CARBOCYSTEINE

Possibly Marketed Outside US

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 Search

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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20956181
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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Oxidative Stress 162 Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19239402 \| https://www.ncbi.nlm.nih.gov/pubmed/20956181 \| https://www.ncbi.nlm.nih.gov/pubmed/19281081	Inhibitor 8504
regulation of mucus secretion 4 Target ID: GO:0070255 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19239402 \| https://www.ncbi.nlm.nih.gov/pubmed/20956181 \| https://www.ncbi.nlm.nih.gov/pubmed/19281081	Modulator 846
inflammatory response 47 Target ID: GO:0006954 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19239402 \| https://www.ncbi.nlm.nih.gov/pubmed/20956181 \| https://www.ncbi.nlm.nih.gov/pubmed/19281081	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Chronic obstructive pulmonary disease 175 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20956181 https://www.ncbi.nlm.nih.gov/pubmed/18555912 https://www.ncbi.nlm.nih.gov/pubmed/19281081	Primary		Approved 8583	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.

C_max

Value	Dose	Analyte	Population
13.38 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7139067/	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16724543/	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 EXPERIMENT https://scholar.google.com/scholar?cluster=7613016307870987923&hl=ja&as_sdt=0,33	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

Value	Dose	Analyte	Population
63.15 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7139067/	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16724543/	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 EXPERIMENT https://scholar.google.com/scholar?cluster=7613016307870987923&hl=ja&as_sdt=0,33	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

T_1/2

Value	Dose	Analyte	Population
2.05 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7139067/	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16724543/	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 EXPERIMENT https://scholar.google.com/scholar?cluster=7613016307870987923&hl=ja&as_sdt=0,33	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

Dose	Population	Adverse 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: https://pubmed.ncbi.nlm.nih.gov/365537/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/365537/	Sources: https://pubmed.ncbi.nlm.nih.gov/365537/
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: https://pubmed.ncbi.nlm.nih.gov/8739489/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8739489/	Sources: https://pubmed.ncbi.nlm.nih.gov/8739489/

PubMed

Title	Date	PubMed
Association between lung function and exacerbation frequency in patients with COPD.	2010-12-09	21191438
Isoprostanes-biomarkers of lipid peroxidation: their utility in evaluating oxidative stress and analysis.	2010-11-17	21151461
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.	2010-10-15	20599776
Comparative metabolism of cyclophosphamide and ifosfamide in the mouse using UPLC-ESI-QTOFMS-based metabolomics.	2010-10-01	20541539
The effect and mechanism of action of carbocysteine on airway bacterial load in rats chronically exposed to cigarette smoke.	2010-10	20807377
The pharmacokinetics of orally administered S-carboxymethyl-L-cysteine in the dog, calf and sheep.	2010-02-19	20035864
Modulation of the cellular expression of circulating advanced glycation end-product receptors in type 2 diabetic nephropathy.	2010	21318189
Phenylalanine 4-monooxygenase and the role of endobiotic metabolism enzymes in xenobiotic biotransformation.	2009-10	19653802
Mouse recombinant phenylalanine monooxygenase and the S-oxygenation of thioether substrates.	2009-04-16	19367645
Human phenylalanine monooxygenase and thioether metabolism.	2009-01	19126298
The activity of wild type and mutant phenylalanine hydroxylase with respect to the C-oxidation of phenylalanine and the S-oxidation of S-carboxymethyl-L-cysteine.	2009-01	19036622
Measurement of phenylalanine monooxygenase (PAH) activities.	2009	23045014
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	19590597
Variation in the attachment of Streptococcus pneumoniae to human pharyngeal epithelial cells after treatment with S-carboxymethylcysteine.	2008-08	18709541
Glutaraldehyde is an effective cross-linker for production of antibodies against advanced glycation end-products.	2008-05-20	18353354
s-Carboxymethylcysteine inhibits carbachol-induced constriction of epithelium-denuded rat and human airway preparations.	2008-05	18215189
Usefulness of antibodies for evaluating the biological significance of AGEs.	2008-04	18079488
Immunological detection of N omega-(Carboxymethyl)arginine by a specific antibody.	2008-04	18079475
Immunochemical detection of Nepsilon-(carboxyethyl)lysine using a specific antibody.	2008-03-20	18242632
Influence of various combinations of mucolytic agent and non-ionic surfactant on intestinal absorption of poorly absorbed hydrophilic compounds.	2008-02-12	17869034
Phenylalanine 4-monooxygenase and the S-oxidation of S-carboxymethyl-L-cysteine by human cytosolic fractions.	2008	19326770
The role for S-carboxymethylcysteine (carbocisteine) in the management of chronic obstructive pulmonary disease.	2008	19281081
S-CMC-Lys protective effects on human respiratory cells during oxidative stress.	2008	19088427
The suppression of enhanced bitterness intensity of macrolide dry syrup mixed with an acidic powder.	2007-10	17917288
Mechanisms for the proton mobility-dependent gas-phase fragmentation reactions of S-alkyl cysteine sulfoxide-containing peptide ions.	2007-09	17689096
Reduction and s-carboxymethylation of proteins: large-scale method.	2007-02-01	21357011
Bacterial lysate in the prevention of acute exacerbation of COPD and in respiratory recurrent infections.	2007	18229572
Protein and low molecular mass thiols as targets and inhibitors of glycation reactions.	2006-12	17173381
Evidence for inactivation of cysteine proteases by reactive carbonyls via glycation of active site thiols.	2006-09-01	16671891
Antioxidant therapeutic targets in COPD.	2006-06	16787173
Efficacy of S-carboxymethyl-L-cysteine for otitis media with effusion.	2006-05	16771015
The sulphoxidation of S-carboxymethyl-L-cysteine in COPD.	2006-04	16585098
Cerebral formation in situ of S-carboxymethylcysteine after ifosfamide administration to mice: a further clue to the mechanism of ifosfamide encephalopathy.	2006-03-01	16229978
Thiodiglycolic acid and dermatological reactions following S-carboxymethyl-L-cysteine administration.	2006-02	16433823
Synergistic effect of interleukin 1 alpha on nontypeable Haemophilus influenzae-induced up-regulation of human beta-defensin 2 in middle ear epithelial cells.	2006-01-24	16433908
S-CMC-Lys-dependent stimulation of electrogenic glutathione secretion by human respiratory epithelium.	2006-01	16283140
Antioxidant therapies in COPD.	2006	18046899
S-carboxymethylcysteine normalises airway responsiveness in sensitised and challenged mice.	2005-10	16204586
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.	2005-08	16097796
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.	2005-07-25	16022542
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.	2005-07	16029368
Effect of glucose concentration on formation of AGEs in erythrocytes in vitro.	2005-06	16037233
Analysis of plasma amino acids by HPLC with photodiode array and fluorescence detection.	2005-04	15748603
Induction of cysteine dioxygenase activity by oral administration of cysteine analogues to the rat: implications for drug efficacy and safety.	2005	16355974
Phenylalanine 4-monooxygenase and the S-oxidation of S-carboxymethyl-L-cysteine in HepG2 cells.	2005	16086552
Phenylalanine hydroxylase: possible involvement in the S-oxidation of S-carboxymethyl-l-cysteine.	2004-12-01	15519575
Exhaled Interleukine-6 and 8-isoprostane in chronic obstructive pulmonary disease: effect of carbocysteine lysine salt monohydrate (SCMC-Lys).	2004-11-28	15556150
Cancer-related anorexia/cachexia syndrome and oxidative stress: an innovative approach beyond current treatment.	2004-10	15466983
Phenylalanine 4-monooxygenase and the S-oxidation of S-carboxymethyl-L-cysteine.	2004	15508431
Effect of fudosteine, a cysteine derivative, on blood flow of tracheal microvasculature increased by airway inflammation.	2001-07	21782562

Patents

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 `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

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Name

Type

Language

CARBOCISTEINE

Preferred Name

English

CARBOCYSTEINE

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

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

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