CCS

CARBOXYMETHYLATED CYSTEINE

Created:	1999-07-08
Last modified:	2024-09-27

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31 entries where CCS is found in a polymer sequence

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Chemical Details
Formal Charge	0
Atom Count	20
Chiral Atom Count	1
Bond Count	19
Aromatic Bond Count	0

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Chemical Component Summary
Name	CARBOXYMETHYLATED CYSTEINE
Systematic Name (OpenEye OEToolkits)	(2R)-2-amino-3-(carboxymethylsulfanyl)propanoic acid
Formula	C₅ H₉ N O₄ S
Molecular Weight	179.194
Type	L-PEPTIDE LINKING

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	10.04	O=C(O)C(N)CSCC(=O)O
SMILES	CACTVS	3.341	N[CH](CSCC(O)=O)C(O)=O
SMILES	OpenEye OEToolkits	1.5.0	C(C(C(=O)O)N)SCC(=O)O
Canonical SMILES	CACTVS	3.341	N[C@@H](CSCC(O)=O)C(O)=O
Canonical SMILES	OpenEye OEToolkits	1.5.0	C([C@@H](C(=O)O)N)SCC(=O)O
InChI	InChI	1.03	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
InChIKey	InChI	1.03	GBFLZEXEOZUWRN-VKHMYHEASA-N

Drug Info: DrugBank

DrugBank ID	DB04339
Name	Carbocisteine
Groups	approved investigational
Description	Dyspnea 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infections by reducing the viscosity of mucus, allowing it to be expelled.[L32383] Several licenses for this drug were withdrawn following serious and fatal paradoxical effects after carbocisteine therapy in children; respiratory dress, dyspnea, and cough aggravation were reported by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-carboxymethylcysteine (R)-S-(carboxymethyl)cysteine (L)-2-Amino-3-(carboxymethylthio)propionic acid L-3-((carboxymethyl)thio)alanine S-(carboxymethyl)-(R)-cysteine L-carbocysteine Carbocisteine lysine carbocisteína S-carboxymethyl-L-cysteine Carbocisteine
Indication	Carbocisteine 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 Anti-Infective Agents Anti-Infective Agents, Local Cough and Cold Preparations Cysteine Expectorants Respiratory System Agents Sulfhydryl Compounds Sulfur Compounds
ATC-Code	R05CB03
CAS number	638-23-3

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
PI-PLC X domain-containing protein 3	MASSQGKNELKLADWMATLPESMHSIPLTNLAIPGSHDSFSFYIDEASPV...	unknown	inhibitor
Lactosylceramide alpha-2,3-sialyltransferase	MRTKAAGCAERRPLQPRTEAAAAPAGRAMPSEYTYVKLRSDCSRPSLQWY...	unknown	inducer
Cysteine dioxygenase type 1	MEQTEVLKPRTLADLIRILHQLFAGDEVNVEEVQAIMEAYESDPTEWAMY...	unknown	substrate
Phenylalanine-4-hydroxylase	MSTAVLENPGLGRKLSDFGQETSYIEDNCNQNGAISLIFSLKEEVGALAK...	unknown	substrate
Lactosylceramide alpha-2,3-sialyltransferase	MRTKAAGCAERRPLQPRTEAAAAPAGRAMPSEYTYVKLRSDCSRPSLQWY...	unknown	inducer

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