Introduction：Basic information about BUCILLAMINE CAS 65002-17-7, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
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 |
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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 rheumatoidarthritis. Its potencies in inhibiting collagenase activity and inactivating rheumatoid factorfar exceed those of penicillamine. In man, bucillamine reportedly brings about significantimprovements over placebo in erythrocyte sedimentation, grip power, joint swelling andduration 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 sodiumhydroxide solution. The solution was cooled in an ice bath and stirred. 2-Benzylmercaptoisobutyryl chloride, which was obtained by reacting 63.1 g of2-benzylmercaptoisobutyric acid with 39.3 g of thionyl chloride, was addeddropwise to this solution. The resulting mixture was then stirred for one hour,acidified with hydrochloric acid and extracted with ethyl acetate. The extractwas 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 and21.1 g of metallic sodium were added slowly with stirring. After completion ofreaction, 59.4 g of ammonium chloride were added and thereafter theammonia was removed by distillation. Water was added to the residue todissolve the solid. The resulting water layer was separated, washed with ethylacetate, and acidified with hydrochloric acid under cooling. The precipitatesthus obtained were extracted with ethyl acetate. The extract was washed withwater, dried over sodium sulfate and evaporated to dryness. The productweighed 43.6 g, representing a yield of 88%. After recrystallization from ethylacetate, the desired compound, melting at 139°-140°C, was obtained.[α]D25=+32.3° (c=1.0, ethanol). |
| Brand name | Rimatil |
| Therapeutic Function | Antirheumatic, Immunomodulator |
BUCILLAMINE Preparation Products And Raw materials
| Raw materials | Thionyl chloride-->Ammonia-->Ammonium chloride-->Silica gel-->Ethyl phenylacetate-->Isobutyryl chloride-->2-MERCAPTOISOBUTYRIC ACID-->S-Benzyl-L-cysteine-->Sodium |
