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

Details

Stereochemistry ABSOLUTE
Molecular Formula C5H9NO4S
Molecular Weight 179.194
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
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
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
Modulating effects of mucoregulating drugs on the attachment of Haemophilus influenzae.
2001 Mar
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
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
S-carboxymethylcysteine inhibits the attachment of Streptococcus pneumoniae to human pharyngeal epithelial cells.
2003 Jun
Effect of glucose concentration on formation of AGEs in erythrocytes in vitro.
2005 Jun
Antioxidant therapies in COPD.
2006
Thiodiglycolic acid and dermatological reactions following S-carboxymethyl-L-cysteine administration.
2006 Feb
Cerebral formation in situ of S-carboxymethylcysteine after ifosfamide administration to mice: a further clue to the mechanism of ifosfamide encephalopathy.
2006 Mar 1
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
Glutaraldehyde is an effective cross-linker for production of antibodies against advanced glycation end-products.
2008 May 20
Phenylalanine 4-monooxygenase and the role of endobiotic metabolism enzymes in xenobiotic biotransformation.
2009 Oct
Association between lung function and exacerbation frequency in patients with COPD.
2010 Dec 9
Isoprostanes-biomarkers of lipid peroxidation: their utility in evaluating oxidative stress and analysis.
2010 Nov 17
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
L-carbocisteine [WHO-DD]
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
LJ206
Code English
Classification Tree Code System Code
WHO-VATC QR05CB03
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NCI_THESAURUS C74536
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WHO-ATC R05CB03
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Code System Code Type Description
ECHA (EC/EINECS)
211-327-5
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PRIMARY
RXCUI
2023
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PRIMARY RxNorm
ChEMBL
CHEMBL396416
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PRIMARY
CAS
638-23-3
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PRIMARY
EVMPD
SUB11790MIG
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SMS_ID
100000092161
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DAILYMED
740J2QX53R
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INN
2884
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EVMPD
SUB21966
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DRUG CENTRAL
4160
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PRIMARY
MESH
D002233
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CHEBI
16163
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PRIMARY
NCI_THESAURUS
C83591
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PRIMARY
EPA CompTox
DTXSID30110060
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DRUG BANK
DB04339
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PRIMARY
MERCK INDEX
m3072
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PRIMARY Merck Index
WIKIPEDIA
CARBOCISTEINE
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PRIMARY
NSC
14156
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PRIMARY
PUBCHEM
193653
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PRIMARY
FDA UNII
740J2QX53R
Created by admin on Fri Dec 15 15:16:17 GMT 2023 , Edited by admin on Fri Dec 15 15:16:17 GMT 2023
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