Pazufloxacin

Base Information

• Chemical Name: Pazufloxacin
• CAS No.: 127045-41-4
• Molecular Formula: C₁₆H₁₅FN₂O₄
• Molecular Weight: 318.305
• European Community (EC) Number: 635-036-1
• UNII: 4CZ1R38NDI
• DSSTox Substance ID: DTXSID5046697
• Nikkaji Number: J523.176K
• Wikipedia: Pazufloxacin
• Wikidata: Q3898423
• NCI Thesaurus Code: C66331
• Metabolomics Workbench ID: 144350
• ChEMBL ID: CHEMBL240163
• Mol file: 127045-41-4.mol

Synonyms:10-(1-aminocyclopropyl)-9-fluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido(1,2,3-d,e)(1,4)benzoxazinecarboxylic acid;pazufloxacin;T 3761;T-3761

Chemical Property of Pazufloxacin

Chemical Property:

• Appearance/Colour: like white to light yellow crystalline
• Vapor Pressure: 4E-12mmHg at 25°C
• Melting Point: 269-271 °C
• Refractive Index: 1.692
• Boiling Point: 531.5 °C at 760 mmHg
• PKA: 5.05±0.40(Predicted)
• Flash Point: 275.2 °C
• PSA: 94.55000
• Density: 1.56 g/cm³
• LogP: 2.44030
• Storage Temp.: 2-8°C
• Solubility.: Aqueous Base (Slightly, Sonicated), DMSO (Slightly, Heated), Methanol (Slightly,
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 318.10158513
• Heavy Atom Count: 23
• Complexity: 603

Purity/Quality:

99% ^*data from raw suppliers

Pazufloxacin VETRANAL ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,C,F
• Hazard Codes: Xn,C,F
• Statements: 20/21/22-34-11
• Safety Statements: 36/37-45-36/37/39-26-16

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1COC2=C3N1C=C(C(=O)C3=CC(=C2C4(CC4)N)F)C(=O)O
• Isomeric SMILES: C[C@H]1COC2=C3N1C=C(C(=O)C3=CC(=C2C4(CC4)N)F)C(=O)O
• Recent ClinicalTrials: Efficacy of the Ophthalmic Pazufloxacin 0.6% for Bacterial Conjunctivitis, Compared to Gatifloxacin 0.3%.
• Recent NIPH Clinical Trials: Specific post-marketing surveillance of pazufloxacin (Pasil), an injectable antimicrobial
• Description: Pazufloxacin is a fluoroquinolone with a 1-aminocyclopropyl substituent at C10 position. The presence of aminoacyl group at C-10 is a unique feature of the molecule imparting potent broad spectrum activity against gram-positive and gram-negative bacteria. This activity is based on the inhibition of bacterial DNA gyrase. Pazufloxacin is used as an injectable antibiotic with bacterial effect against cephalosporin-resistant, carbapenem-resistance, and aminoglycoside resistant strains of bacteria. The adverse effects of pazufloxacin, such as drug-induced convulsion and hypotension are less than those of other conventional injectable fluoroquinolones. Pazufloxacin is a novel quinolone marketed for the treatment of bacterial infections in Japan. This tricyclic fluoro-quinolone can be synthesized in 11 steps from commercially available 2,3,4,5tetrafluorobenzoic acid. The cyclopropyl substituent is first introduced in 6 steps including 4-F-substitution with tert-butylcyanoacetate, decarboxylation, aa alkylation with 1 ,Zdibromoethane, partial nitrile hydrolysis and Hoffmann-rearrangement. The pyridoxazine ring is then introduced in 5 steps including 6-ketoester formation and pryridoxazine annulation. Pazufloxacin displays a broad spectrum activity against Grampositive and Gram-negative bacteria, although it is less active that ciprofloxacin against pneumococci and is not active against ciprofloxacin-resistant isolates. In patients with gonococcal urethritis a high prevalence of fluoroquinolone-resistant N. gonorrhoeae isolates with the Ser-91-to-Phe mutation in GyrA was observed. However, good clinical responses have been seen in clinical trials of patients with urinary tract infections and to a lesser extent with respiratory tract infections. Pazufloxacin is mainly excreted in urine with a short half-life (2-2.5 h). It has a phototoxicity equal to that of ciprofloxacin and its adverse effect profile resembles that of other quinolones.
• Uses: Pazufloxacin is a potential antimicrobial and/or antiviral agent. antibactierial

Technology Process of Pazufloxacin

There total 19 articles about Pazufloxacin 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:

10-(1-benzyloxycarbonylaminocyclopropyl)-9-fluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido<1,2,3-de><1,4>benzoxazine-6-carboxylic acid (127046-25-7) → 10-(1-aminocyclopropyl)-9-fluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido<1,2,3-de><1,4>benzoxazine-6-carboxylic acid (127045-41-4,166665-94-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In acetic acid; under 760 Torr; Yield given;

DOI:10.1248/cpb.42.2063

Reference yield:

(R)-9-(1-Benzyloxycarbonylamino-cyclopropyl)-8-fluoro-3-methyl-6-oxo-2,3-dihydro-6H-1-oxa-3a-aza-phenalene-5-carboxylic acid → (R)-10-(1-aminocyclopropyl)-9-fluoro-9-fluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido<1,2,3-de>-1,4-benzoxazine-6-carboxylic acid (127045-41-4,166665-94-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In acetic acid; for 2h; under 760 Torr; Yield given;

DOI:10.1248/cpb.42.2569

Reference yield:

(S)-9-(1-Benzyloxycarbonylamino-cyclopropyl)-8-fluoro-3-methyl-6-oxo-2,3-dihydro-6H-1-oxa-3a-aza-phenalene-5-carboxylic acid → pazufloxacin (127045-41-4,166665-94-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In acetic acid; for 2h; under 760 Torr; Yield given;

DOI:10.1248/cpb.42.2569

upstream raw materials:

10-(1-benzyloxycarbonylaminocyclopropyl)-9-fluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido<1,2,3-de><1,4>benzoxazine-6-carboxylic acid

2,3,4,5-tetrafluorobenzoic acid

ethyl 2,3,4,5-tetrafluorobenzenecarboxylate

ethyl 4-carboxymethyl-2,3,5-trifluorobenzoate

Downstream raw materials:

ethyl (S)-9-fluoro-3,7-dihydro-3-methyl-10-(1-aminocyclopropyl)-7-oxo-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylate

Refernces

• 1、 Todo,Takagi,Iino,Fukuoka,Takahata,Okamoto,Saikawa,Narita. "Pyridonecarboxylic acids as antibacterial agents. IX. Synthesis and structure-activity relationship of 3-substituted 10-(1-aminocyclopropyl)-9-fluoro-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de] -1,4-benzoxazine-6-carboxylic acids and their 1-thio and 1-aza anal". . p. 2569 - 2574. Retrieved 2007/10/02.