Ceftazidime (CHEM043564)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-06-03 11:03:25 UTC
Update Date2016-11-09 01:22:56 UTC
Accession NumberCHEM043564
Identification
Common NameCeftazidime
ClassSmall Molecule
DescriptionSemisynthetic, broad-spectrum antibacterial derived from cephaloridine and used especially for Pseudomonas and other gram-negative infections in debilitated patients.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
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
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot 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
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fb9-9681160000-8d070b22df5da67959c7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0076-9412121000-eb6fcb1d7bff5b5740d8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("Ceftazidime,1TMS,#1" TMS) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0udi-1900000000-35c537be0b49e8347500Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0udi-3900000000-f8108350d09aeabb208fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0pb9-9600000000-3a117de626550cd6bd1eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4i-9200000000-42d1f87964b083915995Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4i-9100000000-9b08b7904165504611b6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014j-0115900000-d76de6ad1809c0528b8cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0006-1910000000-cb7ea1c7b4b139a7336eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-01tl-3900000000-07fadc61e1b566ec14baSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-004i-5900000000-e92b85ec9fabd9a4c1feSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-004i-7900000000-548213f534e499ba783bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-0006-1910000000-65431915e349356c7c1bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-014j-0115900000-9ad2a534e640ea11a3edSpectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-0udi-1900000000-4950d2132b208ec5d384Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0udi-3900000000-14f37c649573c40395a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-3000090000-ddd9d3e45c1a4a2b2fe1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udj-3003090000-b9d509184493350fa947Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0076-9000000000-07cddb7d4d0578489549Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1000090000-1e425f398c7593cf9579Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-3000390000-5eb1fef4c62c4bd6f76aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-416ed39c2b7232bc4815Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000b-0040190000-ef35cf4bfec6d17b0420Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-5390760000-4fe00424f5859481cc67Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9311110000-ac11f8fa881f684bcd4aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000900000-1e6315ac62adbda9f59aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a59-1102900000-7b724201fe64e25739d7Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
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