Belinostat

Base Information

• Chemical Name: Belinostat
• CAS No.: 414864-00-9
• Molecular Formula: C15H14N2O4S
• Molecular Weight: 318.353
• Hs Code.: 29350090
• NSC Number: 726630
• UNII: F4H96P17NZ
• DSSTox Substance ID: DTXSID60194378
• Nikkaji Number: J2.221.253B,J2.920.351B
• Wikipedia: Belinostat
• Wikidata: Q4882925
• NCI Thesaurus Code: C48812
• RXCUI: 1543543
• Pharos Ligand ID: AA7F8LN8G27V,AA7R9D1PBQ86
• Metabolomics Workbench ID: 61442
• ChEMBL ID: CHEMBL408513
• Mol file: 414864-00-9.mol

Synonyms:Belecodaq;belinostat;PXD101

Chemical Property of Belinostat

Chemical Property:

• Refractive Index: 1.667
• PKA: 8.31±0.10(Predicted)
• PSA: 103.88000
• Density: 1.428 g/cm³
• LogP: 3.55070
• Storage Temp.: Amber Vial, Refrigerator, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 318.06742811
• Heavy Atom Count: 22
• Complexity: 492

Purity/Quality:

Belinostat(PXD-101) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antineoplastic Agents
• Canonical SMILES: C1=CC=C(C=C1)NS(=O)(=O)C2=CC=CC(=C2)C=CC(=O)NO
• Isomeric SMILES: C1=CC=C(C=C1)NS(=O)(=O)C2=CC=CC(=C2)/C=C/C(=O)NO
• Recent ClinicalTrials: Tremelimumab, Durvalumab, and Belinostat for the Treatment of ARID1A Mutated Metastatic or Unresectable, Locally Advanced Urothelial Carcinoma
• Recent EU Clinical Trials: Randomised Open Label Adaptive Phase III trial of addition of Belinostat to chemotherapy in patients with locally advanced potentially resectable Thymic Epithelial Tumors (TET)
• Description: Belinostat is a drug which was developed by Spectrum Pharmaceuticals and is currently marketed by Onxeo as Beleodaq?. The drug, which received fast track designation by the United States Food and Drug Administration (US FDA) and was approved for the treatment of hematological malignancies and solid tumors associated with peripheral T-cell lymphoma (PTCL) in 2014, is a histone deacetylase (HDAC) inhibitor and is the third such treatment to receive accelerated approval for PTCL, the others being vorinostat (Zolinza?) and pralatrexate (Folotyn?). Although belinostat was not yet approved in Europe as of August 2014, the compound exhibits a safety profile considered to be acceptable for HDAC inhibitors–less than 25% of patients reported adverse effects and these most frequently were nausea, fatigue, pyrexia, anemia, and emesis.
• Uses: Belinostat is a novel histone deacetylase 3 selective inhibitor, which protects the β cells from cytokine-induced apoptosis.

Technology Process of Belinostat

There total 11 articles about Belinostat 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: 93.6%

C17H17NO4S → N-hydroxy-3-(3-phenylaminosulfonylphenyl)acrylamide (414864-00-9)

Guidance literature:

With hydroxylamine hydrochloride; sodium hydroxide; In water; at -5 ℃; for 6h; Temperature;

Reference yield: 92.5%

C16H15NO4S (412268-99-6) → N-hydroxy-3-(3-phenylaminosulfonylphenyl)acrylamide (414864-00-9)

Guidance literature:

With hydroxylamine hydrochloride; sodium hydroxide; In water; at 10 ℃; for 2h;

Reference yield: 83.2%

C15H13NO4S (412269-00-2) → N-hydroxy-3-(3-phenylaminosulfonylphenyl)acrylamide (414864-00-9)

Guidance literature:

C₁₅H₁₃NO₄S; With oxalyl dichloride; In tetrahydrofuran; at 25 - 35 ℃; for 0.5h; Large scale;

With hydroxylamine hydrochloride; potassium carbonate; In tetrahydrofuran; water; at 0 - 10 ℃; for 0.166667h; Autoclave; Large scale;

upstream raw materials:

3-formyl-N-phenylbenzene-1-sulfonamide

C₁₅H₁₃NO₄S

3-(hydroxymethyl)-N-phenylbenzenesulfonamide

m-sulfobenzoic acid, monosodium salt

Downstream raw materials:

belinostat

Refernces

• 1、 -. "Method for preparing belinostat". Paragraph 0041; 0044; 0048; 0049; 0053; 0054; 0058-0096. . Retrieved 2019/02/26.
• 2、 -. "A he belli department is suitable for industrial production of synthetic method". Paragraph 0011; 0040; 0041; 0042. . Retrieved 2016/10/08.