Ciprofloxacin, structure

The complex behaviour of pharmaceuticals in the sewage network and during subsequent wastewater treatment is correlated to the nature of their molecular structure, which may contain concomitant acidic and basic functional groups, as in the case of both ciprofloxacin and ceftazidime. This implies that these molecules may be considered as neutral, cationic, anionic or zwitterionic [53], according to the particular environmental conditions, which will consequently affect their behaviour. 

A wide variety of organotin compounds developed by Carraher, Sabir, Roner, and others based on known antiviral drugs such as acyclovir and known antibacterial agents such as ciprofloxacin, norfloxacin, cephalexin (structure 11.21), and ampicillin inhibit a wide variety of viruses including ones responsible for many of the common colds, chicken pox, small pox, shingles, and herpes simplex. 

Ciprofloxacin (Cipro, Cipro XR, Proquin XR) [Antibiotic/ Fluoroquinolone] Uses Rx lower resp tract, sinuses, skin skin structure, bone/joints, urinary tract Infxns including prostatitis Action Quinolone antibiotic DNA gyrase Dose Adults. 250-750 mg PO ql2h XR 500-1000 mg PO q24h or 200-400 mg IV ql2h in renal impair Caution [C, /-] Children <18 y Contra Component sensitivity Disp Tabs, susp, inj SE Restlessness, N/V/D, rash, ruptured tendons, T LFTs Interactions T Effects Wf probenecid T effects OF diazepam, theophylline, caffeine, metoprolol, propranolol, phenytoin, warfarin effects W/ antacids, didanosine, Fe salts. Mg, sucralfate, Na bicarbonate,... 

Contraindications Hypersensitivity to ciprofloxacin or other quinolones for ophthalmic administration vaccinia, varicella, epithelial herpes simplex, keratitis, mycobacterial infection, fungal disease of ocular structure, use after uncomplicated removal of a foreign body... 

Dimensional structures of small molecules that exhibit IL-1 modulating activities. They are tenidap, ciprofloxacin, 3-Deazaadenosine, (SK F 86002), E5110, DMARDs (Chloroquine, Auranofin, Sodium aurothiomalate and Dexamethasone) tiaprofenic acid, dexamethasone, tricyclic-ylidene-acetic acid and its derivative, Probucol, eicosapentenoic acid + docosahexenoic, pentoxifylline, Denbufylline, and Romazarit (Ro-31-3948). 

Fig. 18 Chemical structures of ciprofloxacin and its ferrocenyl conjugates. Doxycycline is the reference compound...

Introduction of the first fluorinated quinolone, norfloxacin [nor FLOX a sin], has been rapidly followed by new members of this class. These agents are totally synthetic and are closely related structurally to an earlier quinolone, nalidixic acid [nal i DIX ik]. The principal member of this group is ciprofloxacin [sip ro FLOX a sin], which has the widest clinical application. Other antibiotics in this group available in the United States are primarily employed to treat urinary infections (Figure 32.1). It seems likely that the size of this class of antibiotics will increase due to its wide antibacterial spectrum, favorable pharmacokinetic properties and relative lack of adverse reactions. Unfortunately, their overuse has already led to the emergence of resistant strains resulting in limitations to their clinical usefulness. 

The evolution of the quinolones, which began with nalidixic acid and has produced the modem fluoroquinones moxifloxacin, gatifloxacin and gemifloxacin, was based not only on modifications of the basic quinolone structure but also on the development of new cyclic amines for the 7-position. The cyclopropyl radical, which was introduced for the first time in ciprofloxacin, remains the most effective substituent for the 1-position. Moxifloxacin is an 8-methoxy fluoroquinolone with a novel enantiomerically pure S,S-2,8-diazabicyclo[4.3.0]non-8-yl radical in the 7-position. 

Quinolones are structurally related to nalidixic acid the names of fhe mosf recently introduced members of the group end in -oxacin, e.g. ciprofloxacin. They acf by preventing DNA replication. 

Animal studies show that the propensity to induce tendon lesions varies among fluoroquinolones. Fleroxacin, pefloxacin, levofloxacin, and ofloxacin were the most toxic, while enoxacin, norfloxacin, and ciprofloxacin had little or no effect (92). The structure of the substituent at... 

Co-administration of fenbufen and fluoroquinolones has been associated with seizures (141). The structure at the 7-position greatly affects the risk of NSAID-potentiated nervous system effects. Fluoroquinolones with unsubstituted piperazinyl rings (ciprofloxacin, enox-acin, and norfloxacin) have a strong interaction with NSAIDs (142). The increased risk of seizures is not caused by increased serum concentrations of fluoroquinolones, since their pharmacokinetics are not altered by NSAIDs (143). The mechanism has been suggested to be facilitation by fenbufen of the fluoroquinolone-induced inhibition of GABAa receptor function in the hippocampus and frontal cortex (144). 

Nicodemo AC, Robledo JA, Jasovich A, Neto W. A multicentre, double-blind, randomised study comparing the efficacy and safety of oral levofloxacin versus ciprofloxacin in the treatment of uncomplicated skin and skin structure infections. Int J Clin Pract 1998 52(2) 69-74. 

Chemical Structure C17H18FN3O3-HCl H2O. Ciprofloxacin has a fluorine atom at the 6-position, a piperazine moiety at the 7-position, and a cyclopropyl ring at the 1-position... 

As far as synthetic agents were concerned, isoniazid (a pyridine hydrazide structure) was found to be effective against human tuberculosis in 1952, and in 1962 nalidixic acid (Fig. 10.74) (the first of the quinolone antibacterial agents) was discovered. A second generation of this class of drugs was introduced in 1987 with ciprofloxacin (Fig. 10.74). 

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