BUCILLAMINE

BUCILLAMINE Basic information
Product Name:BUCILLAMINE
Synonyms:sa96;thiobutarit;BUCILLAMINE;(R)-3-Mercapto-2-(2-Mercapto-2-MethylpropanaMido)propanoic acid;de-019;L-Cysteine, N-(2-mercapto-2-methyl-1-oxopropyl)-;N-(2-Mercaptoisobutyryl)cysteine;Tiobutarit
CAS:65002-17-7
MF:C7H13NO3S2
MW:223.31
EINECS:
Product Categories:Amino Acids & Derivatives;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
Mol File:65002-17-7.mol
BUCILLAMINE Structure
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)
pka3.01±0.10(Predicted)
form Solid
color White to Pale Yellow
Stability:Air Sensitive, Hygroscopic, Unstable in Solution
CAS DataBase Reference65002-17-7(CAS DataBase Reference)
Safety Information
ToxicityLD50 in mice (mg/kg): 2285 i.p.; 989.6 i.v. (Fujita, 1981)
MSDS Information
BUCILLAMINE Usage And Synthesis
DescriptionBucillamine 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 PropertiesOff-White Solid
OriginatorSanten (Japan)
UsesAn antirheumatic agent.
DefinitionChEBI: Bucillamine is an organic molecular entity.
Manufacturing ProcessPreparation 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 nameRimatil
Therapeutic FunctionAntirheumatic, Immunomodulator
Tiopronin I-BUT-CYS-OH BUCILLAMINE

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