Roxadustat

Base Information

• Chemical Name: Roxadustat
• CAS No.: 808118-40-3
• Deprecated CAS: 1019198-38-9
• Molecular Formula: C₁₉H₁₆N₂O₅
• Molecular Weight: 352.346
• European Community (EC) Number: 813-400-2
• UNII: X3O30D9YMX
• ChEMBL ID: CHEMBL2338329
• DSSTox Substance ID: DTXSID60230644
• Metabolomics Workbench ID: 149278
• NCI Thesaurus Code: C141436
• Nikkaji Number: J3.176.363K
• Pharos Ligand ID: DF2VY1XDT8YN
• Wikidata: Q27088611
• Wikipedia: Roxadustat
• Mol file: 808118-40-3.mol

Synonyms:FG-4592;FG4592;roxadustat

Chemical Property of Roxadustat

Chemical Property:

• Boiling Point: 684.3 °C at 760 mmHg
• PKA: 2.46±0.10(Predicted)
• Flash Point: 367.6 °C
• PSA: 108.75000
• Density: 1.389 g/cm³
• LogP: 3.24640
• Storage Temp.: -20°C
• Solubility.: Soluble in DMSO (up to at least 25 mg/ml).
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 352.10592162
• Heavy Atom Count: 26
• Complexity: 508

Purity/Quality:

N-[(4-Hydroxy-1-methyl-7-phenoxy-3-isoquinolinyl)carbonyl]glycine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C2C=C(C=CC2=C(C(=N1)C(=O)NCC(=O)O)O)OC3=CC=CC=C3
• Recent ClinicalTrials: Efficacy and Safety of Roxadustat for Treatment of Anemia in Participants With Lower Risk Myelodysplastic Syndrome With Low Red Blood Cell Transfusion Burden
• Recent EU Clinical Trials: A Phase 1 Crossover Study to Assess the Relative Bioavailability of Roxadustat Following a Single Dose of Pediatric Azo Dye-free Tablet and Pediatric Azo Dye free Mini-tablet (Solid and Suspension) Compared to a Single Dose of Azo Dye-containing Tablet in Healthy Adult Subjects
• Recent NIPH Clinical Trials: The administration study of hematopoietic agents, antidiuretics, plasma substitutes and cortisol synthesis inhibitor in healthy adults
• Description: Roxadustat is an orally administered, small molecule hypoxia-inducible factor (HIF) prolyl hydroxylase inhibitor that is being developed by FibroGen, in collaboration with Astellas and AstraZeneca, for the treatment of anaemia in patients with dialysis-dependent chronic kidney disease (CKD), non-dialysis-dependent CKD and in patients with myelodysplastic syndromes.
• Uses: Roxadustat is a hypoxia-inducible factor (HIF) prolyl hydroxylase inhibitor used to increase white blood cell levels in blood and hematopoietic progenitor cells in bone marrow.

Technology Process of Roxadustat

There total 122 articles about Roxadustat 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: 100.0%

dihydroxy-methyl-borane (13061-96-6) + (1-bromo-4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)glycine methyl ester → [(4-hydroxy-1-methyl-7-phenoxy-isoquinoline-3-carbonyl)-amino]-acetic acid (808118-40-3)

Guidance literature:

With potassium dihydrogenphosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In ethanol; water; at 100 ℃; for 16h; Inert atmosphere;

Reference yield: 99.1%

(1-((dimethylamino)methyl)-4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)glycine → [(4-hydroxy-1-methyl-7-phenoxy-isoquinoline-3-carbonyl)-amino]-acetic acid (808118-40-3)

Guidance literature:

With zinc; at 70 ℃; for 5h; under 760.051 Torr; Temperature;

Reference yield: 98.7%

C33H29N3O5 → [(4-hydroxy-1-methyl-7-phenoxy-isoquinoline-3-carbonyl)-amino]-acetic acid (808118-40-3)

Guidance literature:

With zinc; at 120 ℃; for 5h; under 760.051 Torr;

upstream raw materials:

4-Nitrophthalonitrile

4-phenoxyphthalonitrile

4-phenoxyphthalic acid

4-phenoxyphthalic anhydride

Refernces

• 1、 -. "Preparation method of bleomycin". Paragraph 0027; 0037-0040; 0048-0055; 0061-0066. . Retrieved 2021/04/07.
• 2、 -. "Preparation method of isoquinoline derivative". Paragraph 0075-0080. . Retrieved 2021/02/10.