Delafloxacin Meglumine

Base Information

• Chemical Name: Delafloxacin Meglumine
• CAS No.: 352458-37-8
• Molecular Formula: C₇H₁₇NO₅*C₁₈H₁₂ClF₃N₄O₄
• Molecular Weight: 635.982
• UNII: N7V53U4U4T
• ChEMBL ID: CHEMBL2105638
• DSSTox Substance ID: DTXSID90188740
• NCI Thesaurus Code: C174746
• RXCUI: 1927662
• Wikidata: Q27284685
• Mol file: 352458-37-8.mol

Synonyms:Delafloxacin meglumine;352458-37-8;Delafloxacin (meglumine);RX-3341 meglumine;WQ-3034 meglumine;ABT-492 meglumine;Delafloxacin meglumine [USAN];N7V53U4U4T;DTXSID90188740;UNII-N7V53U4U4T;1-Deoxy-1-(methylamino)-D-glucitol 1-(6-amino-3,5-difluoropyridin-2-yl)-8-chloro-6-fluoro-7-(3-hydroxyazetidin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylate (salt);D-Glucitol, 1-deoxy-1-(methylamino)-, 1-(6-amino-3,5-difluoro-2-pyridinyl)-8-chloro-6-fluoro-1,4-dihydro-7-(3-hydroxy-1-azetidinyl)-4-oxo-3-quinolinecarboxylate (salt);Delafloxacin meglumine (USAN);Delafloxacin meglumine (ABT492 meglumine;WQ-3034 meglumine);(2R,3R,4R,5S)-6-(Methylamino)hexane-1,2,3,4,5-pentaol 1-(6-amino-3,5-difluoropyridin-2-yl)-8-chloro-6-fluoro-7-(3-hydroxyazetidin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylate;1-(6-amino-3,5-difluoropyridin-2-yl)-8-chloro-6-fluoro-7-(3-hydroxyazetidin-1-yl)-4-oxoquinoline-3-carboxylic acid;(2R,3R,4R,5S)-6-(methylamino)hexane-1,2,3,4,5-pentol;Baxdela (TN);ABT492 meglumine;C25H29ClF3N5O9;SCHEMBL300983;CHEMBL2105638;DTXCID50111231;DELAFLOXACIN MEGLUMINE [MI];EX-A3992;HY-14814A;s4488;WQ-3034 AND ABT-492;AKOS025404885;CS-1479;DELAFLOXACIN MEGLUMINE [WHO-DD];AC-36496;BS-16614;DELAFLOXACIN MEGLUMINE [ORANGE BOOK];ABT-492;RX-3341;WQ-3034;Baxdela;D09331;D70784;A874684;Q27284685;(2R,3R,4R,5S)-6-(methylamino)hexane-1,2,3,4,5-pentaol 8-chloro-1-(3,5-difluoro-6-imino-1,6-dihydropyridin-2-yl)-6-fluoro-7-(3-hydroxyazetidin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

Chemical Property of Delafloxacin Meglumine

Chemical Property:

• PSA: 234.86000
• LogP: -0.40350
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Hydrogen Bond Donor Count: 9
• Hydrogen Bond Acceptor Count: 17
• Rotatable Bond Count: 9
• Exact Mass: 635.1605897
• Heavy Atom Count: 43
• Complexity: 889

Purity/Quality:

99%Min. ^*data from raw suppliers

(2R,3R,4R,5S)-2,3,4,5-Tetrahydroxy-6-(methylamino)hexyl1-(6-amino-3,5-difluoropyridin-2-yl)-8-chloro-6-fluoro-7-(3-hydroxyazetidin-1-yl)-4-oxo-1,4-dihydroquin 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNCC(C(C(C(CO)O)O)O)O.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
• Isomeric SMILES: CNC[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.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 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
• Description: Delafloxacin meglumine (Baxdela, WQ-3034, ABT-492, RX-3341; Melinta Therapeutics) was approved by the U.S. Food and Drug Administration (FDA) in June 2017 for the treatment of acute bacterial skin and skin structure infections on the basis of data from two phase III trials.
• Uses: Delafloxacin is a broad-spectrum anionic fluoroquinolone and its distinct chemical structure increases its potency in acidic environments. It is known to inhibit DNA replication and repair by targeting DNA gyrase and topoisomerase IV. Delafloxacin is administered via both oral and parenteral routes. It has potent activity against methicillin-resistant Staphylococcus aureus and Streptococci, and is also effective against Enterobacteriaceae and Pseudomonas aeruginosa.

Technology Process of Delafloxacin Meglumine

There total 10 articles about Delafloxacin Meglumine 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: 92.3%

1-deoxy-1-(methylamino)-D-glucitol (6284-40-8,97780-33-1) + delafloxacin (189279-58-1) → 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 (352458-37-8)

Guidance literature:

In water; at 20 ℃; Temperature; Solvent; Large scale;

Reference yield: 72.9%

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 + 1-deoxy-1-(methylamino)-D-glucitol (6284-40-8,97780-33-1) → 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 (352458-37-8)

Guidance literature:

In water; at 38 - 60 ℃; for 24h; Large scale;

DOI:10.1021/op060054e

Reference yield:

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) → 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 (352458-37-8)

Guidance literature:

Multi-step reaction with 3 steps

1: N-chloro-succinimide; sulfuric acid / ethyl acetate; acetic acid methyl ester / 17 °C / Large scale

2: potassium hydroxide / isopropyl alcohol / 50 °C / Large scale

3: water / 24 h / 38 - 60 °C / Large scale

With N-chloro-succinimide; sulfuric acid; potassium hydroxide; In acetic acid methyl ester; water; ethyl acetate; isopropyl alcohol;

DOI:10.1021/op060054e

upstream raw materials:

1-deoxy-1-(methylamino)-D-glucitol

delafloxacin

1-(6-amino-3,5-difluoropyridin-2-yl)-6-fluoro-7-(3-isobutyryloxyazetidin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

C₁₇H₁₁F₄N₃O₃

Refernces

• 1、 -. "A crystal form L of a delafloxacin meglumine salt and a preparation method thereof". Paragraph 0031-0037; 0072; 0073; 0076; 0077. . Retrieved 2019/11/29.
• 2、 -. "[...] Meglumine crystalline form I and its preparation method". Paragraph 0037-0038; 0040; 0041; 0043; 0045; 0048. . Retrieved 2017/08/31.