Bucillamine

Base Information

• Chemical Name: Bucillamine
• CAS No.: 65002-17-7
• Molecular Formula: C7H13NO3S2
• Molecular Weight: 223.317
• Hs Code.: 2930909090
• UNII: R80LRA5WTF
• DSSTox Substance ID: DTXSID2048587
• Nikkaji Number: J22.800A
• Wikipedia: Bucillamine
• Wikidata: Q4982752
• NCI Thesaurus Code: C83561
• Metabolomics Workbench ID: 153200
• ChEMBL ID: CHEMBL80830
• Mol file: 65002-17-7.mol

Synonyms:2-mercapto-2-methylpropanoyl-L-cysteine;bucillamine;DE-019;DE019;L-cysteine, N-(2-mercapto-2-methyl-1-oxopropyl)-;N-(2-mercapto-2-methylpropionyl)-L-cysteine;Rimatil;SA 96;SA-96;tiobutarit

Chemical Property of Bucillamine

Chemical Property:

• Vapor Pressure: 6.77E-09mmHg at 25°C
• Melting Point: 119-123oC
• Refractive Index: 1.552
• Boiling Point: 438 °C at 760 mmHg
• PKA: 3.01±0.10(Predicted)
• Flash Point: 218.7 °C
• PSA: 144.00000
• Density: 1.289 g/cm³
• LogP: 0.58490
• Storage Temp.: Hygroscopic, -20?C Freezer, Under Inert Atmosphere
• Solubility.: DMSO (Very Slightly), Ethanol (Slightly), Methanol (Slightly), Water (Slightly)
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 223.03368562
• Heavy Atom Count: 13
• Complexity: 218

Purity/Quality:

99.5% ^*data from raw suppliers

Bucillamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N,Xi
• Hazard Codes: T,N,Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C(=O)NC(CS)C(=O)O)S
• Isomeric SMILES: CC(C)(C(=O)N[C@@H](CS)C(=O)O)S
• Recent ClinicalTrials: Bucillamine in Treatment of Patients With COVID-19
• Recent NIPH Clinical Trials: Open-label, multicenter, randomized controlled trials, for comparing remission induction rate of a dose-escalation therapy of methotrexate and an additional combination therapy with bucillamine for naive patients to over 8 mg/weekly of methotrexate.
• 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.
• Uses: An antirheumatic agent.
• Therapeutic Function: Antirheumatic, Immunomodulator

Technology Process of Bucillamine

There total 3 articles about Bucillamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 81.0%

S-benzyl-N-(S-benzyl-2-mercapto-2-methylpropanoyl)-L-cysteine (65002-16-6) → bucillamine (65002-17-7)

Guidance literature:

With ammonia; sodium;

DOI:10.1248/cpb.29.940

Reference yield:

L-Cysteine (52-90-4) + 2-mercapto-2-methylpropanoic acid (4695-31-2) → bucillamine (65002-17-7)

Guidance literature:

With potassium carbonate; dicyclohexyl-carbodiimide; Yield given. Multistep reaction; 1.) EtOAc, r.t., 1 h; 2.) EtOAc, MeOH, water, r.t., 4 h;

DOI:10.1248/cpb.29.940

Reference yield:

→ bucillamine (65002-17-7)

Guidance literature:

upstream raw materials:

S-benzyl-N-(S-benzyl-2-mercapto-2-methylpropanoyl)-L-cysteine

L-Cysteine

2-mercapto-2-methylpropanoic acid

Downstream raw materials:

(4R)-tetrahydro-7,7-dimethyl-6-oxo-3H-1,2,5-dithiazepine-4-carboxylic acid

2-methylmercapto-isobutyroyl-l-S-methylcysteine

Refernces

• 1、 -. "Cysteine derivatives". . . Retrieved 2008/06/13.