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Bucillamine

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Bucillamine
Skeletal formula of bucillamine
Ball-and-stick model of the bucillamine molecule
Names
IUPAC name
2-[(2-Methyl-2-sulfanylpropanoyl)amino]-3-sulfanylpropanoic acid[citation needed]
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
KEGG
MeSH bucillamine
UNII
  • InChI=1S/C7H13NO3S2/c1-7(2,13)6(11)8-4(3-12)5(9)10/h4,12-13H,3H2,1-2H3,(H,8,11)(H,9,10) checkY
    Key: VUAFHZCUKUDDBC-UHFFFAOYSA-N checkY
  • CC(C)(S)C(=O)NC(CS)C(=O)O
Properties
C7H13NO3S2
Molar mass 223.31 g·mol−1
log P 1.032
Acidity (pKa) 3.012
Basicity (pKb) 10.985
Pharmacology
M01CC02 (WHO)
Related compounds
Related Alkanoic acids
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Bucillamine is an antirheumatic agent developed from tiopronin. It is mainly used in Japan and Korea. Activity is mediated by the two thiol groups that the molecule contains. Research done in USA showed positive transplant preservation properties.[1]

References

  1. ^ Amersi, F.; Nelson, S. K.; Shen, X. D.; Kato, H.; Melinek, J.; Kupiec-Weglinski, J. W.; Horwitz, L. D.; Busuttil, R. W.; Horwitz, M. A. (2002). "Bucillamine, a Thiol Antioxidant, Prevents Transplantation-Associated Reperfusion Injury" (pdf). Proceedings of the National Academy of Sciences. 99 (13): 8915–8920. doi:10.1073/pnas.132026099. PMC 124398. PMID 12084933.
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