Meticillin

From the chemical point of view, the first type of semisynthetic penicillins, undoubtedly, are considered relatively simple derivatives of 6-APA and aromatic or aryloxycar-boxylic acids (benzylpenicillin, phenoxymethylpenicillin, meticillin, naphicillin). 

Kuroda, M. et al. 2001. Whole genome sequencing of meticillin-resistant Staphylococcus aureus. Lancet 357, 1225-1240. 

Occurs with all beta-lactams probably more often with meticillin, nafcillin, oxacillin, second- and third-generation cephalosporins,... 

Benzylpenicillin benethamine Amoxicillin Meticillin (pINN) Ticarcillin (pINN)... 

Acute tubulointerstitial nephritis has been reported in relation to various penicillins, including penicillin G, ampicillin, and amoxicillin (98-102), dicloxacillin (103), meticillin (104-109), nafcillin (110,111), oxacillin (107), and piperacillin (112-114). However, meticillin is the prototype that has caused this reaction more often than any other beta-lactam. 

Meticillin-induced acute interstitial nephritis follows a similar pattern of dose-dependence and time-dependence to that of neutropenia (104,105). This reaction occurred in 16% of all children treated with high-dose meticillin (115). Nephritis occurred after a mean of 17 days and a mean cumulative dose of 120 g. 

Hemorrhagic cystitis has been observed in connection with meticillin (116) and carbenicillin (117). 

Vancomycin is particularly useful in infections caused by meticillin-resistant or penicillinase-producing staphylococci and diphtheroids, as well as in the prophylaxis of bacterial endocarditis and in the treatment of antibiotic-associated colitis. Sufficient fecal concentrations can be achieved with oral therapy. It is poorly absorbed from the gastrointestinal tract and painful when injected intramuscularly. It diffuses moderately well into bone tissue (6). 

Phenol ethers in methanol, particularly those without any other functional groups, have a relatively similar UV spectrum to phenols X max at about 270-285 nm, sometimes with no marked shoulder (meticillin sodium salt [408], verapamil hydrochloride [1416]), sometimes with a faintly defined shoulder (guaifenesin [2406]) and sometimes with a more marked narrow band at X max + approx. 8 nm (chlorphenesin carbamate [1101]). 

Diep BA, GUI SR, Chang RF, Phan TH, Chen JH, Davidson MG, Lin F, Lin J, Carleton HA, Mongodin EF, Sensabaugh GF, Perdreau-Remington F (2006) Complete genome sequence of USA300, an epidemic clone of community-acquired meticillin-resistant Staphylococcus aureus. Lancet 367 731-739... 

The first drugs to be effectively used against bacterial infections were the sulphonamides introduced in the 1930s and followed in the 1940s by the penicillins. More recently, new drugs have been necessary because of the problem of resistance. This is best exemplified by the staphylococcus strains now called MRSA (meticillin resistant Staphylococcus aureus, or multi-resistant Staphylococcus aureus. Meticillin is now unavailable in the United Kingdom). 

Bird, J. and Lubkowski, Z., January 22,2005 Controlling meticillin-resistant Staphylococcus Aureus, aka Superbug , The Lancet. 

Sawano, T Inoue, R Kaito, C Sekimizu, K Hirakawa, H Kuhara, S., Goto, S Yabuzaki, J Kanehisa, M Yamashita, A., Oshima, K., Furuya, K Yoshino, C Shiba, T Hattori, M Ogasawara, N Hayashi, H., and Hiramatsu, K. (2001) Whole genome sequencing of meticillin-resistant Staphylococcus aureus. Lancet 357, 1225-1240. 

Grundmann, H Aires-de-Sousa, M., Boyce, J., and Tiemersma, E. (2006) Emergence and resurgence of meticillin-resistant Staphylococcus aureus as a public-health threat. Lancet 368, 874-885. 

A 76-year-old woman with penicillin and sulfa allergy was given vancomycin for a pacemaker infection with meticillin-sensi-tive S. aureus [98" ]. On day 4 she developed a worsening papular rash and a skin biopsy confirmed a severe leukocytoclastic necrotizing vasculitis, which resolved 5 days after vancomycin withdrawal. 

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