Cefotaxime

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Cefotaxime
Systematic (IUPAC) name
(6R,7R,Z)-3-(acetoxymethyl)-7-(2-(2-aminothiazol-4-yl)- 2-(methoxyimino)acetamido)-8-oxo-5-thia-1-azabicyclo[4.2.0] oct-2-ene-2-carboxylic acid
Identifiers
CAS number	63527-52-6
ATC code	J01DD01
PubChem	456256
DrugBank	APRD00854
Chemical data
Formula	C16H17N5O7S2
Mol. mass	455.47 g/mol
Pharmacokinetic data
Bioavailability	n/a
Metabolism	Hepatic
Half life	0.8–1.4 hours
Excretion	50–85% renal
Therapeutic considerations
Pregnancy cat.	B1(AU) B(US)
Legal status	Prescription Only (S4)(AU)
Routes	Intravenous

Cefotaxime (INN) (pronounced /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).

Contents 1 Mechanism of action 2 Clinical use 3 Chemistry 4 References

[edit] 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.^[1]

[edit] 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 (not Pseudomonas) and gram-positive cocci (not enterococcus). Active against many penicillin-resistant pneumococci^[1] (See also cephalosporin).

[edit] Chemistry

The syn-configuration of the methoxyimino moiety confers stability to 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.

[edit] References

v • d • e Antibacterials for systemic use: beta-lactam antibiotics - cephalosporins and related (J01D) First generation Cefacetrile, Cefadroxil, Cefalexin, Cefaloglycin, Cefaloridine, Cefalotin, Cefapirin, Cefatrizine, Cefazedone, Cefazolin, Cefradine, Cefroxadine, Ceftezole Second generation Cefaclor, Cefamandole, Cefmetazole, Cefonicid, Ceforanide, Cefotiam, Cefprozil, Cefuroxime Third generation Cefdinir, Cefditoren, Cefetamet, Cefixime, Cefmenoxime, Cefodizime, Cefoperazone, Cefotaxime, Cefpiramide, Cefpodoxime, Cefsulodin, Ceftazidime, Ceftibuten, Ceftizoxime, Ceftriaxone, Latamoxef Fourth generation Cefepime, Cefozopran, Cefpirome, Cefquinome Fifth generation Ceftobiprole Other beta-lactam antibacterials Monobactams (Aztreonam), Carbapenems (Parenteral - Doripenem, Ertapenem, Imipenem, Meropenem, Panipenem, Oral - Faropenem)