Bucillamine

Title: Bucillamine
CAS Registry Number: 65002-17-7
CAS Name: N-(2-Mercapto-2-methyl-1-oxopropyl)-L-cysteine
Additional Names: N-(2-mercapto-2-methylpropanoyl)-L-cysteine; N-(2-mercaptoisobutyryl)-L-cysteine; tiobutarit; thiobutarit
Manufacturers' Codes: DE-019; SA-96
Trademarks: Rimatil (Santen)
Molecular Formula: C7H13NO3S2
Molecular Weight: 223.31
Percent Composition: C 37.65%, H 5.87%, N 6.27%, O 21.49%, S 28.72%
Literature References: Disease modifying antirheumatic drug (DMARD) which modulates the immune response; structurally related to tiopronin, q.v. Prepn: T. Fujita et al., DE 2709820; eidem, US 4305958 (1977, 1981 both to Santen); M. Oya et al., Chem. Pharm. Bull. 29, 940 (1981). GC-MS determn in blood: K. Matsuura et al., J. Mass Spectrom. Soc. Jpn. 46, 25 (1998). Clinical immunopharmacology: H. Matsuno et al., Drugs Exp. Clin. Res. 19, 205 (1993). Clinical trials in rheumatoid arthritis: M. Yasuda et al., Clin. Rheumatol. 13, 446 (1994); H. A. Kim, Y. W. Song, Rheumatol. Int. 17, 5 (1997).
Properties: Crystals from ethyl acetate, mp 139-140°. [a]D25 +32.3° (c = 1.0 in ethanol). LD50 in mice (mg/kg): 2285 i.p.; 989.6 i.v. (Fujita, 1981).
Melting point: mp 139-140°
Optical Rotation: [a]D25 +32.3° (c = 1.0 in ethanol)
Toxicity data: LD50 in mice (mg/kg): 2285 i.p.; 989.6 i.v. (Fujita, 1981)
Therap-Cat: Antirheumatic.
Keywords: Antiarthritic/Antirheumatic; Immunomodulator.
Bucindolol Buclizine Buclosamide Bucloxic Acid Bucolome

Bucillamine
Skeletal formula of bucillamine
Identifiers
CAS number 65002-17-7 R YesY
PubChem 2459, 656604 R, 636373 S
ChemSpider 2365 YesY
UNII R80LRA5WTF YesY
KEGG D01809 YesY
MeSH bucillamine
ChEMBL CHEMBL80830 YesY
ATC code M01CC02
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C7H13NO3S2
Molar mass 223.31 g mol−1
log P 1.032
Acidity (pKa) 3.012
Basicity (pKb) 10.985
Related compounds
Related alkanoic acids
  • Acetylcysteine
  • Glycylglycine
  • Iminodiacetic acid
  • Nitrilotriacetic acid
  • N-Oxalylglycine
  • Tiopronin
  • Oxalyldiaminopropionic acid
  • gamma-Glutamylcysteine
Related compounds
  • N-Acetylglycinamide
Except where noted otherwise, 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]