Ceftazidime (CED0001428)

Record Information
Version1.0
Creation Date2016-06-03 11:03:25 UTC
Update Date2026-05-14 16:38:45 UTC
Accession NumberCHEM043564
Identification
Common NameCeftazidime
ClassSmall Molecule
Description
Ceftazidime is an organoheterocyclic compound with the chemical formula C22H22N6O7S2. Ceftazidime belongs to the beta lactams, a subclass of lactams within the organic compounds. With an average molecular weight of 546.58 g/mol, Ceftazidime is a heavy molecule. The compound is found in or released from three recorded sources, including antennas from electrical and electronic equipment, as well as antibiotics and beta-lactam antibacterials from pharmaceuticals, veterinary products, and healthcare. Exposure routes for the substance include oral, intravenous, intramuscular, and inhalation. Ceftazidime interacts with five recorded protein targets. It serves as an inhibitor or substrate for Penicillin-binding protein 1A (mrcA), Penicillin-binding protein 1B (mrcB), Peptidoglycan D,D-transpeptidase FtsI (ftsI), and Peptidoglycan D,D-transpeptidase MrdA (mrdA), in addition to one other protein.
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(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-carboxylateChEBI
CAZChEBI
CeftazidimaChEBI
Ceftazidime anhydrousChEBI
CeftazidimumChEBI
CeptazKegg
FortazKegg
(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-carboxylic acidGenerator
Pentahydrate, ceftazidimeHMDB
FortumHMDB
Anhydrous, ceftazidimeHMDB
Ceftazidime pentahydrateHMDB
TazidimeHMDB
Chemical FormulaC22H22N6O7S2
Average Molecular Mass546.576 g/mol
Monoisotopic Mass546.099 g/mol
CAS Registry Number72558-82-8
IUPAC Name1-{[(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
Traditional Nameceftazidime
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
InChI IdentifierInChI=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
InChI KeyORFOPKXBNMVMKC-DWVKKRMSSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cephalosporins. Cephalosporins 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentCephalosporins
Alternative Parents
Substituents
  • Cephalosporin
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • 2,4-disubstituted 1,3-thiazole
  • Meta-thiazine
  • Dicarboxylic acid or derivatives
  • 1,3-thiazol-2-amine
  • Pyridine
  • Pyridinium
  • Azole
  • Heteroaromatic compound
  • Tertiary carboxylic acid amide
  • Thiazole
  • Amino acid or derivatives
  • Azetidine
  • Carboxamide group
  • Carboxylic acid salt
  • Amino acid
  • Secondary carboxylic acid amide
  • Thioether
  • Hemithioaminal
  • Dialkylthioether
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Primary amine
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Organic salt
  • Organonitrogen compound
  • Organic zwitterion
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0057 g/LALOGPS
logP-1.2ALOGPS
logP-4.1ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)2.77ChemAxon
pKa (Strongest Basic)4.26ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area191.22 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity143.88 m³·mol⁻¹ChemAxon
Polarizability51.06 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0fb9-9681160000-8d070b22df5da67959c7Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0076-9412121000-eb6fcb1d7bff5b5740d8Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-1900000000-35c537be0b49e8347500Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-3900000000-f8108350d09aeabb208fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0pb9-9600000000-3a117de626550cd6bd1eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9200000000-42d1f87964b083915995Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9100000000-9b08b7904165504611b6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014j-0115900000-d76de6ad1809c0528b8cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-1910000000-cb7ea1c7b4b139a7336eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01tl-3900000000-07fadc61e1b566ec14baNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-5900000000-e92b85ec9fabd9a4c1feNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-7900000000-548213f534e499ba783bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-1910000000-65431915e349356c7c1bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014j-0115900000-9ad2a534e640ea11a3edNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-1900000000-4950d2132b208ec5d384Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-3900000000-14f37c649573c40395a9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-3000090000-ddd9d3e45c1a4a2b2fe1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udj-3003090000-b9d509184493350fa947Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0076-9000000000-07cddb7d4d0578489549Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-1000090000-1e425f398c7593cf9579Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-3000390000-5eb1fef4c62c4bd6f76aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4l-9000000000-416ed39c2b7232bc4815Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000b-0040190000-ef35cf4bfec6d17b0420Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000l-5390760000-4fe00424f5859481cc67Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9311110000-ac11f8fa881f684bcd4aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0000900000-1e6315ac62adbda9f59aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a59-1102900000-7b724201fe64e25739d7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-055e-9211500000-a3b366041cb7bf9c5266Not AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
5599.0Log mg/kg[3100:10000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
306AntibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
341Beta-lactam antibacterialsHealthcare, pharmaceuticals & veterinary productsNot Available
506AntennasElectrical & Electronic EquipmentNot Available
Pathways
1 pathway
Ceftazidime Drug Metabolism Action Pathway
Ceftazidime Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Penicillin-binding protein 1A structureClick to view 3D structurePenicillin-binding protein 1AQ07806Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)Predicted (SEA)0.233548
Click to view 3D structureSHV-5 extended spectrum beta-lactamaseQ6REX6Escherichia coliPredicted (SEA)0.155698
Click to view 3D structureSolute carrier family 22 member 6Q4U2R8HumansPredicted (SEA)0.155698
Click to view 3D structureOrganic anion transporter 3Q8TCC7HumansPredicted (SEA)0.155698
Solute carrier family 22 member 11 structureClick to view 3D structureSolute carrier family 22 member 11Q9NSA0HumansPredicted (SEA)0.0778492
Click to view 3D structureBeta-lactamaseB2ZTR6Acinetobacter baumanniiPredicted (SEA)0.155698
Click to view 3D structureADC-11D6NSM8Acinetobacter baumanniiPredicted (SEA)0.155698
Click to view 3D structureAmpCQ83TT7Escherichia coliPredicted (SEA)0.155698
Peptidoglycan D,D-transpeptidase FtsI structureClick to view 3D structurePeptidoglycan D,D-transpeptidase FtsIQ51504Pseudomonas aeruginosaPredicted (SEA)0.233548
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)40.3259
Click to view 3D structureBeta-lactamase ACC-4A4ZYU9Escherichia coliPredicted (SEA)0.0778492
Apoptotic protease-activating factor 1 structureClick to view 3D structureApoptotic protease-activating factor 1O14727HumansPredicted (SEA)20.3965
72 kDa type IV collagenase structureClick to view 3D structure72 kDa type IV collagenaseP08253HumansPredicted (SEA)502.672
Speckle-type POZ protein structureClick to view 3D structureSpeckle-type POZ proteinO43791HumansPredicted (SEA)1.71268
Click to view 3D structureEfflux transporterQ3S5C3Salmonella newportPredicted (SEA)0.544945
Click to view 3D structureClass C beta-lactamase CMY-36Q48435Klebsiella pneumoniaePredicted (SEA)0.544945
26S proteasome non-ATPase regulatory subunit 14 structureClick to view 3D structure26S proteasome non-ATPase regulatory subunit 14O00487HumansPredicted (SEA)25.301
Carboxy-terminal domain RNA polymerase II polypeptide A small phosphatase 1 structureClick to view 3D structureCarboxy-terminal domain RNA polymerase II polypeptide A small phosphatase 1Q9GZU7HumansPredicted (SEA)414.158
Click to view 3D structurePER-2 beta-lactamaseA2RP81Citrobacter freundiiPredicted (SEA)0.544945
Tyrosine-protein phosphatase non-receptor type 11 structureClick to view 3D structureTyrosine-protein phosphatase non-receptor type 11Q06124HumansPredicted (SEA)625.596
Click to view 3D structureSolute carrier family 15 member 2Q63424Rattus norvegicusPredicted (SEA)36.8227
Click to view 3D structureProbable nicotinate-nucleotide adenylyltransferaseP65502Staphylococcus aureus (strain N315)Predicted (SEA)330.626
Nuclear receptor subfamily 1 group I member 2 structureClick to view 3D structureNuclear receptor subfamily 1 group I member 2O75469HumansPredicted (SEA)1035.71
Small ubiquitin-related modifier 1 structureClick to view 3D structureSmall ubiquitin-related modifier 1P63165HumansPredicted (SEA)904.141
Click to view 3D structureBeta-lactamase SHV-1P0AD63Escherichia coliPredicted (SEA)2.02408
Concentrations
Not Available
External Links
DrugBank IDDB00438
HMDB IDHMDB0014582
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCeftazidime
Chemspider ID4587145
ChEBI ID3508
PubChem Compound ID5481173
Kegg Compound IDC06889
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11252323
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11284241
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=11591698
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=11605815
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=11815759
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=12048030
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=12120880
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=12523657
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=12767750
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=12833570
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=1384868
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=14961139
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=15528892
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=15618675
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=15687217
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=15913752
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=16092041
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=16501927
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=16956383
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=18611568
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=18926104
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=19810175
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=1991925
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=2068466
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=24089577
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=2570956
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=28543395