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targets (9) transporters (4)
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Identification
Name Ceftazidime
Accession Number DB00438 (APRD00857)
Type small molecule
Groups approved
Description

Semisynthetic, broad-spectrum antibacterial derived from cephaloridine and used especially for Pseudomonas and other gram-negative infections in debilitated patients. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Brand names
  • Ceftazidima [INN-Spanish]
  • Ceftazidime pentahydrate
  • Ceftazidime Sodium In Plastic Container
  • Ceftazidimum [INN-Latin]
  • Ceptaz
  • Fortaz
  • Fortaz In Plastic Container
  • Pentacef
  • Tazicef
  • Tazidime
  • Tazidime In Plastic Container
Brand name mixtures Not Available
Categories
  • Anti-Bacterial Agents
  • Cephalosporins
CAS number 78439-06-2
Weight Average: 546.576
Monoisotopic: 546.099138468
Chemical Formula C22H22N6O7S2
InChI Key InChIKey=ORFOPKXBNMVMKC-DWVKKRMSSA-N
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
Plain Text
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
SMILES
[H][C@]12SCC(C[N+]3=CC=CC=C3)=C(N1C(=O)[C@H]2NC(=O)C(=N/OC(C)(C)C(O)=O)\C1=CSC(N)=N1)C([O-])=O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Carboxylic Acids and Derivatives
  • Pyridines and Derivatives
  • Cephalosporins
Substructures
  • Hydroxy Compounds
  • Anions
  • Acetates
  • Amino Ketones
  • Carboxylic Acids and Derivatives
  • Oximes and Derivatives
  • Pyridines and Derivatives
  • Short-chain Hydroxy Acids
  • Aliphatic and Aryl Amines
  • Beta Lactams
  • Enamines
  • Thiazoles
  • Heterocyclic compounds
  • Aromatic compounds
  • Carboxamides and Derivatives
  • Cephalosporins
  • Amino Acids
  • Lactams
  • Imines
  • Azetidines
  • Cations
Pharmacology
Indication 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).
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.
Mechanism of action The bactericidal activity of ceftazidime results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs).
Absorption The absorption of ceftazidime is directly proportional to the size of the dose.
Volume of distribution Not Available
Protein binding < 10%
Metabolism
Route of elimination The elimination of ceftazidime by the kidneys resulted in high therapeutic concentrations in the urine.
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.
Clearance
  • 115 mL/min
Toxicity Ceftazidime overdosage has occurred in patients with renal failure. Reactions have included seizure activity, encephalopathy, asterixis, neuromuscular excitability, and coma.
Affected organisms
  • Enteric bacteria and other eubacteria
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Acs dobfar spa
  • Aurobindo pharma ltd
  • Wockhardt ltd
  • Glaxosmithkline
  • Hospira inc
  • Eli lilly and co
  • Baxter healthcare corp
Packagers
Dosage forms
Form Route Strength
Powder, for solution Intramuscular
Powder, for solution Intravenous
Prices
Unit description Cost Unit
Fortaz 6 g/vial 150.11 USD vial
Ceftazidime 6 gm vial 97.05 USD vial
Fortaz 6 gm vial 82.8 USD vial
Fortaz 2 g/vial 50.01 USD vial
Tazicef 6 gram vial 29.88 USD vial
Fortaz 2 gm add-vantage vial 28.93 USD vial
Fortaz 2 gm vial 28.45 USD vial
Fortaz 1 g/vial 25.44 USD vial
Ceftazidime 2 gm vial 19.97 USD vial
Fortaz 1 gm add-vantage vial 14.71 USD vial
Fortaz 1 gm vial 14.23 USD vial
Tazicef 2 gram vial 10.66 USD vial
Ceftazidime 1 gm vial 10.46 USD vial
Ceftazidime-sodium carb powder 6.27 USD g
Tazicef 1 gram vial 4.57 USD vial
Fortaz-iso-osmot 2 gm/50 ml 0.62 USD ml
Fortaz-iso-osmotic 1 gm/50 ml 0.34 USD ml
Patents Not Available
Properties
State solid
Melting point Not Available
Experimental Properties
Property Value Source
water solubility 396 mg/L PhysProp
logP -1.60 PhysProp
Predicted Properties
Property Value Source
water solubility 5.73e-03 g/l ALOGPS
logP -1.21 ALOGPS
logP -4.33 ChemAxon Molconvert
logS -5.02 ALOGPS
pKa 3.16 ChemAxon Molconvert
hydrogen acceptor count 10 ChemAxon Molconvert
hydrogen donor count 3 ChemAxon Molconvert
polar surface area 191.22 ChemAxon Molconvert
rotatable bond count 9 ChemAxon Molconvert
refractivity 143.88 ChemAxon Molconvert
polarizability 51.06 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Compound C06889 Link_out
PubChem Compound 5481173 Link_out
PubChem Substance 46506143 Link_out
ChemSpider 4587145 Link_out
ChEBI 3508 Link_out
ChEMBL 3508 Link_out
Therapeutic Targets Database DAP000433 Link_out
PharmGKB PA448861 Link_out
HET CAZ Link_out
Drug Product Database 886963 Link_out
RxList http://www.rxlist.com/cgi/generic2/ceftaz.htm Link_out
Drugs.com http://www.drugs.com/cdi/ceftazidime.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Ceftazidime Link_out
ATC Codes
  • J01DD02
AHFS Codes
  • 08:12.06.12
PDB Entries Not Available
FDA label show (359.7 KB)
MSDS show (28 KB)
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Peptidoglycan synthetase ftsI

Pharmacological action: yes
Actions: inhibitor

Cell wall formation. Essential for the formation of a septum of the murein sacculus. Synthesis of cross-linked peptidoglycan from the lipid intermediates

Organism class: bacterial
UniProt ID: P0AD68 Link_out
Gene: ftsI
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Hayes MV, Orr DC: Mode of action of ceftazidime: affinity for the penicillin-binding proteins of Escherichia coli K12, Pseudomonas aeruginosa and Staphylococcus aureus. J Antimicrob Chemother. 1983 Aug;12(2):119-26. Pubmed

2. Penicillin-binding protein 3

Pharmacological action: yes
Actions: inhibitor
UniProt ID: Q75Y35 Link_out
Gene: pbp3
SNPs: SNPJam Report Link_out

References:
  1. Hayes MV, Orr DC: Mode of action of ceftazidime: affinity for the penicillin-binding proteins of Escherichia coli K12, Pseudomonas aeruginosa and Staphylococcus aureus. J Antimicrob Chemother. 1983 Aug;12(2):119-26. Pubmed

3. Penicillin-binding protein 1A

Pharmacological action: yes
Actions: inhibitor

Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan strands) and a penicillin-sensitive transpeptidase C-terminal domain (cross-linking of the peptide subunits)

Organism class: bacterial
UniProt ID: P02918 Link_out
Gene: mrcA
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Hayes MV, Orr DC: Mode of action of ceftazidime: affinity for the penicillin-binding proteins of Escherichia coli K12, Pseudomonas aeruginosa and Staphylococcus aureus. J Antimicrob Chemother. 1983 Aug;12(2):119-26. Pubmed

4. Penicillin-binding protein 1A

Pharmacological action: yes
Actions: inhibitor

Cell wall formation

Organism class: bacterial
UniProt ID: Q8DR59 Link_out
Gene: pbpA Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Hayes MV, Orr DC: Mode of action of ceftazidime: affinity for the penicillin-binding proteins of Escherichia coli K12, Pseudomonas aeruginosa and Staphylococcus aureus. J Antimicrob Chemother. 1983 Aug;12(2):119-26. Pubmed

5. Penicillin-binding protein 1B

Pharmacological action: yes
Actions: inhibitor

Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan strands) and a penicillin-sensitive transpeptidase C-terminal domain (cross-linking of the peptide subunits)

Organism class: bacterial
UniProt ID: P02919 Link_out
Gene: mrcB
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Hayes MV, Orr DC: Mode of action of ceftazidime: affinity for the penicillin-binding proteins of Escherichia coli K12, Pseudomonas aeruginosa and Staphylococcus aureus. J Antimicrob Chemother. 1983 Aug;12(2):119-26. Pubmed

6. Penicillin-binding protein 1B

Pharmacological action: yes
Actions: inhibitor
Organism class: bacterial
UniProt ID: Q9X6W0 Link_out
Gene: ponB Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Hayes MV, Orr DC: Mode of action of ceftazidime: affinity for the penicillin-binding proteins of Escherichia coli K12, Pseudomonas aeruginosa and Staphylococcus aureus. J Antimicrob Chemother. 1983 Aug;12(2):119-26. Pubmed

7. Penicillin-binding protein 2

Pharmacological action: yes
Actions: inhibitor
UniProt ID: Q9X6V3 Link_out
Gene: pbpA
SNPs: SNPJam Report Link_out

References:
  1. Hayes MV, Orr DC: Mode of action of ceftazidime: affinity for the penicillin-binding proteins of Escherichia coli K12, Pseudomonas aeruginosa and Staphylococcus aureus. J Antimicrob Chemother. 1983 Aug;12(2):119-26. Pubmed

8. Penicillin-binding protein 2

Pharmacological action: yes
Actions: inhibitor

Cell wall formation; PBP-2 is responsible for the determination of the rod shape of the cell. Its synthesize cross- linked peptidoglycan from the lipid intermediates

Organism class: bacterial
UniProt ID: P0AD65 Link_out
Gene: mrdA Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Hayes MV, Orr DC: Mode of action of ceftazidime: affinity for the penicillin-binding proteins of Escherichia coli K12, Pseudomonas aeruginosa and Staphylococcus aureus. J Antimicrob Chemother. 1983 Aug;12(2):119-26. Pubmed

9. D-alanyl-D-alanine endopeptidase

Pharmacological action: no
Actions: inhibitor
UniProt ID: P72161 Link_out
Gene: pbpG
SNPs: SNPJam Report Link_out

References:
  1. Hayes MV, Orr DC: Mode of action of ceftazidime: affinity for the penicillin-binding proteins of Escherichia coli K12, Pseudomonas aeruginosa and Staphylococcus aureus. J Antimicrob Chemother. 1983 Aug;12(2):119-26. Pubmed
Transporters

1. Organic cation/carnitine transporter 2

Actions: inhibitor

Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also Relative uptake activity ratio of carnitine to TEA is 11.3

UniProt ID: O76082 Link_out
Gene: SLC22A5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Ganapathy ME, Huang W, Rajan DP, Carter AL, Sugawara M, Iseki K, Leibach FH, Ganapathy V: beta-lactam antibiotics as substrates for OCTN2, an organic cation/carnitine transporter. J Biol Chem. 2000 Jan 21;275(3):1699-707. Pubmed

2. Oligopeptide transporter, small intestine isoform

Actions: inhibitor

Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products

UniProt ID: P46059 Link_out
Gene: SLC15A1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Ganapathy ME, Huang W, Rajan DP, Carter AL, Sugawara M, Iseki K, Leibach FH, Ganapathy V: beta-lactam antibiotics as substrates for OCTN2, an organic cation/carnitine transporter. J Biol Chem. 2000 Jan 21;275(3):1699-707. Pubmed
  2. Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. Pubmed

3. Oligopeptide transporter, kidney isoform

Actions: inhibitor

Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides

UniProt ID: Q16348 Link_out
Gene: SLC15A2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Ganapathy ME, Huang W, Rajan DP, Carter AL, Sugawara M, Iseki K, Leibach FH, Ganapathy V: beta-lactam antibiotics as substrates for OCTN2, an organic cation/carnitine transporter. J Biol Chem. 2000 Jan 21;275(3):1699-707. Pubmed
  2. Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. Pubmed

4. Solute carrier family 22 member 6

Actions: inhibitor
UniProt ID: Q4U2R8 Link_out
Gene: hROAT1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Jariyawat S, Sekine T, Takeda M, Apiwattanakul N, Kanai Y, Sophasan S, Endou H: The interaction and transport of beta-lactam antibiotics with the cloned rat renal organic anion transporter 1. J Pharmacol Exp Ther. 1999 Aug;290(2):672-7. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on April 19, 2011 15:03

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.