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

Cysteine methyl ester is the organic compound with the formula HSCH2CH(NH2)CO2CH3. A white solid, it is the methyl ester of the amino acid cysteine.

Uses

Under the brand name Mecysteine, cysteine methyl ester is a commercial drug with mucolytic activity.[1] It is used as mucolytic and fluidifying for chronic and acute respiratory disorders. The drug is sold under the commercial names Delta in Paraguay, and Pectite and Zeotin in Japan.[2]

Cysteine methyl ester is also used as a building block for synthesis of N,S-heterocycles.[3][4]

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.
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