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Prulifloxacin C화학적 특성, 용도, 생산
개요
Prulifloxacin was launched as the third fluoroquinone. It was introduced in
Japan as an oral treatment for urinary tract infections (UTls), respiratory tract infections
(RTls) and bacterial pneumoniae. It can be synthesized in 10 steps from commercially
available 3,4-difluoroaniline. Key steps involve the cyclization of 6,7-difluoro-rl-hydroxy-2-
thioquinoline-3carboxylic acid ethyl ester with 1 ,I-dibromomethane to give the
corresponding thiazeto-[3,2a]quinoline. Aromatic nucleophilic substitution of the 7-fluoro
atom with piperazine followed by hydrolysis of the ethyl ester and finally alkylation of the
piperazinyl moiety with 4-(bromomethyl)-5-methyl-l ,bdioxol-Bone complete the synthesis.
Prulifloxacin is a lipophilic prodrug, which is rapidly hydrolyzed to the corresponding Ndealkylated
piperazine, NM 394, by paraoxonase type enzymes in blood and liver following
intestinal absorption. The DNA gyrase inhibitor NM 394 accounts for all antimicrobial
activity: it shows a similar or greater activity against gram-positive bacteria compared to
ciprofloxacin, and a greater activity in the case of gram-negative bacteria. In clinical
studies, prulifloxacin has shown good efficacy against UTls and RTls. The drug is mainly
excreted in the urine and in the feces as unchanged NM 394, which has a plasma half-life
of approximately 8 h. Phototoxicity in animal models is less severe than with other
quinolones. Prulifloxacin is well tolerated with an adverse effect profile similar to that of
other fluoroquinolones.
화학적 성질
Off-White Solid
용도
Prulifloxacin is a synthetic chemotherapeutic antibiotic of the fluoroquinolone drug class. Prulifloxacin is a prodrug for active metabolite, Ulifloxacin. Antibacterial.
Pharmaceutical Applications
A lipophilic prodrug which is very rapidly metabolized by esterase into ulifloxacin, a 6-fluoro, 7-piperazinyl thiazetoquinoline. Ulifloxacin is moderately active against Staph. aureus (MIC 0.4–0.8 mg/L) and inactive against Str. pneumoniae (MIC 2–8 mg/L) as well as against Enterococcus spp. Against Enterobacteriaceae (MIC 0.05–0.8 mg/L) and Ps. aeruginosa (MIC 0.2–0.8 mg/L) activity is similar to that of ciprofloxacin. It is active against fastidious Gram-negative bacilli, but not against anaerobes and non-fermentative Gram-negative bacilli. Activity against Acinetobacter spp. is modest. Prulifloxacin is rapidly converted into ulifloxacin and after 3 h is no longer detected in blood. In volunteers receiving a single oral dose, peak plasma concentrations of 0.68 mg/L (300 mg dose) to 1.88 mg/L (for 400 mg dose) were attained between 0.67 and 1.25 h. The mean apparent elimination half-life was 8 h and the mean cumulative elimination rate in urine within 48 h was 31–46%. Other inactive metabolites account for 7% of the dose. Half the administered dose is eliminated in feces within 72 h as ulifloxacin and 4% as prulifloxacin. Protein binding is 45%.
