Lonaprisan

Base Information

• Chemical Name: Lonaprisan
• CAS No.: 211254-73-8
• Molecular Formula: C28H29F5O3
• Molecular Weight: 508.528
• European Community (EC) Number: 664-453-1
• UNII: F5Z5EL4D26
• DSSTox Substance ID: DTXSID60893551
• Nikkaji Number: J1.473.678F
• Wikipedia: Lonaprisan
• Wikidata: Q27277684
• NCI Thesaurus Code: C71532
• Pharos Ligand ID: MSPWB2HF8YZG
• ChEMBL ID: CHEMBL146032
• Mol file: 211254-73-8.mol

Synonyms:11-(4-acetylphenyl)-17-hydroxy-17-(1,1,2,2,2-pentafluoroethyl)estra-4,9-dien-3-one;lonaprisan;ZK 230211;ZK-230211;ZK230211

Chemical Property of Lonaprisan

Chemical Property:

• Boiling Point: 601.0±55.0 °C(Predicted)
• PKA: 12.15±0.60(Predicted)
• PSA: 54.37000
• Density: 1.34±0.1 g/cm3(Predicted)
• LogP: 6.71740
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 508.20368559
• Heavy Atom Count: 36
• Complexity: 1020

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=CC=C(C=C1)C2CC3(C(CCC3(C(C(F)(F)F)(F)F)O)C4C2=C5CCC(=O)C=C5CC4)C
• Isomeric SMILES: CC(=O)C1=CC=C(C=C1)[C@H]2C[C@]3([C@@H](CC[C@]3(C(C(F)(F)F)(F)F)O)[C@H]4C2=C5CCC(=O)C=C5CC4)C
• Recent ClinicalTrials: ZK 230211 in Postmenopausal Woman With Metastatic Breast Cancer
• Recent EU Clinical Trials: Randomized phase II study to investigate the efficacy, safety and tolerability of ZK 230211 (25 mg vs. 100 mg) as second-line endocrine therapy for postmenopausal women with hormone receptor-positive metastatic breast cancer

Technology Process of Lonaprisan

There total 6 articles about Lonaprisan 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: 92.0%

5,17α-dihydroxy-17α-(1,1,2,2,2-pentafluoroethyl)-11β-[4-(2,5,5-trimethyl-1,3-dioxan-2-yl)phenyl]-5α-estr-9-en-3-one cyclic 2,2-dimethylpropane-1,3-diyl acetal → 11β-(4-acetylphenyl)-17β-hydroxy-17α-(1,1,2,2,2-pentafluoroethyl)-estra-4,9-dien-3-one (211254-73-8)

Guidance literature:

With 50percent aq. H₂SO₄; In methanol; at 20 ℃; for 2h;

DOI:10.1021/jm001000c

Reference yield:

5-hydroxy-11β-[4-(2,5,5-trimethyl-1,3-dioxan-2-yl)phenyl]-5α-estr-9-ene-3,17-dione cyclic 3-(2,2-dimethylpropane-1,3-diyl acetal) → 11β-(4-acetylphenyl)-17β-hydroxy-17α-(1,1,2,2,2-pentafluoroethyl)-estra-4,9-dien-3-one (211254-73-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 49 percent / MeLi*LiBr / diethyl ether / 1 h / -78 °C

2: 92 percent / 50percent aq. H₂SO₄ / methanol / 2 h / 20 °C

With methyllithium lithium bromide; In methanol; diethyl ether;

DOI:10.1021/jm001000c

Reference yield:

11β-(4-acetylphenyl)-20,20,21,21,21-pentafluoro-17-hydroxy-19-nor-17α-pregna-4,9-dien-3-one ethanol solvate (959141-50-5) → 11β-(4-acetylphenyl)-17β-hydroxy-17α-(1,1,2,2,2-pentafluoroethyl)-estra-4,9-dien-3-one (211254-73-8)

Guidance literature:

In water; at 25 - 85 ℃; Product distribution / selectivity;

upstream raw materials:

11β-(4-acetylphenyl)-20,20,21,21,21-pentafluoro-17-hydroxy-19-nor-17α-pregna-4,9-dien-3-one ethanol solvate

11β-(4-acetylphenyl)-20,20,21,21,21-pentafluoro-17-hydroxy-19-nor-17α-pregna-4,9-dien-3-one methanol solvate

Downstream raw materials:

11β-(4-acetylphenyl)-20,20,21,21,21-pentafluoro-17-hydroxy-19-nor-17α-pregna-4,9-dien-3-one methanol solvate