Carbocisteine

Carbocisteine

Names
IUPAC name (R)-2-Amino-3-(carboxymethylsulfanyl)propanoic acid
Other names S-Carboxymethyl-L-cysteine; Mucodyne, Solmux, Rhinathiol, Humex, Lisomucil, Fluditec, Exputex, Mucolit, Reodyn, Carbotoux, Flemex, Carbolin, Muflex
Identifiers
CAS Number	638-23-3 (R) 2387-59-9 (RS)
3D model (Jmol)	Interactive image Interactive image
ChEBI	CHEBI:16163
ChEMBL	ChEMBL396416
ChemSpider	168055
DrugBank	DB04339
ECHA InfoCard	100.010.298
KEGG	D06393
PubChem	193653
UNII	740J2QX53R
InChI 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 Key: GBFLZEXEOZUWRN-VKHMYHEASA-N 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
SMILES O=C(O)C(N)CSCC(=O)O O=C(O)[C@@H](N)CSCC(=O)O
Properties
Chemical formula	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
ATC code	R05CB03 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Carbocisteine (INN), also called carbocysteine (USAN), 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.^[1][2] Carbocisteine should not be used with antitussives (cough suppressants) or medicines that dry up bronchial secretions.

Carbocisteine is produced by alkylation of cysteine with chloroacetic acid.^[3]

Trade names

• Bronles: Macedonia^[4]
• Flemex: Vietnam
• Fluifort: Italy
• Carbex: Pakistan
• Mucospect: South Africa
• Exputex: Ireland
• Fluidol, Humotusin: Romania
• Rhinathiol: Bulgaria, Congo, Hong Kong, Hungary, Latvia, Lithuania, Malaysia, Oman, Romania, Singapore, South Korea, Switzerland, Taiwan, Thailand, Tunisia, and Vietnam^[5]
• Mucodyne: United Kingdom, India, Ireland, Japan, Netherlands, Serbia.
• Mucoral: Portugal
• Mucosol: Egypt
• Solmux, Loviscol: Philippines
• Mucolit: Israel

References

1. Zheng, J.P., Kang, J., Huang, S.G., Chen, P., Yao, W.Z., Yang, L., Bai, C.X., Wang, C.Z., Wang, C., Chen, B.Y. and Shi, Y. (2008)."Effect of carbocisteine on acute exacerbation of chronic obstructive pulmonary disease (PEACE Study): a randomised placebo-controlled study. The Lancet, 371(9629), 2013-2018.
2. Yasuda, H., Yamaya, M., Sasaki, T., Inoue, D., Nakayama, K., Tomita, N., Yoshida, M. and Sasaki, H., 2006. Carbocisteine reduces frequency of common colds and exacerbations in patients with chronic obstructive pulmonary disease. Journal of the American Geriatrics Society, 54(2), pp.378-380.
3. Karlheinz Drauz, Ian Grayson, Axel Kleemann, Hans-Peter Krimmer, Wolfgang Leuchtenberger, Christoph Weckbecker “Amino Acids” in Ullmann's Encyclopedia of Industrial Chemistry, 2007, Wiley-VCH, Weinheim. doi:10.1002/14356007.a02_057.pub2
4. "Bronles". alkaloid.com.mk.
5. "Rhinathiol". Drugs.com.