Carbocisteine is a mucolytic that reduces the viscosity of sputum and so can be used to help relieve the symptoms of chronic obstructive pulmonary disorder (COPD) and bronchiectasis by allowing the sufferer to bring up sputum more easily. Carbocisteine should not be used with antitussives (cough suppressants) or medicines that dry up bronchial secretions.
CAT No: 10-101-113
CAS No:638-23-3
Synonyms/Alias:(R)-2-Amino-3-carboxymethylsulfanylpropionic acid; 3-[(Carboxymethyl)thio]alanine; AHR-3053; S-(Carboxymethyl)-L-cysteine; LJ-206; Carbocisteine; Carbocistein; Carbocysteine; DF 1794Y; Mucofan; PectDrill; Reomucil; Superthiol sirup; NSC 14156; NSC-14156; NSC14156;S-Carboxymethyl-L-cysteine
Chemical Name:(2R)-2-amino-3-(carboxymethylsulfanyl)propanoic acid
Carbocysteine is a sulfur-containing amino acid derivative classified as a mucolytic agent and a thioether analog of cysteine. Structurally, it features a carboxymethyl group attached to the amino acid backbone, imparting distinctive physicochemical properties that influence its biological interactions. In biochemical research, carbocysteine is valued for its ability to modulate disulfide bonds in glycoproteins, affecting the viscosity and rheological properties of biological fluids. Its unique chemical structure and reactivity profile make it a useful tool in studies involving sulfur metabolism, protein chemistry, and the investigation of oxidative processes. As a non-proteinogenic amino acid, carbocysteine serves as a model compound for exploring post-translational modifications, redox biology, and enzymatic mechanisms in vitro.
Mucolytic research: Carbocysteine is extensively employed in studies focusing on the biochemistry of mucus regulation and mucin structure. Its capacity to cleave and rearrange disulfide bridges within mucin glycoproteins is of particular interest to researchers investigating the molecular basis of mucolysis. By reducing mucin viscosity, it provides a model for understanding how chemical agents alter the physical properties of mucus at the molecular level, facilitating the analysis of mucociliary clearance and secretion dynamics in respiratory and gastrointestinal systems.
Redox biology investigations: The thioether moiety in carbocysteine renders it a valuable substrate for probing redox reactions and thiol-disulfide exchange processes in biological systems. Researchers utilize this compound to dissect the mechanisms of oxidative stress, antioxidant defense, and the modulation of reactive oxygen species in various experimental models. Its application extends to the evaluation of cellular responses to oxidative environments, supporting the elucidation of redox-sensitive signaling pathways and the identification of novel antioxidant strategies.
Protein modification and enzymology: Carbocysteine's structural similarity to cysteine, combined with its unique functional group, enables its use in studies of protein modification, particularly in the context of S-substitution and enzymatic specificity. It serves as a tool for investigating the activity and selectivity of enzymes such as transaminases, oxidases, and transferases involved in sulfur amino acid metabolism. By acting as an alternative substrate or inhibitor, it assists in mapping enzyme active sites and elucidating mechanistic details of catalysis involving sulfur-containing amino acids.
Analytical chemistry and standardization: In analytical laboratories, carbocysteine is utilized as a reference compound and calibration standard in chromatographic and spectrometric assays targeting sulfur-containing metabolites. Its well-defined chemical characteristics support the development and validation of quantitative methods for amino acid profiling, metabolomic studies, and quality control of biochemical reagents. The compound's stability and detectability make it suitable for use in method optimization and inter-laboratory comparisons.
Cell culture and metabolic studies: Researchers incorporate carbocysteine into cell culture systems to examine its effects on cellular metabolism, particularly in relation to sulfur amino acid pathways. Its presence can influence glutathione synthesis, modulate cellular redox status, and affect the uptake and utilization of related metabolites. These properties are exploited in metabolic flux analyses, nutrient supplementation experiments, and investigations into the regulation of cellular antioxidant capacity, providing insights into fundamental aspects of cell biology and metabolic adaptation.
Carbocysteine is a muco-active drug with free radical scavenging and anti-inflammatory properties. It is actually approved for clinical use as adjunctive therapy of respiratory tract disorders characterized by excessive, viscous mucus, including chronic obstructive airways disease (COPD).
Macciò, A., Madeddu, C., Panzone, F., & Mantovani, G. (2009). Carbocysteine: clinical experience and new perspectives in the treatment of chronic inflammatory diseases. Expert opinion on pharmacotherapy, 10(4), 693-703.
Cough, one of the main symptoms of bronchial asthma, is a chronic airway inflammatory disease with functionally damaged bronchial epithelium. Recently, we established an animal model with cough hypersensitivity after antigen challenge and clearly showed the protective effect of carbocysteine in this model. This study was designed to investigate the clinical effect of carbocysteine for cough sensitivity in patients with bronchial asthma.
Ishiura, Y., Fujimura, M., Yamamori, C., Nobata, K., Myou, S., Kurashima, K., ... & Takegoshi, T. (2003). Effect of carbocysteine on cough reflex to capsaicin in asthmatic patients. British journal of clinical pharmacology, 55(6), 504-510.
The aim of the study was to examine the effects of a mucolytic drug, carbocisteine, on rhinovirus (RV) infection in the airways. Human tracheal epithelial cells were infected with a major-group RV, RV14. RV14 infection increased virus titres and the cytokine content of supernatants. Carbocisteine reduced supernatant virus titres, the amount of RV14 RNA in cells, cell susceptibility to RV infection and supernatant cytokine concentrations, including interleukin (IL)-6 and IL-8, after RV14 infection. Carbocisteine reduced the expression of mRNA encoding intercellular adhesion molecule (ICAM)-1, the receptor for the major group of RVs. It also reduced the supernatant concentration of a soluble form of ICAM-1, the number and fluorescence intensity of acidic endosomes in the cells before RV infection, and nuclear factor-kappaB activation by RV14. Carbocisteine also reduced the supernatant virus titres of the minor group RV, RV2, although carbocisteine did not reduce the expression of mRNA encoding a low density lipoprotein receptor, the receptor for RV2. These results suggest that carbocisteine inhibits rhinovirus 2 infection by blocking rhinovirus RNA entry into the endosomes, and inhibits rhinovirus 14 infection by the same mechanism as well as by reducing intercellular adhesion molecule-1 levels. Carbocisteine may modulate airway inflammation by reducing the production of cytokines in rhinovirus infection.
Yasuda, H., Yamaya, M., Sasaki, T., Inoue, D., Nakayama, K., Yamada, M., ... & Sasaki, H. (2006). Carbocisteine inhibits rhinovirus infection in human tracheal epithelial cells. European Respiratory Journal, 28(1), 51-58.
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