Delafloxacin

Base Information

• Chemical Name: Delafloxacin
• CAS No.: 189279-58-1
• Deprecated CAS: 579508-20-6
• Molecular Formula: C₁₈H₁₂ClF₃N₄O₄
• Molecular Weight: 440.766
• UNII: 6315412YVF
• DSSTox Substance ID: DTXSID40172331
• Nikkaji Number: J1.257.530K
• Wikipedia: Delafloxacin
• Wikidata: Q5253067
• NCI Thesaurus Code: C87390
• RXCUI: 1927663
• Metabolomics Workbench ID: 153018
• ChEMBL ID: CHEMBL2105637
• Mol file: 189279-58-1.mol

Synonyms:1-(6-amino-3,5-difluoropyridin-2-yl)-8-chloro-6-fluoro-7-(3-hydroxyazetidin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid;3-quinolinecarboxylic acid, 1-(6-amino-3,5-difluoro-2-pyridinyl)-8-chloro-6-fluoro-1,4-dihydro-7-(3-hydroxy-1-azetidinyl)-4-oxo-;ABT 492;ABT-492;ABT492;Baxdela;delafloxacin;RX-3341

Chemical Property of Delafloxacin

Chemical Property:

• Melting Point: 238-241℃
• Boiling Point: 698.5 °C at 760 mmHg
• PKA: 5.49±0.50(Predicted)
• Flash Point: 376.2 °C
• PSA: 121.68000
• Density: 1.796 g/cm³
• LogP: 2.56390
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Very Slightly, Heated, Sonicated)
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 3
• Exact Mass: 440.0499171
• Heavy Atom Count: 30
• Complexity: 755

Purity/Quality:

99% ^*data from raw suppliers

Delafloxacin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antiinfective Agents
• Canonical SMILES: C1C(CN1C2=C(C=C3C(=C2Cl)N(C=C(C3=O)C(=O)O)C4=C(C=C(C(=N4)N)F)F)F)O
• Recent ClinicalTrials: Delafloxacin IV and OS Administration Compared to Best Available Therapy in Patients With Surgical Site Infections
• Recent EU Clinical Trials: A randomized, observer-blinded, active-controlled, Phase IIIb study to compare IV / Oral delafloxacin fixed-dose monotherapy with best available treatments in a microbiologically enriched population with surgical site infections
• Uses: Delafloxacin is a potent agent and broad-spectrum anionic fluoroquinolone against Streptococcus pneumoniae and diverse group of pathogens.

Technology Process of Delafloxacin

There total 28 articles about Delafloxacin 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: 94.0%

1-(6-amino-3,5-difluoro-2-pyridyl)-8-chloro-6-fluoro-1,4-dihydro-7-(3-hydroxy-1-azetidinyl)-4-oxo-3-quinolinecarboxylic acid ethyl ester → delafloxacin (189279-58-1)

Guidance literature:

With sodium hydroxide; In ethanol; water; at 20 - 30 ℃; for 3h;

Reference yield: 94.0%

1-(6-amino-3,5-difluoropyridin-2-yl)-8-chloro-6-fluoro-7-(3-isobutyryloxyazetidin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester (875712-90-6) → delafloxacin (189279-58-1)

Guidance literature:

With isopropyl alcohol; sodium hydroxide;

Reference yield: 90.0%

1-(6-amino-3,5-difluoropyridin-2-yl)-6-fluoro-7-(3-isobutyryloxyazetidin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester (442526-91-2) → delafloxacin (189279-58-1)

Guidance literature:

With N-chloro-succinimide; sulfuric acid; In ethyl acetate; at 20 ℃; Cooling with ice; Large scale;

upstream raw materials:

1-Methylpyrrolidine

1-(6-amino-3,5-difluoro-2-pyridinyl)-8-chloro-6,7-difluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid

ethyl 5-amino-1-(6-amino-3,5-difluoropyridin-2-yl)-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

azetion-3-ol hydrochloride

Downstream raw materials:

1-(6-amino-3,5-difluoro-2-pyridinyl)-8-chloro-6-fluoro-1,4-dihydro-7-(3-hydroxy-1-azetidinyl)-4-oxo-3-quinolinecarboxylic acid 1-deoxy-1-(methylamino)-D-glucitol

Refernces

• 1、 -. "Preparation of deller floxacin and intermediate thereof". . . Retrieved 2018/05/30.
• 2、 -. "Preparation method of high-purity delafloxacin meglumine salt". Paragraph 0030. . Retrieved 2017/04/27.