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Details

Stereochemistry ABSOLUTE
Molecular Formula C5H7NO4S.Na.H
Molecular Weight 201.176
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CARBOCYSTEINE SODIUM

SMILES

[H+].[Na+].N[C@@H](CSCC([O-])=O)C([O-])=O

InChI

InChIKey=DVTIFKUGQNCIGH-DFWYDOINSA-M
InChI=1S/C5H9NO4S.Na/c6-3(5(9)10)1-11-2-4(7)8;/h3H,1-2,6H2,(H,7,8)(H,9,10);/q;+1/p-1/t3-;/m0./s1

HIDE SMILES / InChI
Molecular Formula C5H7NO4S
Molecular Weight 177.178
Charge -2
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED
Molecular Formula H
Molecular Weight 1.0079
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

CNS Active
3913
Curator's Comment: Carbocysteine is CNS active in animals. No human data available,

Approval Year

2008
174
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Modulator
828
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
Carbocisteine

Approved Use

Carbocisteine is a mucolytic agent for the adjunctive therapy of respiratory tract disorders characterised by excessive, viscous mucus, including chronic obstructive airways disease.
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
Effect of fudosteine, a cysteine derivative, on blood flow of tracheal microvasculature increased by airway inflammation.
2001 Jul
Antioxidant activity of carbocysteine lysine salt monohydrate.
2001 Sep
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
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
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
Cerebral formation in situ of S-carboxymethylcysteine after ifosfamide administration to mice: a further clue to the mechanism of ifosfamide encephalopathy.
2006 Mar 1
Evidence for inactivation of cysteine proteases by reactive carbonyls via glycation of active site thiols.
2006 Sep 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
S-CMC-Lys protective effects on human respiratory cells during oxidative stress.
2008
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
Phenylalanine 4-monooxygenase and the role of endobiotic metabolism enzymes in xenobiotic biotransformation.
2009 Oct
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

Patents

JP2000256192A
4
WO1996035452A1
4

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
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:57:09 GMT 2023
Edited
by admin
on Fri Dec 15 18:57:09 GMT 2023
Record UNII
2UZV9PEJ2N
Record Status Validated (UNII)
Record Version
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Name Type Language
CARBOCYSTEINE SODIUM
Common Name English
CARBOCISTEINE SODIUM
MART.   WHO-DD  
Common Name English
CARBOCISTEINE SODIUM [MART.]
Common Name English
SODIUM 2-((2R)-2-AMINO-3-HYDROXY-3-OXOPROPYL)SULFANYLACETATE
Systematic Name English
Carbocisteine sodium [WHO-DD]
Common Name English
L-CYSTEINE, S-(CARBOXYMETHYL)-, MONOSODIUM SALT
Common Name English
Code System Code Type Description
PUBCHEM
23674719
Created by admin on Fri Dec 15 18:57:09 GMT 2023 , Edited by admin on Fri Dec 15 18:57:09 GMT 2023
PRIMARY
EVMPD
SUB01047MIG
Created by admin on Fri Dec 15 18:57:09 GMT 2023 , Edited by admin on Fri Dec 15 18:57:09 GMT 2023
PRIMARY
FDA UNII
2UZV9PEJ2N
Created by admin on Fri Dec 15 18:57:09 GMT 2023 , Edited by admin on Fri Dec 15 18:57:09 GMT 2023
PRIMARY
SMS_ID
100000084852
Created by admin on Fri Dec 15 18:57:09 GMT 2023 , Edited by admin on Fri Dec 15 18:57:09 GMT 2023
PRIMARY
Related Record Type Details
Structure of CARBOCYSTEINE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of CARBOCYSTEINE
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