Chemical Component Summary

NameCARBOXYMETHYLATED CYSTEINE
Identifiers(2R)-2-amino-3-(carboxymethylsulfanyl)propanoic acid
FormulaC5 H9 N O4 S
Molecular Weight179.194
TypeL-PEPTIDE LINKING
Isomeric SMILESC([C@@H](C(=O)O)N)SCC(=O)O
InChIInChI=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
InChIKeyGBFLZEXEOZUWRN-VKHMYHEASA-N

Chemical Details

Formal Charge0
Atom Count20
Chiral Atom Count1
Bond Count19
Aromatic Bond Count0

Drug Info: DrugBank

DrugBank IDDB04339 
NameCarbocisteine
Groups
  • approved
  • investigational
DescriptionDyspnea and cough are common symptoms of chronic obstructive pulmonary disease (COPD)[A231169] and other respiratory conditions characterized by increased mucus production. Individuals with COPD have a greater risk of pulmonary infection due to the growth and accumulation of viruses and bacteria in thick bronchial mucus. Carbocisteine is a mucolytic drug that alleviates respiratory symptoms and infections by reducing the viscosity of mucus, allowing it to be expelled.[L32383] Several licenses for this drug were withdrawn following serious and fatal paradoxical effects after carbocisteine therapy in children; respiratory dress, dyspnea, and cough aggravation were reported by physicians in France and Italy.[A230993] Carbocisteine is currently not FDA or Health Canada approved, but is approved for use in Asia, Europe, and South America.
Synonyms
  • S-(carboxymethyl)-(R)-cysteine
  • L-3-((carboxymethyl)thio)alanine
  • S-carboxymethylcysteine
  • Carbocisteine lysine
  • (L)-2-Amino-3-(carboxymethylthio)propionic acid
IndicationCarbocisteine is indicated over the counter and in prescription formulas to clear airway secretions in conditions associated with increased mucus.[L24484,L24984,L20019]
Categories
  • Amino Acids
  • Amino Acids, Dicarboxylic
  • Amino Acids, Neutral
  • Amino Acids, Peptides, and Proteins
  • Amino Acids, Sulfur
ATC-CodeR05CB03
CAS number638-23-3

Drug Targets

NameTarget SequencePharmacological ActionActions
PI-PLC X domain-containing protein 3MASSQGKNELKLADWMATLPESMHSIPLTNLAIPGSHDSFSFYIDEASPV...unknowninhibitor
Lactosylceramide alpha-2,3-sialyltransferaseMRTKAAGCAERRPLQPRTEAAAAPAGRAMPSEYTYVKLRSDCSRPSLQWY...unknowninducer
Cysteine dioxygenase type 1MEQTEVLKPRTLADLIRILHQLFAGDEVNVEEVQAIMEAYESDPTEWAMY...unknownsubstrate
Phenylalanine-4-hydroxylaseMSTAVLENPGLGRKLSDFGQETSYIEDNCNQNGAISLIFSLKEEVGALAK...unknownsubstrate
Lactosylceramide alpha-2,3-sialyltransferaseMRTKAAGCAERRPLQPRTEAAAAPAGRAMPSEYTYVKLRSDCSRPSLQWY...unknowninducer
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 193653
ChEMBL CHEMBL396416
ChEBI CHEBI:16163