CARBOCYSTEINE

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 160 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 8297
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 828
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 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Chronic obstructive pulmonary disease 174 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 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

Title	Date	PubMed
Effect of fudosteine, a cysteine derivative, on blood flow of tracheal microvasculature increased by airway inflammation.	2001 Jul	21782562
Prolonged survival after experimental paraquat intoxication: role of alternative antioxidants.	2002 Feb	11824777
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	14567291
Chemical modification of muscle protein in diabetes.	2004 May 15	15111128
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
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	16097796
Protein and low molecular mass thiols as targets and inhibitors of glycation reactions.	2006 Dec	17173381
S-CMC-Lys-dependent stimulation of electrogenic glutathione secretion by human respiratory epithelium.	2006 Jan	16283140
Antioxidant therapeutic targets in COPD.	2006 Jun	16787173
Cerebral formation in situ of S-carboxymethylcysteine after ifosfamide administration to mice: a further clue to the mechanism of ifosfamide encephalopathy.	2006 Mar 1	16229978
Mechanisms for the proton mobility-dependent gas-phase fragmentation reactions of S-alkyl cysteine sulfoxide-containing peptide ions.	2007 Sep	17689096
Human phenylalanine monooxygenase and thioether metabolism.	2009 Jan	19126298
The pharmacokinetics of orally administered S-carboxymethyl-L-cysteine in the dog, calf and sheep.	2010 Feb 19	20035864
Comparative metabolism of cyclophosphamide and ifosfamide in the mouse using UPLC-ESI-QTOFMS-based metabolomics.	2010 Oct 1	20541539

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 `Fri Dec 15 15:16:17 GMT 2023` Edited by `admin` on `Fri Dec 15 15:16:17 GMT 2023`
Record UNII	740J2QX53R
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CARBOCYSTEINE

Official Name

English

MUCOLASE

Brand Name

English

3-[(Carboxymethyl)thio]alanine

Systematic Name

English

CARBOCISTEINE

Official Name

English

PECTOX

Brand Name

English

CARBOCISTEIN

Common Name

English

CARBOCIT

Brand Name

English

NSC-14156

Code

English

CARBOCYSTEINE [INCI]

Common Name

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