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Cysteine methyl ester

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(Redirected from Mecysteine) Chemical compound Pharmaceutical compound
Cysteine methyl ester
Clinical data
Other namesMethyl L-cysteinate
AHFS/Drugs.comInternational Drug Names
Identifiers
IUPAC name
  • methyl (2R)-2-amino-3-sulfanylpropanoate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.017.842 Edit this at Wikidata
Chemical and physical data
FormulaC4H9NO2S
Molar mass135.18 g·mol
3D model (JSmol)
SMILES
  • COC(=O)C(CS)N
InChI
  • InChI=1S/C4H9NO2S/c1-7-4(6)3(5)2-8/h3,8H,2,5H2,1H3/t3-/m0/s1
  • Key:MCYHPZGUONZRGO-VKHMYHEASA-N

Cysteine methyl ester is the organic compound with the formula HSCH2CH(NH2)CO2CH3. It is a white solid substance, known as the methyl ester of the amino acid, cysteine.

Uses

Under the brand name Mecysteine, cysteine methyl ester is a commercial drug for mucolytic activity. The compound has an ability to break down or lower the viscosity of mucin-containing secretions or components of fluids by chronic and acute respiratory disorders. The drug is sold under the commercial names Delta in Paraguay, and Pectite and Zeotin in Japan.

Cysteine methyl ester is also used as a building block for synthesis of N,S-heterocycles.

References

  1. Page CP (2018). "Respiratory System: Mucolytics". In Datta ST, Xiu P (eds.). Pharmacology (Fifth ed.). Philadelphia, PA: Elsevier. p. 40. ISBN 978-0-7020-7345-8.
  2. "Mecysteine". Drugs.com.
  3. Tanaka T, Nakashima T, Ueda T, Tomii K, Kouno I (June 2007). "Facile discrimination of aldose enantiomers by reversed-phase HPLC". Chemical & Pharmaceutical Bulletin. 55 (6): 899–901. doi:10.1248/cpb.55.899. hdl:10069/14910. PMID 17541189.
  4. Hamada Y, Shibata M, Sugiura T, Kato S, Shioiri T (1987). "New methods and reagents in organic synthesis. 67. A general synthesis of derivatives of optically pure 2-(1-aminoalkyl)thiazole-4-carboxylic acids". The Journal of Organic Chemistry. 52 (7): 1252–1255. doi:10.1021/jo00383a014.
Cough and cold preparations (R05)
Expectorants
Mucolytics
Cough suppressants
Opium alkaloids,
opioids,
and derivatives
Other
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