Ceftazidime

Ceftazidime

Systematic (IUPAC) name
(6R,7R,Z)-7-(2-(2-aminothiazol-4-yl)- 2-(2-carboxypropan-2-yloxyimino)acetamido)-8-oxo- 3-(pyridinium-1-ylmethyl)-5-thia-1-aza-bicyclo[4.2.0] oct-2-ene-2-carboxylate
Identifiers
CAS number	72558-82-8
ATC code	J01DD02
PubChem	91713
DrugBank	APRD00857
ChemSpider	16744282
Chemical data
Formula	C22H22N6O7S2
Mol. mass	546.58 g/mol
SMILES	eMolecules & PubChem
Pharmacokinetic data
Bioavailability	91% (IM)
Metabolism	negligible
Half life	1.6–2 hours
Excretion	90–96% renal
Therapeutic considerations
Pregnancy cat.	B1(AU) B(US)
Legal status	Prescription Only (S4)(AU)
Routes	Intravenous, intramuscular
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Ceftazidime (INN) (pronounced /sɛfˈtæzɨdiːm/) is a third-generation cephalosporin antibiotic. Like other third-generation cephalosporins, it has broad spectrum activity against Gram-positive and Gram-negative bacteria. Unlike most third-generation agents, it is active against Pseudomonas aeruginosa, however it has weaker activity against Gram-positive microorganisms and is not used for such infections. Ceftazidime pentahydrate is marketed under various trade names including Cefzim (Pharco B International), Fortum (GSK), and Fortaz. It is also sometimes referred to as the "Tasmanian Devil," due to its fairly powerful anti-pseudomonal activity.

Clinical use

Ceftazidime is usually reserved for the treatment of infections caused by Pseudomonas aeruginosa. It is also used in the empirical therapy of febrile neutropenia, in combination with other antibiotics. It is usually given IV or IM every 8–12 hours (2 - 3 times a day), with dosage varying by the indication, infection severity, and/or renal function of the recipient. It is also first line treatment for the rare tropical infection, melioidosis.^[1]

Chemistry

In addition to the syn-configuration of the imino side chain, compared to other third-generation cephalosporins, the more complex moiety (containing two methyl and a carboxylic acid group) confers extra stability to β-lactamase enzymes produced by many Gram-negative bacteria. The extra stability to β-lactamases increases the activity of ceftazidime against otherwise resistant Gram-negative organisms including Pseudomonas aeruginosa. The charged pyridinum moiety increases water-solubility.

References

1. ^ White NJ (2003). "Melioidosis". Lancet 361: 1715–722. doi:10.1016/S0140-6736(03)13374-0. PMID 12767750.