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Carbocisteine

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Carbocisteine
Carboxymethylcystein Formulae.png
Carbocisteine 3D.png
Names
IUPAC name
(R)-2-Amino-3-(carboxymethylsulfanyl)propanoic acid
Other names
S-Carboxymethyl-L-cysteine; Actithiol, Lisomucil, Muciclar, Mucodyne, Mucolex, Rhinathiol, Transbronchin
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.010.298
KEGG
PubChem CID
UNII
  • 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 checkY
    Key: GBFLZEXEOZUWRN-VKHMYHEASA-N checkY
  • InChI=1/C5H9NO4S/c6-3(5(9)10)1-11-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)
    Key: GBFLZEXEOZUWRN-UHFFFAOYAN
  • InChI=1/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
    Key: GBFLZEXEOZUWRN-VKHMYHEABX
  • O=C(O)C(N)CSCC(=O)O
  • O=C(O)[C@@H](N)CSCC(=O)O
Properties
C5H9NO4S
Molar mass 179.19 g·mol−1
Appearance Colorless solid
Melting point 204 to 207 °C (399 to 405 °F; 477 to 480 K)
Pharmacology
R05CB03 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Carbocisteine, also called carbocysteine, 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.

It was first described in 1951 and came into medical use in 1960. Carbocisteine is produced by alkylation of cysteine with chloroacetic acid.


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