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{{drugbox
{{chembox
| IUPAC_name        = 2-amino-3-(carboxymethylsulfanyl)propanoic acid
| Watchedfields = changed
| image            = carbocisteine.png
| UNII_Ref = {{fdacite|correct|FDA}}
| CAS_number        =  
| UNII = 740J2QX53R
| ATC_prefix        = R05
| verifiedrevid = 443673182
| ATC_suffix        = CB03
| ImageFile =Carboxymethylcystein Formulae.png
| PubChem          = 1080
| ImageSize = 200px
| DrugBank          =  
| ImageFile1 =Carbocisteine 3D.png
| C=5|H=9|N=1|O=4|S=1
| ImageSize1 = 200px
| molecular_weight  = 179.195 g/mol
| IUPACName = (''R'')-2-Amino-3-(carboxymethylsulfanyl)propanoic acid
| bioavailability  =  
| OtherNames = ''S''-Carboxymethyl-<small>L</small>-cysteine; Mucodyne, Solmux, Rhinathiol, Humex, Lisomucil, Fluditec, Exputex, Mucolit, Reodyn, Carbotoux, Flemex, Carbolin, Muflex
| protein_bound    =  
|Section1={{Chembox Identifiers
| metabolism        =  
| KEGG_Ref = {{keggcite|correct|kegg}}
| elimination_half-life =  
| KEGG = D06393
| excretion        =  
| InChI1 = 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
| pregnancy_AU      = <!-- A / B1 / B2 / B3 / C / D / X -->
| InChIKey1 = GBFLZEXEOZUWRN-VKHMYHEABX
| pregnancy_US      = <!-- A / B            / C / D / X -->
| SMILES1 = O=C(O)[C@@H](N)CSCC(=O)O
| pregnancy_category=
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| legal_AU          = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| StdInChI = 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
| legal_CA          =  <!--             / Schedule I, II, III, IV, V, VI, VII, VIII -->
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| legal_UK          = <!-- GSL        / P      / POM / CD / Class A, B, C -->
| StdInChIKey = GBFLZEXEOZUWRN-VKHMYHEASA-N
| legal_US          = <!-- OTC                  / Rx-only  / Schedule I, II, III, IV, V -->
| CASNo_Ref = {{cascite|correct|??}}
| legal_status      =  
| CASNo =638-23-3
| routes_of_administration =  
| CASNo_Comment = (''R'')
| CASNo1 = 2387-59-9
| CASNo1_Comment = (''RS'')
| PubChem = 193653
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 396416
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 168055
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 16163
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB04339
| SMILES =O=C(O)C(N)CSCC(=O)O
| InChI = 1/C5H9NO4S/c6-3(5(9)10)1-11-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)
| InChIKey = GBFLZEXEOZUWRN-UHFFFAOYAN
| ATCvet =
| ATCCode_prefix = R05
| ATCCode_suffix = CB03
| ATC_Supplemental =
  }}
|Section2={{Chembox Properties
| C =5|H=9|N=1|O=4|S=1
| Appearance =Colorless solid
| Density =
| MeltingPtC = 204 to 207
| Melting_notes =
| BoilingPtC =
| Solubility =
  }}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
  }}
|Section5={{Chembox Pharmacology
| AdminRoutes =
| Bioavail =
| Metabolism =
| HalfLife =
| ProteinBound =
| Excretion =
| Legal_status =
| Legal_US =
| Legal_UK =
| Legal_AU =
| Legal_CA =
| PregCat =  
| PregCat_AU =  
| PregCat_US =  
}}
}}
}}
'''Carbocisteine''' is a [[mucolytic]] that 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.


{{pharmacology-stub}}
'''Carbocisteine''' 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 [[antitussive]]s (cough suppressants) or medicines that dry up bronchial secretions.


Carbocisteine is produced by [[alkylation]] of [[cysteine]] with [[chloroacetic acid]].<ref>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}}</ref>
==Trade names==
*Fluidol, Humotusin: Romania
*Rhinathiol: Bulgaria, Congo, Hong Kong, Hungary, Latvia, Lithuania, Malaysia, Oman, Romania, Singapore, South Korea, Switzerland, Taiwan, Thailand, Tunisia, and Vietnam<ref>http://www.drugs.com/international/rhinathiol.html</ref>
*Mucodyne: United Kingdom, India, Ireland, Japan, Netherlands, Serbia.
*Mucoral: Portugal
*Mucosol: Egypt
*Solmux, Loviscol: Philippines
==References==
<references/>


{{Cough and cold preparations}}
{{Cough and cold preparations}}


[[Category:Antitussives]]
[[Category:Dicarboxylic acids]]
[[Category:Amino acids]]
[[Category:Expectorants]]
[[Category:Thioethers]]
[[Category:Thioethers]]
[[Category:Amino acid derivatives]]

Revision as of 16:04, 8 April 2015

Template:Chembox E numberTemplate:Chembox AppearanceTemplate:Chembox MeltingPtTemplate:Chembox Pharmacology
Carbocisteine
File:Carboxymethylcystein Formulae.png
File:Carbocisteine 3D.png
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value).
KEGG
Properties
C5H9NO4S
Molar mass 179.19 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☑Y verify (what is ☑Y☒N ?)
Infobox references

Carbocisteine 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.

Carbocisteine is produced by alkylation of cysteine with chloroacetic acid.[1]

Trade names

  • Fluidol, Humotusin: Romania
  • Rhinathiol: Bulgaria, Congo, Hong Kong, Hungary, Latvia, Lithuania, Malaysia, Oman, Romania, Singapore, South Korea, Switzerland, Taiwan, Thailand, Tunisia, and Vietnam[2]
  • Mucodyne: United Kingdom, India, Ireland, Japan, Netherlands, Serbia.
  • Mucoral: Portugal
  • Mucosol: Egypt
  • Solmux, Loviscol: Philippines

References

  1. ↑ 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
  2. ↑ http://www.drugs.com/international/rhinathiol.html

Template:Cough and cold preparations

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