Bucillamine

Bucillamine
Names


IUPAC name 2-[(2-Methyl-2-sulfanylpropanoyl)amino]-3-sulfanylpropanoic acid
Identifiers
CAS Number	65002-17-7 R^Y
ChEMBL	ChEMBL80830^Y
ChemSpider	2365^Y
Jmol interactive 3D	Image Image
KEGG	D01809^Y
MeSH	bucillamine
PubChem	2459 656604 R 636373 S
UNII	R80LRA5WTF^Y
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)^Y Key: VUAFHZCUKUDDBC-UHFFFAOYSA-N^Y
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 (pK_a)	3.012
Basicity (pK_b)	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

↑ 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.

Specific antirheumatic products / DMARDs (M01C)

Quinolines	Oxycinchophen

Gold preparations	Sodium aurothiomalate Sodium aurothiosulfate Auranofin Aurothioglucose Aurotioprol

Other	Penicillamine #/Bucillamine Chloroquine #/Hydroxychloroquine Leflunomide Sulfasalazine # antifolate (Methotrexate #) thiopurine (Azathioprine) #

^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

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