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Details

Stereochemistry ABSOLUTE
Molecular Formula C6H14N2O2.C5H9NO4S
Molecular Weight 325.382
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CARBOCYSTEINE LYSINE

SMILES

NCCCC[C@H](N)C(O)=O.N[C@@H](CSCC(O)=O)C(O)=O

InChI

InChIKey=SAGXGPWVLUSDSQ-RVZXSAGBSA-N
InChI=1S/C6H14N2O2.C5H9NO4S/c7-4-2-1-3-5(8)6(9)10;6-3(5(9)10)1-11-2-4(7)8/h5H,1-4,7-8H2,(H,9,10);3H,1-2,6H2,(H,7,8)(H,9,10)/t5-;3-/m00/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
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
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
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
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
N-acetylcysteine inhibits Na+ absorption across human nasal epithelial cells.
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
S-carboxymethylcysteine normalises airway responsiveness in sensitised and challenged mice.
2005 Oct
Protein and low molecular mass thiols as targets and inhibitors of glycation reactions.
2006 Dec
S-CMC-Lys-dependent stimulation of electrogenic glutathione secretion by human respiratory epithelium.
2006 Jan
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
Bacterial lysate in the prevention of acute exacerbation of COPD and in respiratory recurrent infections.
2007
Phenylalanine 4-monooxygenase and the S-oxidation of S-carboxymethyl-L-cysteine by human cytosolic fractions.
2008
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
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
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 LYSINE
Common Name English
LYSINE CARBOCYSTEINATE
Common Name English
LYSINE CARBOXYMETHYL CYSTEINATE [INCI]
Common Name English
CARBOCISTEINE LYSINE [MART.]
Common Name English
Carbocisteine lysine [WHO-DD]
Common Name English
CARBOCISTEINE LYSINE
MART.   WHO-DD  
Common Name English
LYSINE CARBOXYMETHYL CYSTEINATE
INCI  
INCI  
Official Name English
CARBOCYSTEINE-LYSINE
Common Name English
L-LYSINE, COMPD. WITH S-(CARBOXYMETHYL)-L-CYSTEINE (1:1)
Systematic Name English
Code System Code Type Description
EVMPD
SUB01046MIG
Created by admin on Fri Dec 15 15:32:32 GMT 2023 , Edited by admin on Fri Dec 15 15:32:32 GMT 2023
PRIMARY
RXCUI
1427149
Created by admin on Fri Dec 15 15:32:32 GMT 2023 , Edited by admin on Fri Dec 15 15:32:32 GMT 2023
PRIMARY RxNorm
FDA UNII
1D1Y95PXXA
Created by admin on Fri Dec 15 15:32:32 GMT 2023 , Edited by admin on Fri Dec 15 15:32:32 GMT 2023
PRIMARY
PUBCHEM
6452154
Created by admin on Fri Dec 15 15:32:32 GMT 2023 , Edited by admin on Fri Dec 15 15:32:32 GMT 2023
PRIMARY
EPA CompTox
DTXSID60964336
Created by admin on Fri Dec 15 15:32:32 GMT 2023 , Edited by admin on Fri Dec 15 15:32:32 GMT 2023
PRIMARY
CAS
49673-81-6
Created by admin on Fri Dec 15 15:32:32 GMT 2023 , Edited by admin on Fri Dec 15 15:32:32 GMT 2023
PRIMARY
SMS_ID
100000090119
Created by admin on Fri Dec 15 15:32:32 GMT 2023 , Edited by admin on Fri Dec 15 15:32:32 GMT 2023
PRIMARY
DAILYMED
1D1Y95PXXA
Created by admin on Fri Dec 15 15:32:32 GMT 2023 , Edited by admin on Fri Dec 15 15:32:32 GMT 2023
PRIMARY
ECHA (EC/EINECS)
256-425-9
Created by admin on Fri Dec 15 15:32:32 GMT 2023 , Edited by admin on Fri Dec 15 15:32:32 GMT 2023
PRIMARY
EVMPD
SUB127326
Created by admin on Fri Dec 15 15:32:32 GMT 2023 , Edited by admin on Fri Dec 15 15:32:32 GMT 2023
ALTERNATIVE
DRUG CENTRAL
3892
Created by admin on Fri Dec 15 15:32:32 GMT 2023 , Edited by admin on Fri Dec 15 15:32:32 GMT 2023
PRIMARY