Bucillamine

Bucillamine

Names
IUPAC name 2-[(2-Methyl-2-sulfanylpropanoyl)amino]-3-sulfanylpropanoic acid
Identifiers
CAS Number	65002-17-7 R
ChEMBL	ChEMBL80830
ChemSpider	2365
Jmol interactive 3D	Image Image
KEGG	D01809
MeSH	bucillamine
PubChem	2459 656604 R 636373 S
UNII	R80LRA5WTF
InChI 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) Key: VUAFHZCUKUDDBC-UHFFFAOYSA-N
SMILES CC(C)(S)c(:[o]):[nH]C(CS)c(:[o]):[oH] CC(C)(S)C(=O)NC(CS)C(O)=O
Properties
Chemical formula	C7H13NO3S2
Molar mass	223.31 g·mol^−1
log P	1.032
Acidity (pKa)	3.012
Basicity (pKb)	10.985
Pharmacology
ATC code	M01CC02
Related compounds
Related alkanoic acids	Acetylcysteine Glycylglycine Iminodiacetic acid Nitrilotriacetic acid N-Oxalylglycine Tiopronin Oxalyldiaminopropionic acid gamma-Glutamylcysteine
Related compounds	N-Acetylglycinamide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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.