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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

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

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

Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
13.38 mg/L
1.5 g single, oral
dose: 1.5 g
route of administration: Oral
experiment type: SINGLE
co-administered:
CARBOCYSTEINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
8.02 μg/mL
750 mg single, oral
dose: 750 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CARBOCYSTEINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
5.6 μg/mL
1000 mg single, oral
dose: 1000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CARBOCYSTEINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
63.15 mg × h/L
1.5 g single, oral
dose: 1.5 g
route of administration: Oral
experiment type: SINGLE
co-administered:
CARBOCYSTEINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
14.88 μg × h/mL
750 mg single, oral
dose: 750 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CARBOCYSTEINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
22.8 μg × h/mL
1000 mg single, oral
dose: 1000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CARBOCYSTEINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.05 h
1.5 g single, oral
dose: 1.5 g
route of administration: Oral
experiment type: SINGLE
co-administered:
CARBOCYSTEINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
2.02 h
750 mg single, oral
dose: 750 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CARBOCYSTEINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
1.5 h
1000 mg single, oral
dose: 1000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CARBOCYSTEINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
3 g 1 times / day multiple, oral
Highest studied dose
Dose: 3 g, 1 times / day
Route: oral
Route: multiple
Dose: 3 g, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
2.7 g 1 times / day multiple, oral
Studied dose
Dose: 2.7 g, 1 times / day
Route: oral
Route: multiple
Dose: 2.7 g, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
PubMed

PubMed

TitleDatePubMed
S-carboxymethylcysteine in the treatment of glue ear: quantitative systematic review.
2001
Insights into the mechanisms of ifosfamide encephalopathy: drug metabolites have agonistic effects on alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA)/kainate receptors and induce cellular acidification in mouse cortical neurons.
2001 Dec
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
Chemical modification of muscle protein in diabetes.
2004 May 15
N-acetylcysteine inhibits Na+ absorption across human nasal epithelial cells.
2004 Oct
Analysis of plasma amino acids by HPLC with photodiode array and fluorescence detection.
2005 Apr
Antioxidant therapeutic targets in COPD.
2006 Jun
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
Immunological detection of N omega-(Carboxymethyl)arginine by a specific antibody.
2008 Apr
Sequestration of Alkyltin(IV) compounds in aqueous solution: formation, stability, and empirical relationships for the binding of dimethyltin(IV) cation by N- and O-donor ligands.
2009
Mouse recombinant phenylalanine monooxygenase and the S-oxygenation of thioether substrates.
2009 Mar-Apr
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
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

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
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:52:19 GMT 2025
Edited
by admin
on Mon Mar 31 17:52:19 GMT 2025
Record UNII
740J2QX53R
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CARBOCISTEINE
EP   INN   MART.  
INN  
Preferred Name English
CARBOCYSTEINE
INCI   MI   USAN  
USAN   INCI  
Official Name English
MUCOLASE
Brand Name English
3-[(Carboxymethyl)thio]alanine
Systematic Name English
PECTOX
Brand Name English
CARBOCISTEIN
Common Name English
CARBOCIT
Brand Name English
NSC-14156
Code 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
Created by admin on Mon Mar 31 17:52:19 GMT 2025 , Edited by admin on Mon Mar 31 17:52:19 GMT 2025
NCI_THESAURUS C74536
Created by admin on Mon Mar 31 17:52:19 GMT 2025 , Edited by admin on Mon Mar 31 17:52:19 GMT 2025
WHO-ATC R05CB03
Created by admin on Mon Mar 31 17:52:19 GMT 2025 , Edited by admin on Mon Mar 31 17:52:19 GMT 2025
Code System Code Type Description
ECHA (EC/EINECS)
211-327-5
Created by admin on Mon Mar 31 17:52:19 GMT 2025 , Edited by admin on Mon Mar 31 17:52:19 GMT 2025
PRIMARY
RXCUI
2023
Created by admin on Mon Mar 31 17:52:19 GMT 2025 , Edited by admin on Mon Mar 31 17:52:19 GMT 2025
PRIMARY RxNorm
ChEMBL
CHEMBL396416
Created by admin on Mon Mar 31 17:52:19 GMT 2025 , Edited by admin on Mon Mar 31 17:52:19 GMT 2025
PRIMARY
CAS
638-23-3
Created by admin on Mon Mar 31 17:52:19 GMT 2025 , Edited by admin on Mon Mar 31 17:52:19 GMT 2025
PRIMARY
EVMPD
SUB11790MIG
Created by admin on Mon Mar 31 17:52:19 GMT 2025 , Edited by admin on Mon Mar 31 17:52:19 GMT 2025
PRIMARY
SMS_ID
100000092161
Created by admin on Mon Mar 31 17:52:19 GMT 2025 , Edited by admin on Mon Mar 31 17:52:19 GMT 2025
PRIMARY
DAILYMED
740J2QX53R
Created by admin on Mon Mar 31 17:52:19 GMT 2025 , Edited by admin on Mon Mar 31 17:52:19 GMT 2025
PRIMARY
INN
2884
Created by admin on Mon Mar 31 17:52:19 GMT 2025 , Edited by admin on Mon Mar 31 17:52:19 GMT 2025
PRIMARY
EVMPD
SUB21966
Created by admin on Mon Mar 31 17:52:19 GMT 2025 , Edited by admin on Mon Mar 31 17:52:19 GMT 2025
PRIMARY
DRUG CENTRAL
4160
Created by admin on Mon Mar 31 17:52:19 GMT 2025 , Edited by admin on Mon Mar 31 17:52:19 GMT 2025
PRIMARY
MESH
D002233
Created by admin on Mon Mar 31 17:52:19 GMT 2025 , Edited by admin on Mon Mar 31 17:52:19 GMT 2025
PRIMARY
CHEBI
16163
Created by admin on Mon Mar 31 17:52:19 GMT 2025 , Edited by admin on Mon Mar 31 17:52:19 GMT 2025
PRIMARY
NCI_THESAURUS
C83591
Created by admin on Mon Mar 31 17:52:19 GMT 2025 , Edited by admin on Mon Mar 31 17:52:19 GMT 2025
PRIMARY
EPA CompTox
DTXSID30110060
Created by admin on Mon Mar 31 17:52:19 GMT 2025 , Edited by admin on Mon Mar 31 17:52:19 GMT 2025
PRIMARY
DRUG BANK
DB04339
Created by admin on Mon Mar 31 17:52:19 GMT 2025 , Edited by admin on Mon Mar 31 17:52:19 GMT 2025
PRIMARY
MERCK INDEX
m3072
Created by admin on Mon Mar 31 17:52:19 GMT 2025 , Edited by admin on Mon Mar 31 17:52:19 GMT 2025
PRIMARY Merck Index
WIKIPEDIA
CARBOCISTEINE
Created by admin on Mon Mar 31 17:52:19 GMT 2025 , Edited by admin on Mon Mar 31 17:52:19 GMT 2025
PRIMARY
NSC
14156
Created by admin on Mon Mar 31 17:52:19 GMT 2025 , Edited by admin on Mon Mar 31 17:52:19 GMT 2025
PRIMARY
PUBCHEM
193653
Created by admin on Mon Mar 31 17:52:19 GMT 2025 , Edited by admin on Mon Mar 31 17:52:19 GMT 2025
PRIMARY
FDA UNII
740J2QX53R
Created by admin on Mon Mar 31 17:52:19 GMT 2025 , Edited by admin on Mon Mar 31 17:52:19 GMT 2025
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
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ACTIVE MOIETY