC 2018
PRIMARY
NCI_THESAURUS
C83591
Created by admin on Tue Mar 06 11:57:01 UTC 2018 , Edited by admin on Tue Mar 06 11:57:01 UTC 2018
PRIMARY
EPA CompTox
638-23-3
Created by admin on Tue Mar 06 11:57:01 UTC 2018 , Edited by admin on Tue Mar 06 11:57:01 UTC 2018
PRIMARY
DRUG BANK
DB04339
Created by admin on Tue Mar 06 11:57:01 UTC 2018 , Edited by admin on Tue Mar 06 11:57:01 UTC 2018
PRIMARY
MERCK INDEX
M3072
Created by admin on Tue Mar 06 11:57:01 UTC 2018 , Edited by admin on Tue Mar 06 11:57:01 UTC 2018
PRIMARY Merck Index
WIKIPEDIA
CARBOCISTEINE
Created by admin on Tue Mar 06 11:57:01 UTC 2018 , Edited by admin on Tue Mar 06 11:57:01 UTC 2018
PRIMARY
PUBCHEM
193653
Created by admin on Tue Mar 06 11:57:01 UTC 2018 , Edited by admin on Tue Mar 06 11:57:01 UTC 2018
PRIMARY SWITZERF