65002-17-7 Usage
Description
Bucillamine is an orally active immunomodulator with potent inhibitory effects on collagenase activity and rheumatoid factor inactivation, making it a promising therapeutic agent for the treatment of rheumatoid arthritis. Its efficacy in improving erythrocyte sedimentation, grip power, joint swelling, and duration of morning stiffness significantly surpasses that of penicillamine.
Uses
Used in Pharmaceutical Industry:
Bucillamine is used as an antirheumatic agent for the treatment of rheumatoid arthritis. Its immunomodulatory properties and ability to inhibit collagenase activity and inactivate rheumatoid factor contribute to its effectiveness in managing the symptoms and progression of the disease.
Originator
Santen (Japan)
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).
Therapeutic Function
Antirheumatic, Immunomodulator
Check Digit Verification of cas no
The CAS Registry Mumber 65002-17-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,5,0,0 and 2 respectively; the second part has 2 digits, 1 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 65002-17:
(7*6)+(6*5)+(5*0)+(4*0)+(3*2)+(2*1)+(1*7)=87
87 % 10 = 7
So 65002-17-7 is a valid CAS Registry Number.
InChI:InChI=1/C7H13NO3S2/c1-7(2,13)6(11)8-4(3-12)5(9)10/h4,12-13H,3H2,1-2H3,(H,8,11)(H,9,10)/t4-/m0/s1
