Ceftazidime

Synonyms :
(6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-{[(2-carboxypropan-2-yl)oxy]imino}acetyl]amino}-8-oxo-3-(pyridinium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate, CAZ, Ceftazidim, Ceftazidima, Ceftazidime, Ceftazidime anhydrous, Ceftazidimum

Status : approved

Category

Anti-Bacterial Agents

Therapeutic Classification

OTHER BETA-LACTAM ANTIBACTERIALS

ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
OTHER BETA-LACTAM ANTIBACTERIALS
Cephalosporins

Description

Semisynthetic, broad-spectrum antibacterial derived from cephaloridine and used especially for Pseudomonas and other gram-negative infections in debilitated patients. [PubChem]

Used

For the treatment of patients with infections caused by susceptible strains of organisms in the following diseases: lower respiratory tract infections,skin and skin structure infections, urinary tract infections, bacterial septicemia, bone and joint infections, gynecologic infections, intra abdominal infections (including peritonitis), and central nervous system infections (including meningitis).

Mechanism Of Action

The bactericidal activity of ceftazidime results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs).

Dosage

Form Route Strength
Injection, powder, for solution intramuscular; intravenous 1 g/20mL
Injection, powder, for solution intravenous 2 g
Injection, powder, for solution intravenous 2 g/20mL
Injection, powder, for solution intravenous 200 mg/mL
Injection, powder, for solution intravenous 6 g/100mL
Injection, powder, for solution intravenous 6 g/30mL
Injection, solution intravenous 1 g/50mL
Injection, solution intravenous 2 g/50mL
Powder for solution intravenous 3 g
Powder for solution intramuscular; intravenous 1 g
Powder for solution intravenous 2 g
Powder for solution intravenous 6 g
Powder for solution intravenous 10 g
Injection, powder, for solution intramuscular; intravenous 100 mg/mL
Injection, powder, for solution intramuscular; intravenous 111 mg/mL
Injection, powder, for solution intramuscular; intravenous 170 mg/mL
Injection, powder, for solution intramuscular; intravenous 200 mg/mL
Injection, powder, for solution intramuscular; intravenous 56 mg/mL
Injection, powder, lyophilized, for solution intramuscular; intravenous 20 mg/mL
Injection, solution intravenous 20 mg/mL
Injection, solution intravenous 40 mg/mL
Powder for solution intramuscular; intravenous 500 mg
Injection, powder, for solution intramuscular; intravenous 1 g
Injection, powder, for solution intramuscular; intravenous 2 g
Injection, powder, for solution intravenous 20 mg/mL
Injection, powder, for solution intravenous 40 mg/mL
Injection, powder, for solution intravenous 6 g
Powder for solution intravenous 1 g
Powder intramuscular; intravenous 500 mg

Pharmacodynamics

Ceftazidime is a semisynthetic, broad-spectrum, beta-lactam antibiotic for parenteral administration. Ceftazidime is bactericidal in action exerting its effect by inhibition of enzymes responsible for cell-wall synthesis, primarily penicillin binding protein 3 (PBP3). A wide range of gram-negative organisms is susceptible to ceftazidime in vitro, including strains resistant to gentamicin and other aminoglycosides. In addition, ceftazidime has been shown to be active against gram-positive organisms. It is highly stable to most clinically important beta-lactamases, plasmid or chromosomal, which are produced by both gram-negative and gram-positive organisms and, consequently, is active against many strains resistant to ampicillin and other cephalosporins. Ceftazidime has activity against the gram-negative organisms Pseudomonas and Enterobacteriaceae. Its activity against Pseudomonas is a distinguishing feature of ceftazidime among the cephalosporins.

Toxic Effect

Ceftazidime overdosage has occurred in patients with renal failure. Reactions have included seizure activity, encephalopathy, asterixis, neuromuscular excitability, and coma.

Absorption

The absorption of ceftazidime is directly proportional to the size of the dose.

Half Life

Half-life, following IV administration, is approximately 1.9-hours. Since ceftazidime is eliminated almost solely by the kidneys, its serum half-life is significantly prolonged in patients with impaired renal function.

Protein Binding

< 10%

Elimination Route

The elimination of ceftazidime by the kidneys resulted in high therapeutic concentrations in the urine.

Clearance

* 115 mL/min

Chemical Classification

This compound belongs to the class of organic compounds known as cephalosporins. These are compounds containing a 1,2-thiazine fused to a 2-azetidinone to for a oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid moiety or a derivative thereof.

Cephalosporins

Organic compounds

Organoheterocyclic compounds

Lactams

Beta lactams

Salt : Ceftazidime pentahydrate

Chemical Name

(6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-{[(2-carboxypropan-2-yl)oxy]imino}acetyl]amino}-8-oxo-3-(pyridinium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Brands

name Dosage form Country
Ceftazidime injection, powder, for solution US
Ceftazidime injection, powder, for solution US
Ceftazidime injection, powder, for solution US
Ceftazidime injection, powder, for solution US
Ceftazidime injection, powder, for solution US
Ceftazidime injection, powder, for solution US
Ceftazidime injection, powder, for solution US
Ceftazidime injection, powder, for solution US
Ceftazidime injection, powder, for solution US
Ceftazidime injection, powder, for solution US
Ceftazidime injection, powder, for solution US
Ceftazidime injection, powder, for solution US
Ceftazidime and Dextrose injection, solution US
Ceftazidime and Dextrose injection, solution US
Ceftazidime for Injection BP powder for solution Canada
Ceftazidime for Injection BP powder for solution Canada
Ceftazidime for Injection BP powder for solution Canada
Ceftazidime for Injection, BP powder for solution Canada
Ceftazidime for Injection, USP powder for solution Canada
Ceftazidime for Injection, USP powder for solution Canada
Ceftazidime for Injection, USP powder for solution Canada
Ceptaz Inj 10gm/vial powder for solution Canada
Ceptaz Inj 1gm/vial powder for solution Canada
Ceptaz Inj 2gm/vial powder for solution Canada
Ceptaz Injection – Pws Im IV 1g/vial powder for solution Canada
Ceptaz Injection – Pws IV 2gm/vial powder for solution Canada
Ceptaz Injection – Pws IV 10gm/vial powder for solution Canada
Fortaz injection, powder, lyophilized, for solution US
Fortaz injection, powder, for solution US
Fortaz injection, powder, for solution US
Fortaz injection, powder, for solution US
Fortaz injection, powder, for solution US
Fortaz injection, solution US
Fortaz injection, solution US
Fortaz injection, powder, for solution US
Fortaz injection, powder, for solution US
Fortaz – Inj 1g/vial powder for solution Canada
Fortaz – Inj 2g/vial powder for solution Canada
Fortaz – Inj 6g/vial powder for solution Canada
Fortaz Inj 1gm/vial powder for solution Canada
Fortaz Inj 2gm/vial powder for solution Canada
Fortaz Inj 500mg/vial powder for solution Canada
Fortaz Pws Inj 6gm/vial powder for solution Canada
Tazicef injection, powder, for solution US
Tazicef injection, powder, for solution US
Tazicef injection, powder, for solution US
Tazicef injection, powder, for solution US
Tazicef injection, powder, for solution US
Tazidime Add-vantage Inj 1.0gm/vial powder for solution Canada
Tazidime Add-vantage Inj 2gm/vial powder for solution Canada
Tazidime Inj 500mg/vial powder Canada

Drug Drug Interactions

  •  Acenocoumarol  : May enhance the anticoagulant effect of Vitamin K Antagonists.
  •  Amikacin  : Cephalosporins (3rd Generation) may enhance the nephrotoxic effect of Aminoglycosides.
  •  Arbekacin  : Cephalosporins (3rd Generation) may enhance the nephrotoxic effect of Aminoglycosides.
  •  Chloramphenicol  : May diminish the therapeutic effect of Ceftazidime.
  •  Framycetin  : Cephalosporins (3rd Generation) may enhance the nephrotoxic effect of Aminoglycosides.
  •  Gentamicin  : Cephalosporins (3rd Generation) may enhance the nephrotoxic effect of Aminoglycosides.
  •  Kanamycin  : Cephalosporins (3rd Generation) may enhance the nephrotoxic effect of Aminoglycosides.
  •  Neomycin  : Cephalosporins (3rd Generation) may enhance the nephrotoxic effect of Aminoglycosides.
  •  Netilmicin  : Cephalosporins (3rd Generation) may enhance the nephrotoxic effect of Aminoglycosides.
  •  Probenecid  : May increase the serum concentration of Cephalosporins.
  •  Ribostamycin  : Cephalosporins (3rd Generation) may enhance the nephrotoxic effect of Aminoglycosides.
  •  Spectinomycin  : Cephalosporins (3rd Generation) may enhance the nephrotoxic effect of Aminoglycosides.
  •  Streptomycin  : Cephalosporins (3rd Generation) may enhance the nephrotoxic effect of Aminoglycosides.
  •  Tobramycin  : Cephalosporins (3rd Generation) may enhance the nephrotoxic effect of Aminoglycosides.
  •  Warfarin  : May enhance the anticoagulant effect of Vitamin K Antagonists.

Calculated Property

kind Value Source
logP -1.2 ALOGPS
logS -5 ALOGPS
Water Solubility 5.73e-03 g/l ALOGPS
logP -4.1 ChemAxon
IUPAC Name 1-{[(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(1-carboxy-1-methylethoxy)imino]acetamido]-2-carboxylato-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}pyridin-1-ium ChemAxon
Traditional IUPAC Name ceftazidime ChemAxon
Molecular Weight 546.576 ChemAxon
Monoisotopic Weight 546.099138468 ChemAxon
SMILES [O-]C(=O)C1=C(CS[C@]2([H])[C@H](NC(=O)C(=N/OC(C)(C)C(O)=O)C3=CSC(N)=N3)C(=O)N12)C[N+]1=CC=CC=C1 ChemAxon
Molecular Formula C22H22N6O7S2 ChemAxon
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 ChemAxon
InChIKey InChIKey=ORFOPKXBNMVMKC-DWVKKRMSSA-N ChemAxon
Polar Surface Area (PSA) 191.22 ChemAxon
Refractivity 143.88 ChemAxon
Polarizability 51.06 ChemAxon
Rotatable Bond Count 9 ChemAxon
H Bond Acceptor Count 10 ChemAxon
H Bond Donor Count 3 ChemAxon
pKa (strongest acidic) 2.77 ChemAxon
pKa (strongest basic) 4.26 ChemAxon
Physiological Charge -1 ChemAxon
Number of Rings 4 ChemAxon
Bioavailability 1 ChemAxon
Rule of Five 0 ChemAxon
Ghose Filter 0 ChemAxon
MDDR-Like Rule 1 ChemAxon

Affected organism

Enteric bacteria and other eubacteria

Target within organism

  • Peptidoglycan synthase FtsI : in Escherichia coli (strain K12)
  • Penicillin-binding protein 3 : in Streptococcus pneumoniae
  • Penicillin-binding protein 1A : in Escherichia coli (strain K12)
  • Penicillin-binding protein 1A : in Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
  • Penicillin-binding protein 1B : in Escherichia coli (strain K12)
  • Penicillin-binding protein 1B : in Pseudomonas aeruginosa
  • Penicillin-binding protein 2 : in Pseudomonas aeruginosa
  • Penicillin-binding protein 2 : in Escherichia coli (strain K12)
  • D-alanyl-D-alanine endopeptidase : in Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)