70458-92-3 Usage
Uses
antibacterial;DNA gyrase inhibitor
Definition
ChEBI: A quinolone that is 4-oxo-1,4-dihydroquinoline which is substituted at positions 1, 3, 6 and 7 by ethyl, carboxy, fluorine, and 4-methylpiperazin-1-yl groups, respectively.
Pharmaceutical Applications
A 6-fluoro, 7-piperazinyl quinoline available for oral and intravenous administration. The in-vitro activity is very similar to that of norfloxacin . It is active against H. ducreyi, V. cholerae and Legionella spp., but Campylobacter and Acinetobacter spp. and pseudomonads are not susceptible. It has poor activity against pneumococci, chlamydiae, mycoplasmas and ureaplasmas. L. monocytogenes, Nocardia spp. and anaerobes are resistant.A plasma concentration of c. 5 mg/L is achieved 1–1.5 h after a 400 mg oral dose. The plasma elimination half-life is 8.5–15 h. It is widely distributed, concentrations in bone, brain, blister fluid, CSF, saliva, sputum and prostate all approximating, and in some cases exceeding, the simultaneous plasma concentration. It is extensively metabolized to the desmethyl (= norfloxacin) and N-oxide derivatives. Some 60–70% of a dose, only about 10% of which is unchanged, appears in the urine; 25% of a dose appears in the feces, a small part contributed by elimination in the bile.The half-life increases with hepatic impairment, but is virtually unaffected by renal failure. In patients on continuous ambulatory peritoneal dialysis (CAPD) given 800 mg followed by 400 mg every 12 h for 10–12 days, there was no significant accumulation of pefloxacin or its metabolite, norfloxacin, but concentrations of pefloxacin N-oxide rose continuously in plasma and dialysate; all concentrations fell rapidly when treatment was discontinued.Adverse reactions are those common to the group . Most common are gastrointestinal tract disturbances, although some typical CNS reactions have been encountered. Skin eruptions (some photosensitive) occur and rashes appeared in about one-third of a group of patients who were given longterm therapy. Clinical uses are similar to those of ofloxacin.
Check Digit Verification of cas no
The CAS Registry Mumber 70458-92-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,0,4,5 and 8 respectively; the second part has 2 digits, 9 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 70458-92:
(7*7)+(6*0)+(5*4)+(4*5)+(3*8)+(2*9)+(1*2)=133
133 % 10 = 3
So 70458-92-3 is a valid CAS Registry Number.
InChI:InChI=1/C17H20FN3O3/c1-3-20-10-12(17(23)24)16(22)11-8-13(18)15(9-14(11)20)21-6-4-19(2)5-7-21/h8-10H,3-7H2,1-2H3,(H,23,24)
70458-92-3Relevant articles and documents
Biophysical models as an approach to study passive absorption in drug development: 6-fluoroquinolones
Merino,Freixas,Del Val Bermejo,Garrigues,Moreno,Pla- Delfina
, p. 777 - 782 (1995)
A preliminary study attempting to assess and explain the intestinal absorption of a series of antibacterial 7-piperazinyl-6-fluoroquinolones is presented. The synthesis, n-octanol partition coefficients, intrinsic rat gut in situ absorption rate constants, and in vitro antibacterial activity data found for these homologous compounds are described. A fluorimetric, reverse- phase HPLC method was performed for the quantification of the quinolones in absorption and partition samples. Equations based on two classic biophysical absorption models are given for predicting the intrinsic absorption features of the series according to the partition data or merely single structural parameters. In situ absorption rate constants were found to increase by a factor of 9.7-13.5 for moderately lipophilic derivatives relative to the simplest compound, while antibacterial activity decreased only by a factor of 4. In vivo absorption tests with two representative members of the series were carried out and the results showed a good accordance with those found in situ. This makes these compounds or related ones with similar partition features excellent candidates for further pharmacokinetic and pharmacological testing. The study can serve as an example of how to prevent potential absorption problems associated with the development of new drugs.
NOVEL METHOD OF SYNTHESIS OF FLUOROQUINOLONES
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Page/Page column 6; 9-10, (2009/04/24)
The invention relates to a method of preparation of fluoroquinolones of formula (I) from compounds of formula (II): in which R1, R2, R3, R4, R5, R6, R7, and X are as defined in Claim 1.
Regioselective nucleophilic substitution of halogen derivatives of 1-substituted 4-oxo-1,4-dihydroquinoline-3-carboxylic acids
Hermecz, Istvan,Vasvari-Debreczy, Lelle,Podanyi, Benjamin,Kereszturi, Geza,Balogh, Maria,Horvath, Agnes,Varkonyi, Peter
, p. 1111 - 1116 (2007/10/03)
The rate of the nucleophilic displacement of the fluoro atom of 7-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate could be enhanced either by the introduction of further fluoro atom(s) into position(s) 6 and/or 8, or by the formation of a boron chelate (e.g. 3). The regioselectivity of the nucleophilic substitution of the chloro atom in 1-substituted 6-fluoro-7-chloro-4-oxo-1,4dihydroquinoline-3-carboxylic acids could also be enhanced by the formation of a boron chelate (e.g. 7).
