Pazufloxacin

Pazufloxacin Basic information
Description References
Product Name:Pazufloxacin
Synonyms:PAZUFLOXAXIN;T-3761;(s)-yclopropyl)-9-fluoro-3-methyl-7-oxo;Pazufloxacinmyesylate;(3S)-10-(1-AMINOCYCLOPROPYL)-9-FLUORO-2,3-DIHYDRO-3-METHYL-7-OXO-7H-PYRIDO[1,2,3-DE]-1,4-BENZOXAZINE-6-CARBOXYLIC ACID;ALKALYL;Pazufloxaxin mesilate;PAZUFLOXACIN 98+%
CAS:127045-41-4
MF:C16H15FN2O4
MW:318.3
EINECS:635-036-1
Product Categories:BacteriostaticAntibiotics;ChinolonesAlphabetic;PA - PENAnalytical Standards;Pharmacology Standards;Antibiotics;Chemical Structure;Chromatography;P;Principle;API's
Mol File:127045-41-4.mol
Pazufloxacin Structure
Pazufloxacin Chemical Properties
Melting point 269-271°C
alpha D25 -88.0° (c = 0.5 in 0.05N aq NaOH)
Boiling point 531.5±50.0 °C(Predicted)
density 1.56
storage temp. 2-8°C
solubility Aqueous Base (Slightly, Sonicated), DMSO (Slightly, Heated), Methanol (Slightly)
pka5.05±0.40(Predicted)
form neat
color Off-White to Pale Yellow
CAS DataBase Reference127045-41-4(CAS DataBase Reference)
Safety Information
Hazard Codes Xn,C,F
Risk Statements 20/21/22-34-11
Safety Statements 36/37-45-36/37/39-26-16
WGK Germany 3
RTECS UU8815300
ToxicityLD50 i.v. in male mice: >500 mg/kg (Todo)
Pazufloxacin Usage And Synthesis
DescriptionPazufloxacin 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.
References[1] A. Vora, Pazufloxacin, tracked from www.japi.org on 16.07.2017
[2] Jeffrey K. Aronson, Meyler’s Side Effects of Antimicrobial Drugs, 2009
[3] Satoshi Watabe, Yoshiaki Yokoyama, Kazuyuki Nakazawa, Kimikazu Shinozaki, Rika Hiraoka, Kei Takeshita and Yukio Suzuki, Simultaneous measurement of pazufloxacin, ciprofloxacin, and levofloxacin in human serum by high-performance liquid chromatography with fluorescence detection, Journal of Chromatography B, 2010, vol. 878, 1555-1561

DescriptionPazufloxacin 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.
OriginatorToyama (Japan)
UsesPazufloxacin is a potential antimicrobial and/or antiviral agent.
Usesantibactierial
DefinitionChEBI: LSM-5745 is a member of quinolines.
Brand namePasil, Pazucross
Pharmaceutical ApplicationsA tricyclic fluoroquinolone, formulated as mesylate and hydrochloride salts for oral or parenteral use or as a methane sulfonate (eye ointment).
It displays good activity in vitro against methicillin susceptible Staph. aureus (MIC 0.2 mg/L), but is inactive against Str. pyogenes, Str. pneumoniae (MIC ≥4 mg/L) and enterococci. L. pneumophila is inhibited by 0.03 mg/L. Activity against Enterobacteriaceae, fastidious Gram-negative bacilli, Ps. aeruginosa and Acinetobacter spp. is similar to that of ofloxacin. It is weakly active against Sten. maltophilia and Burkholderia cepacia (MIC c. 2 mg/L). Against M. tuberculosis, MICs range from 0.8 to 4 mg/L. It is inactive against anaerobes.
After oral doses of 100 or 400 mg, peak plasma concentrations range from 0.94 mg/L (100 mg) to 4.5 mg/L (400 mg) after <1 h. The apparent elimination half-life is around 2 h. Most of the administered dose is eliminated in urine, about 70% within 24 h. Four metabolites have been reported. In elderly patients, according to the renal function, the peak plasma concentration may be elevated (up to 5.6 mg/L) and significantly delayed (2–6 h). The plasma protein binding ranges from 17% to 28%.

Methyl 1-(2-METHYLPHENOXY)-2-PROPANAMINE (1S)-(2-Fluoro-6-methoxyphenyl)ethylamine 3-(3-ETHOXYPHENYL)PROPIONIC ACID Pazufloxacin (R)-1-(2-Fluorophenyl)ethylamine Benzenemethanamine, α-methyl-4-propyl-, (αS)- N-METHYLCARVACRYLAMINE Tribenuron methyl 3'-FLUORO-4'-METHYLACETOPHENONE Pazufloxacin mesilate Lithium diisopropylamide Thiophanate-methyl 2-Aminopyridine 3-METHYL-3,4-DIHYDRO-2H-1,4-BENZOXAZINE Methyl salicylate 2-CYCLOPROPYLPHENOL 4-Dimethylaminopyridine

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