Cefonicid

Abstract

Cefonicid is a 'second generation' cephalosporin administered intravenously or intramuscularly. It is similar to cefamandole in its superiority to first generation cephalosporins against several enterobacteriaceae as well as its activity against Haemophilus influenzae, including beta-lactamase-producing strains. Its activity against Staphylococcus aureus is similar to that of cefoxitin and inferior to cefamandole and first generation cephalosporins. It has excellent in vitro activity against Neisseria gonorrhoeae, but is inactive against Pseudomonas, Acinetobacter, Serratia, and Bacteroides fragilis. Due to high achievable plasma concentrations and a relatively long half-life, in most clinical trials cefonicid has been administered once daily. It was comparable in efficacy with cefamandole or cefazolin in the treatment of patients with urinary tract, lower respiratory tract, and soft tissue and bone infections. It has also been compared with penicillin in the treatment of uncomplicated gonorrhoea. Results from a small series of patients with endocarditis appear to indicate that cefonicid should not be used in patients with serious staphylococcal infections. Single doses of cefonicid given preoperatively appear to offer a similar degree of protection against post-surgical infection as multiple doses of other antibiotics, but further data from studies involving larger numbers of patients are needed to confirm these impressions. Patients who require prolonged antibiotic therapy, such as those with osteomyelitis being treated as outpatients after a relatively short inpatient course, could benefit from the once daily dose regimen of cefonicid.

An Ugi Reaction/Intramolecular Cyclization/Oxidation Cascade towards Tetrazole-Linked Dibenzoxazepines

“…The following abbreviations are used for spin multiplicities: s = singlet, d = doublet, t = triplet, q = quartet, quin = quintet, dt = double triplet, dd = doublet of doublets and m = multiplet. Chemical shifts for 13 C NMR spectra are reported in ppm relative to the solvent peak (CDCl 3 : 77.23 ppm, DMSO-d 6 : 39.52 ppm, methanol-d 4 : 49.00 ppm). Mass spectra were measured on a Waters Investigator Supercritical Fluid Chromatograph with a 3100 MS Detector (ESI) and using a solvent system of methanol and CO 2 on a Viridis silica gel column (4.6 × 250 mm, 5 m particle size).…”

“…1 H NMR (500 MHz, DMSO-d 6 ):  = 9.79 (s, 1 H), 7.61-7.48 (m, 2 H), 7.39-7.33 (m, 1 H), 7.27 (s, 1 H), 7.10 (t, J = 7.7 Hz, 1 H), 7.00 (dd, J = 12.1, 8.2 Hz, 1 H), 6.77-6.66 (m, 3 H), 6.57 (t, J = 6.4 Hz, 1 H), 6.43 (t, J = 9.0 Hz, 1 H), 6.38 (dd, J = 8.3, 2.2 Hz, 1 H), 5.97 (s, 1 H), 2.20 (s, 1 H), 1.06 (s, 6 H). 13…”

“…1 H NMR (500 MHz, CDCl 3 ):  = 9.47 (s, 1 H), 7.22-7.17 (m, 2 H), 7.15 (d, J = 7.9 Hz, 1 H), 6.99 (d, J = 1.6 Hz, 1 H), 6.92 (t, J = 8.5 Hz, 1 H), 6.68 (d, J = 6.5 Hz, 1 H), 6.51 (d, J = 6.9 Hz, 1 H), 5.94 (dd, J = 7.0, 3.1 Hz, 1 H), 4.66 (t, J = 4.2 Hz, 1 H), 2.24 (s, 3 H), 2.17-2.07 (m, 2 H), 2.01-1.90 (m, 2 H), 1.75-1.69 (m, 3 H), 1.57-1.45 (m, 1 H), 1.42-1.33 (m, 2 H). 13…”

“…1 H NMR (500 MHz, methanol-d 4 ):  = 7.44 (dd, J = 8.2, 1.6 Hz, 1 H), 7.18 (td, J = 7.7, 1.7 Hz, 1 H), 7.02-6.97 (m, 1 H), 6.94 (td, J = 7.9, 1.5 Hz, 1 H), 6.89-6.85 (m, 2 H), 6.81 (td, J = 8.4, 1.6 Hz, 1 H), 6.73-6.66 (m, 2 H), 2.31-1.99 (m, 2 H), 1.91 (s, 6 H), 0.74 (s, 9 H). 13…”

“…5 Recently, this heterocycle has been investigated more and more in pharmaceutical chemistry. [6][7][8][9] On the other hand, 1,5-disubstituted tetrazoles are bioisosteres of the cis-amide bond of peptides 10,11 and can also be found in various drugs such as cilostazol 12 and the antibiotics cefonicid 13 and latamoxef. 14 However, there are few studies on combining dibenzo[b,f] [1,4]oxazepine and 1,5disubstituted tetrazoles into a bis-heterocyclic system.…”