1460. Bucillamine

Nomenclature

CAS number: 65002-17-7
N-(2-Mercapto-2-methyl-1-oxopropyl)-l-cysteine; N-(2-mercapto-2-methylpropanoyl)-l-cysteine; N-(2-mercaptoisobutyryl)-l-cysteine; tiobutarit; thiobutarit; DE-019; SA-96; Rimatil (Santen).
C7H13NO3S2; mol wt 223.31.
C 37.65%, H 5.87%, N 6.27%, O 21.49%, S 28.72%.

Description and 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).

Chemical structure

Properties

Crystals from ethyl acetate, mp 139-140°. [α]D25 +32.3° (c = 1.0 in ethanol). LD50 in mice (mg/kg): 2285 i.p.; 989.6 i.v. (Fujita, 1981).

Therapeutic Category

Antirheumatic.

Keywords

Antiarthritic/Antirheumatic; Immunomodulator