Carbocisteine

• S -carboxymethyl -L-cysteine
• (R )-2- amino-4- thia- adipic acid
• L-2- amino-3- ( carboxymethylthio ) propionic acid
• 3 - ( carboxymethylthio ) -L-alanine
• L-3- [( carboxymethyl) thio] alanine
• L- carboxymethylcysteine
• (R ) - carbocisteine

R05CB03

White solid

Secretolytics

Fixed

206 ° C

Soluble in water

8400 mg · kg -1 ( LD50, mouse, oral)

Template: Infobox chemical / molecular formula search available

Carbocysteine ​​( international name carbocisteine ​​) is a chiral drug that is used as a mucolytic agent against tight cough, such as occurs for example in a bronchitis.

Action and Application

Carbocisteine ​​acts not by cleavage of the disulfide bonds of the secretion in the bronchi as acetylcysteine, but intracellularly: It is increasingly produces mucus thinner and less viscous mucus. Since the 1970s carbocysteine ​​is in the indications

• Acute or chronic bronchitis
• Asthma and emphysema
• Bronchiectasis
• Bronchopneumonia

Employed.

The effectiveness of carbocysteine ​​is controversial, some experts attribute the mucolytic effect on the increased intake of water back.

Properties

The specific optical rotation of carbocysteine ​​[ αD20 ] is 0.5 ° in 1 M hydrochloric acid.

Chemistry

Carbocysteine ​​is produced from chlorine and acetic acid of the natural α - amino acid is L -cysteine ​​by using sodium hydroxide solution, by a nucleophilic substitution reaction with elimination of the sodium chloride. Carbocisteine ​​is used exclusively in the enantiomerically pure L- form as a drug. S -carboxymethyl -L-cysteine ​​having the stereogenic center ( α - carbon atom of the cysteine ​​Substruktureinheit ) (R )-configuration. The resolution of DL- S -carboxymethyl- cysteine ​​is described in the literature.

Trade names

Mephathiol (CH), Mucoseptal (CH), Pectorex (CH), Rhinathiol (CH), Transbronchin (D), Tussantiol (CH)

Triofan (CH)