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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
Reduction and s-carboxymethylation of proteins: large-scale method.
2007 Feb 1
Measurement of phenylalanine monooxygenase (PAH) activities.
2009
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