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Ceftazidime

Clinical data
Trade names	Fortaz, Tazicef
AHFS/Drugs.com	Monograph
MedlinePlus	a686007
Pregnancy category	AU: B1
Routes of administration	Intravenous, intramuscular
ATC code	J01DD02 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) US: WARNING
Pharmacokinetic data
Bioavailability	91% (IM)
Metabolism	negligible
Elimination half-life	1.6–2 hours
Excretion	90–96% renal
Identifiers
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 oct-2-ene-2-carboxylate
CAS Number	72558-82-8
PubChem CID	5481173
DrugBank	DB00438
ChemSpider	4587145
UNII	DZR1ENT301
ChEBI	CHEBI:3508
CompTox Dashboard (EPA)	DTXSID5022770
ECHA InfoCard	100.069.720
Chemical and physical data
Formula	C22H22N6O7S2
Molar mass	546.58 g/mol g·mol
3D model (JSmol)	Interactive image
SMILES O=C2N1/C(=C(\CS12NC(=O)C(=NOC(C(=O)O)(C)C)c3nc(sc3)N)C4ccccc4)C()=O
InChI InChI=1S/C22H22N6O7S2/c1-22(2,20(33)34)35-26-13(12-10-37-21(23)24-12)16(29)25-14-17(30)28-15(19(31)32)11(9-36-18(14)28)8-27-6-4-3-5-7-27/h3-7,10,14,18H,8-9H2,1-2H3,(H4-,23,24,25,29,31,32,33,34)/b26-13-/t14-,18-/m1/s1 Key:ORFOPKXBNMVMKC-DWVKKRMSSA-N
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Ceftazidime (INN) (/sɛfˈtæzdiːm/) 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.

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.

Ceftazidine is first line treatment for the rare tropical infection, melioidosis.

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. "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
2. White NJ (2003). "Melioidosis". Lancet. 361 (9370): 1715–722. doi:10.1016/S0140-6736(03)13374-0. PMID 12767750.

• Ill-formatted IPAc-en transclusions
• Cephalosporin antibiotics
• Thiazoles
• Pyridines
• Zwitterions