BUCILLAMINE Chemical Properties

Melting point:

119-123°C

alpha 

D25 +32.3° (c = 1.0 in ethanol)

Boiling point:

438.0±45.0 °C(Predicted)

Density 

1.3934 (rough estimate)

refractive index 

1.6370 (estimate)

storage temp. 

Hygroscopic, -20°C Freezer, Under Inert Atmosphere

solubility 

DMSO (Very Slightly), Ethanol (Slightly), Methanol (Slightly), Water (Slightly)

pka

3.01±0.10(Predicted)

form 

Solid

color 

White to Pale Yellow

Stability:

Air Sensitive, Hygroscopic, Unstable in Solution

CAS DataBase Reference

65002-17-7(CAS DataBase Reference)

Safety Information

Toxicity

LD50 in mice (mg/kg): 2285 i.p.; 989.6 i.v. (Fujita, 1981)

BUCILLAMINE Usage And Synthesis

Description

Bucillamine is an orally active immunomodulator useful in the treatment of rheumatoid arthritis. Its potencies in inhibiting collagenase activity and inactivating rheumatoid factor far exceed those of penicillamine. In man, bucillamine reportedly brings about significant improvements over placebo in erythrocyte sedimentation, grip power, joint swelling and duration of morning stiffness.

Chemical Properties

Off-White Solid

Originator

Santen (Japan)

Uses

An antirheumatic agent.

Definition

ChEBI: Bucillamine is an organic molecular entity.

Manufacturing Process

Preparation of N-(2-benzylmercaptoisobutyryl)-S-benzyl-L-cysteine:
1). 73.9 g of S-benzyl-L-cysteine were dissolved in 700 ml of 1 N sodium hydroxide solution. The solution was cooled in an ice bath and stirred. 2- Benzylmercaptoisobutyryl chloride, which was obtained by reacting 63.1 g of 2-benzylmercaptoisobutyric acid with 39.3 g of thionyl chloride, was added dropwise to this solution. The resulting mixture was then stirred for one hour, acidified with hydrochloric acid and extracted with ethyl acetate. The extract was washed with water, dried over sodium sulfate and evaporated to dryness.
The residue was chromatographed on silica gel with benzene/ethylacetate (1:1) as an eluant. The eluate was evaporated to dryness and an oily residue weighing 46.9 g, representing a yield of 74%, was obtained. 2). The obtained in (1) above were dissolved in 500 ml of liquid ammonia and 21.1 g of metallic sodium were added slowly with stirring. After completion of reaction, 59.4 g of ammonium chloride were added and thereafter the ammonia was removed by distillation. Water was added to the residue to dissolve the solid. The resulting water layer was separated, washed with ethyl acetate, and acidified with hydrochloric acid under cooling. The precipitates thus obtained were extracted with ethyl acetate. The extract was washed with water, dried over sodium sulfate and evaporated to dryness. The product weighed 43.6 g, representing a yield of 88%. After recrystallization from ethyl acetate, the desired compound, melting at 139°-140°C, was obtained. [α]D 25=+32.3° (c=1.0, ethanol).

brand name

Rimatil

Therapeutic Function

Antirheumatic, Immunomodulator

BUCILLAMINE(65002-17-7)Related Product Information

• I-BUT-CYS-OH
• BUCILLAMINE
• Tiopronin