Carbocisteine

Carbocisteine
Names
	IUPAC name (R)-2-Amino-3-(carboxymethylsulfanyl)propanoic acid
	Other names S-Carboxymethyl-L-cysteine; Actithiol, Lisomucil, Muciclar, Mucodyne, Mucolex, Rhinathiol, Transbronchin[1]
Identifiers
CAS Number	638-23-3 (R) ; 2387-59-9 (RS) ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:16163 ;
ChEMBL	ChEMBL396416 ;
ChemSpider	168055 ;
DrugBank	DB04339 ;
ECHA InfoCard	100.010.298
KEGG	D06393 ;
PubChem CID	193653;
UNII	740J2QX53R ;
CompTox Dashboard (EPA)	DTXSID30110060 ;
	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, 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.[2][3] 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.[4] Carbocisteine is produced by alkylation of cysteine with chloroacetic acid.[5]

References

Carbocisteine. drugbank.ca
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.; Shi, Y.; Liu, C. T.; Chen, P.; Li, Q.; Wang, Z. S.; Huang, Y. J.; Luo, Z. Y.; Chen, F. P.; Yuan, J. Z.; Yuan, B. T.; Qian, H. P.; Zhi, R. C.; Zhong, N. S. (2008). "Effect of carbocisteine on acute exacerbation of chronic obstructive pulmonary disease (PEACE Study): A randomised placebo-controlled study". Lancet. 371 (9629): 2013–8. doi:10.1016/S0140-6736(08)60869-7. PMID 18555912.
Yasuda, H.; Yamaya, M.; Sasaki, T.; Inoue, D.; Nakayama, K.; Tomita, N.; Yoshida, M.; 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): 378–80. doi:10.1111/j.1532-5415.2005.00592_9.x. PMID 16460403.
Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 544. ISBN 9783527607495.
Karlheinz Drauz; Ian Grayson; Axel Kleemann; Hans‐Peter Krimmer; Wolfgang Leuchtenberger; Christoph Weckbecker (2007). "Amino Acids". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_057.pub2.CS1 maint: uses authors parameter (link)

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[1] Carbocisteine. drugbank.ca

[2] 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.; Shi, Y.; Liu, C. T.; Chen, P.; Li, Q.; Wang, Z. S.; Huang, Y. J.; Luo, Z. Y.; Chen, F. P.; Yuan, J. Z.; Yuan, B. T.; Qian, H. P.; Zhi, R. C.; Zhong, N. S. (2008). "Effect of carbocisteine on acute exacerbation of chronic obstructive pulmonary disease (PEACE Study): A randomised placebo-controlled study". Lancet. 371 (9629): 2013–8. doi:10.1016/S0140-6736(08)60869-7. PMID 18555912.

[3] Yasuda, H.; Yamaya, M.; Sasaki, T.; Inoue, D.; Nakayama, K.; Tomita, N.; Yoshida, M.; 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): 378–80. doi:10.1111/j.1532-5415.2005.00592_9.x. PMID 16460403.

[Fis2006-4] Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 544. ISBN 9783527607495.

[5] Karlheinz Drauz; Ian Grayson; Axel Kleemann; Hans‐Peter Krimmer; Wolfgang Leuchtenberger; Christoph Weckbecker (2007). "Amino Acids". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_057.pub2.CS1 maint: uses authors parameter (link)