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
S-carboxymethylcysteine in the treatment of glue ear: quantitative systematic review.	2001	11580867
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	11714908
Study on the inhibition of protein production by L-cysteine derivatives of nucleic acid bases.	2002	12903126
Prolonged survival after experimental paraquat intoxication: role of alternative antioxidants.	2002 Feb	11824777
Chemical modification of muscle protein in diabetes.	2004 May 15	15111128
N-acetylcysteine inhibits Na+ absorption across human nasal epithelial cells.	2004 Oct	15281093
Analysis of plasma amino acids by HPLC with photodiode array and fluorescence detection.	2005 Apr	15748603
Antioxidant therapeutic targets in COPD.	2006 Jun	16787173
Phenylalanine 4-monooxygenase and the S-oxidation of S-carboxymethyl-L-cysteine by human cytosolic fractions.	2008	19326770
S-CMC-Lys protective effects on human respiratory cells during oxidative stress.	2008	19088427
Immunological detection of N omega-(Carboxymethyl)arginine by a specific antibody.	2008 Apr	18079475
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
Mouse recombinant phenylalanine monooxygenase and the S-oxygenation of thioether substrates.	2009 Mar-Apr	19367645
Phenylalanine 4-monooxygenase and the role of endobiotic metabolism enzymes in xenobiotic biotransformation.	2009 Oct	19653802
Modulation of the cellular expression of circulating advanced glycation end-product receptors in type 2 diabetic nephropathy.	2010	21318189
Association between lung function and exacerbation frequency in patients with COPD.	2010 Dec 9	21191438
The pharmacokinetics of orally administered S-carboxymethyl-L-cysteine in the dog, calf and sheep.	2010 Feb 19	20035864
The effect and mechanism of action of carbocysteine on airway bacterial load in rats chronically exposed to cigarette smoke.	2010 Oct	20807377
Comparative metabolism of cyclophosphamide and ifosfamide in the mouse using UPLC-ESI-QTOFMS-based metabolomics.	2010 Oct 1	20541539
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	20599776

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