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Details

Stereochemistry ABSOLUTE
Molecular Formula C6H14N2O2.C5H9NO4S.H2O
Molecular Weight 343.397
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CARBOCYSTEINE LYSINE MONOHYDRATE

SMILES

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

InChI

InChIKey=QVJUWKMADMJHJZ-PBUQCQDLSA-N
InChI=1S/C6H14N2O2.C5H9NO4S.H2O/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);1H2/t5-;3-;/m00./s1

HIDE SMILES / InChI
Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C5H9NO4S
Molecular Weight 179.194
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED
Molecular Formula C6H14N2O2
Molecular Weight 146.1876
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

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
Study about the inhibition of L-cysteine derivatives of nucleic acid bases in protein production.
2001
Study on the inhibition of protein production by L-cysteine derivatives of nucleic acid bases.
2002
Prolonged survival after experimental paraquat intoxication: role of alternative antioxidants.
2002 Feb
Thirty-five cases of S-carboxymethylcysteine use in paraquat poisoning.
2003 Feb
Phenylalanine 4-monooxygenase and the S-oxidation of S-carboxymethyl-L-cysteine.
2004
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
Reduced airway inflammation and remodeling in parallel with mucin 5AC protein expression decreased by s-carboxymethylcysteine, a mucoregulant, in the airways of rats exposed to sulfur dioxide.
2004 Aug
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
Exhaled Interleukine-6 and 8-isoprostane in chronic obstructive pulmonary disease: effect of carbocysteine lysine salt monohydrate (SCMC-Lys).
2004 Nov 28
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
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
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
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
Human phenylalanine monooxygenase and thioether metabolism.
2009 Jan
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
The effect and mechanism of action of carbocysteine on airway bacterial load in rats chronically exposed to cigarette smoke.
2010 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 Sat Dec 16 04:57:59 GMT 2023
Edited
by admin
on Sat Dec 16 04:57:59 GMT 2023
Record UNII
QA5ZP9OL3E
Record Status Validated (UNII)
Record Version
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Name Type Language
CARBOCYSTEINE LYSINE MONOHYDRATE
Common Name English
SCMC-LYS
Common Name English
CARBOCYSTEINE LYSINE SALT MONOHYDRATE
Common Name English
L-LYSINE, COMPD. WITH S-(CARBOXYMETHYL)-L-CYSTEINE (1:1), MONOHYDRATE
Common Name English
FLUIFORT
Brand Name English
Code System Code Type Description
CAS
151756-26-2
Created by admin on Sat Dec 16 04:57:59 GMT 2023 , Edited by admin on Sat Dec 16 04:57:59 GMT 2023
PRIMARY
EVMPD
SUB127327
Created by admin on Sat Dec 16 04:57:59 GMT 2023 , Edited by admin on Sat Dec 16 04:57:59 GMT 2023
PRIMARY
FDA UNII
QA5ZP9OL3E
Created by admin on Sat Dec 16 04:57:59 GMT 2023 , Edited by admin on Sat Dec 16 04:57:59 GMT 2023
PRIMARY
RXCUI
1793898
Created by admin on Sat Dec 16 04:57:59 GMT 2023 , Edited by admin on Sat Dec 16 04:57:59 GMT 2023
PRIMARY
SMS_ID
100000153359
Created by admin on Sat Dec 16 04:57:59 GMT 2023 , Edited by admin on Sat Dec 16 04:57:59 GMT 2023
PRIMARY
DAILYMED
QA5ZP9OL3E
Created by admin on Sat Dec 16 04:57:59 GMT 2023 , Edited by admin on Sat Dec 16 04:57:59 GMT 2023
PRIMARY
EPA CompTox
DTXSID90164867
Created by admin on Sat Dec 16 04:57:59 GMT 2023 , Edited by admin on Sat Dec 16 04:57:59 GMT 2023
PRIMARY
PUBCHEM
71587532
Created by admin on Sat Dec 16 04:57:59 GMT 2023 , Edited by admin on Sat Dec 16 04:57:59 GMT 2023
PRIMARY
Related Record Type Details
Structure of CARBOCYSTEINE LYSINE
ANHYDROUS->SOLVATE
Structure of LYSINE
PARENT -> SALT/SOLVATE
Structure of CARBOCYSTEINE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of CARBOCYSTEINE
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