Ciprofloxacine

This representation is intended to encompass 4-oxo-3-quinolinecarboxyhc acids as well as the corresponding 1,8-naphthyridines, cinnolines, and pyrido[2,3-<55pyrimidines. These classes are illustrated by ciprofloxacin [85721-33-1] (2) (1), naUdixic acid [389-08-2] (3) (2), cinoxacin [28657-80-9] (4) (3), and piromidic acid [19562-30-2] (5) (4), respectively. 

Another important development in the stmcture—activity relationships of quinolone antibacterials came with the introduction of the 1,8-bridged quinolone ofloxacin (6a). In this quinolone, the movement of the ethyl group at the 1-position is restricted by "tying" it to the 8-position in the form of a 1,4-benzoxazine ring. In vitro activity improvements are found that are more or less comparable to the improvements noted with ciprofloxacin (35,41—43). 

The 5-position of quinolones can be substituted by small groups such as halogens, hydroxyl, or amino (54—56). The amino group at this position can be advantageous, particularly when appHed to 6,8-difluoro-7-piperazinyl or 6,8-difluoro-7-pyrrohdinyl quinolones. In contrast to 6,8-difluoro quinolones, when this replacement is appHed to ofloxacin, the resulting derivative has reduced antibacterial activity (57). Replacement of the 5-amino group with methylamine or dimethylamine causes activity to drop substantially. Sparfloxacin [110871-86-8] (21), a representative of 5-amino-6,8-difluoro quinolones, affords modest improvements in gram-positive activity as well as increased in vivo potency when compared with both ciprofloxacin and ofloxacin (54). 

A surprising development involving the 3-position has been presented (61,62). This position traditionally has had a carboxylic acid group and attempts to replace the carboxylate have resulted in lower antibacterial activity. However, it was demonstrated that the carboxylate could be replaced with an isothiazolo ring fused between the 2- and 3-position of the quinolone nucleus. A-62824 [111279-87-9] (22), illustrates this stmctural modification as apphed to ciprofloxacin. 

An illustration of a modified Wallach fluorination is the synthesis of 2 4 di chloro-5-fluorotoluene, an intermediate in the preparation of the fluoroquinolone antibacterial ciprofloxacin This was prepared in 69% overall yield by heating W(2,4-dichloro-5-methylphenyl) N, N dimethyltriazene in anhydrous hydrogen fluoride [44] (equation 11)... 

There are several methods of preparation of antibacterial quinolones, drugs widely used in the therapy of various bacterial diseases. The most general method is based on the nucleophilic cyclization of 2-halobenzoyl derivatives 402, leading to the key intermediates 403. The methodology is exemplified in Scheme 63 by the synthesis of a broad-spectrum drug ciprofloxacin... 

The complexation of 6, ciprofloxacin, and lomefloxacin with metals ions were studied in aqueous solution (pD 2.5 37 °C) by and NMR spectroscopy (99MI18). Titration experiments have revealed that the binding ability of 6 towards Al " " ion is much stronger than that of ciprofloxacin and lomefloxacin. Other metal ions (Ca " " and Mg " ") formed much weaker complexes. 

Theophylline Ciprofloxacin, fluvoxamine, etc. CYP1A2 Theophylline toxicity... 

It has been shown that an AAC enzyme variant (AAC (6 )-Ib-cr, cr for ciprofloxacin resistance) found in various Enterobacteriaceae is capable of A-acetylating fluoroquinolones with an unmodified piperazinyl substituent at the amino nitrogen. Although the increase in MIC is low, this plasmid encoded quinolone resistance determinant can augment further development of clinically relevant resistance. 

The fluoroquinolones include ciprofloxacin (Cipro), enoxacin (Penetrex), gatifloxacin (Tequin), lome-floxacin (Maxaquin), moxifloxacin (Avelox), ofloxacin (Floxin), and sparfloxacin (Zagain). 

The fluoroquinolones are used in the treatment of infections caused by susceptible microorganisms. The fluoroquinolones are effective in the treatment of infections caused by gram-positive and gram-negative microorganisms. They are primarily used in the treatment of susceptible microorganisms in lower respiratory infections, infections of the skin, urinary tract infections, and sexually transmitted diseases. Ciprofloxacin, norfloxacin, and ofloxacin are available in ophthalmic forms for infections in the eyes. 

Ciprofloxacin, gatifloxacin, and ofloxacin are the only fluoroquinolones given intravenously (IV). None of the fluoroquinolones are given intramuscularly (IM). 

Ms. Carson is seen in the outpatient clinic for a severe respiratory infection and is prescribed ciprofloxacin. Discuss what you would include in the teaching plan for this patient. 

A patient is prescribed ciprofloxacin for a severe respiratory infection. What serious adverse reaction(s)... 

There is an increased risk of CNS depression when tiie dopamine receptor agonists are administered witii otiier CNS depressants. When administered witii levodopa, the dopamine receptor agonists increase the effects of levodopa (a lower dosage of levodopa may be required). hi addition, when the dopamine receptor agonists are administered with levodopa, there is an increased risk of hallucinations. When administered witii ciprofloxacin, there is an increased effect of the dopamine receptor agonist. 

Hallett, P., Mehlert, A., Maxwell, A. (1990). E. colt cells resistant to the DNA gyrase inhibitor, ciprofloxacin, overproduce a 60 IcD protein homologous to GroEL. Mol. Microbiol. 4,345-353. 

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