Cefotaxime 2936433 226092793 2008-07-16T20:07:36Z Gor n bein 5019306 /* Clinical use */ {{drugbox | |image=Cefotaxime.svg |width=300 |IUPAC_name = (6''R'',7''R'',''Z'')-3-(acetoxymethyl)-7-(2-(2-aminothiazol-4-yl)-<br>2-(methoxyimino)acetamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]<br>oct-2-ene-2-carboxylic acid |CAS_number = 63527-52-6 | ATC_prefix=J01 | ATC_suffix=DD01 | PubChem=456256 | DrugBank=APRD00854 | C = 16 | H = 17 | N = 5 | O = 7 | S = 2 |molecular_weight = 455.47 g/mol |bioavailability = n/a |metabolism = [[Liver|Hepatic]] |elimination_half-life = 0.8–1.4 hours |excretion = 50–85% [[Kidney|renal]] |pregnancy_AU = B1 |pregnancy_US = B |legal_AU = S4 |routes_of_administration = [[intravenous therapy|Intravenous]] }} '''Cefotaxime''' ([[International Nonproprietary Name|INN]]) ({{pronEng|sɛfəˈtæksiːm/, /kɛfə-}}) is a third-generation [[cephalosporin]] [[antibiotic]]. Like other third-generation cephalosporins, it has broad spectrum activity against [[Gram positive]] and [[Gram negative]] [[bacteria]]. In most cases, it is considered to be equivalent to [[ceftriaxone]] in terms of safety and efficacy. '''Cefotaxime sodium''' is marketed under various trade names including '''Claforan''' ([[Sanofi-Aventis]]). ==Mechanism of action== Inhibits bacterial cell wall synthesis by binding to one or more of the penicillin-binding proteins (PBPs) which in turn inhibits the final transpeptidation step of peptidoglycan synthesis in bacterial cell walls, thus inhibiting cell wall biosynthesis. Bacteria eventually lyse due to ongoing activity of cell wall autolytic enzymes (autolysins and murein hydrolases) while cell wall assembly is arrested.<ref name="Merck">[http://www.merck.com/mmpe/lexicomp/cefotaxime.html Cefotaxime drug information] </ref> ==Clinical use== Treatment of susceptible infection in respiratory tract, skin and skin structure, bone and joint, urinary tract, gynecologic as well as septicemia, and documented or suspected [[meningitis]]. Active against most gram-negative bacilli (generally ineffective against [[Pseudomonas]]) and gram-positive cocci (not [[enterococcus]]). Active against many penicillin-resistant pneumococci<ref name="Merck"/> (See also [[cephalosporin]]).It has only modest activity against the anaerobic B. fragilis species. ==Chemistry== The ''syn''-configuration of the [[methoxy]][[imino]] moiety confers stability to [[beta lactamase|β-lactamase]] enzymes produced by many [[Gram-negative]] bacteria. Such stability to β-lactamases increases the activity of cefotaxime against otherwise resistant Gram-negative organisms. ==References== {{reflist}} {{CephalosporinAntiBiotics}} [[Category:Cephalosporin antibiotics]] [[Category:Thiazoles]] [[de:Cefotaxim]] [[es:Cefotaxima]] [[fr:Céfotaxime]] [[pl:Cefotaksym]] [[pt:Cefotaxima sódica]] [[th:เซฟโฟแทกซิม]]