Carbocysteine

from Wikipedia, the free encyclopedia
Structural formula
Structure of carbocysteine
General
Non-proprietary name Carbocisteine
other names
  • 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
Molecular formula C 5 H 9 NO 4 S
Brief description

white solid

External identifiers / databases
CAS number 638-23-3
EC number 211-327-5
ECHA InfoCard 100.010.298
PubChem 193653
ChemSpider 168055
DrugBank DB04339
Wikidata Q423408
Drug information
ATC code

R05 CB03

Drug class

Secretolytics

properties
Molar mass 179.19 g mol −1
Physical state

firmly

Melting point

206 ° C

solubility

soluble in water

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
Toxicological data

8400 mg kg −1 ( LD 50 ,  mouse ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Carbocysteine ( international non- proprietary name Carbocistein ) is a chiral drug that is used as a mucolytic against stubborn coughs , such as those that occur in bronchitis .

Effect and use

Carbocisteine ​​does not work by splitting the disulfide bridges of the secretion in the bronchi like acetylcysteine , but rather intracellularly: more thin-flowing mucus is produced and less viscous mucus. Carbocysteine ​​has been one of the indications since the 1970s

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

used.

The effectiveness of carbocysteine ​​is controversial, some experts attribute the expectorant effect to the increased consumption of water.

properties

The specific rotation value of carbocysteine ​​[α D 20 ] is 0.5 ° in 1 M hydrochloric acid .

chemistry

Manufacturing

Carbocysteine ​​is made from chloroacetic acid and the natural α- amino acid L - cysteine with the help of sodium hydroxide solution through a nucleophilic substitution reaction with the elimination of sodium chloride.

Isomerism

Carbocisteine ​​is used exclusively in the enantiomerically pure L form as a medicinal substance. S -carboxymethyl- L -cysteine ​​has ( R ) configuration at the stereogenic center (α-carbon atom of the cysteine ​​substructure unit) .

The resolution of S -carboxymethyl- DL- cysteine ​​is described in the literature.

Trade names

Monopreparations

Mephathiol (CH), Mucoseptal (CH), Pectorex (CH), Rhinathiol (CH), Transbronchin (D), Tussantiol (CH), Siroxyl (B / L)

Combination preparations

Triofan (CH)

Individual evidence

  1. ↑ a b Data sheet S-Carboxymethyl-L-cysteine (PDF) from Fisher Scientific , accessed on February 13, 2014.
  2. ↑ a b Entry on carbocysteine in the ChemIDplus database of the United States National Library of Medicine (NLM) .
  3. ↑ S-carboxymethyl-L-cysteine data sheet from Sigma-Aldrich , accessed on April 27, 2011 ( PDF ).
  4. ↑ B. Staffeld: Studies on the metabolism of carbocysteine ​​in humans. Dissertation, FU Berlin, 1993. DNB 931876559
  5. ^ Axel Kleemann , Jürgen Engel, Bernd Kutscher and Dieter Reichert: Pharmaceutical Substances. 4th edition (2000), Thieme-Verlag Stuttgart, page 346, ISBN 978-1-58890-031-9 .
  6. ↑ Axel Kleemann and Jürgen Martens : Optical Resolution of Racemic S- (Carboxymethyl) cysteine. In: Liebigs Annalen der Chemie 1982, pp. 1995–1998. doi : 10.1002 / jlac.198219821108 .