CHEBI:3508 - ceftazidime

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name ceftazidime
ChEBI ID CHEBI:3508
Definition A third-generation cephalosporin antibiotic bearing pyridinium-1-ylmethyl and {[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-{[(2-carboxypropan-2-yl)oxy]imino}acetamido groups at positions 3 and 7, respectively, of the cephem skeleton.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
Formula C22H22N6O7S2
Net Charge 0
Average Mass 546.57600
Monoisotopic Mass 546.099
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
InChIKey ORFOPKXBNMVMKC-DWVKKRMSSA-N
SMILES [H][C@]12SCC(C[n+]3ccccc3)=C(N1C(=O)[C@H]2NC(=O)C(=N/OC(C)(C)C(O)=O)\c1csc(N)n1)C([O-])=O
Roles Classification
Biological Role(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
drug allergen
Any drug which causes the onset of an allergic reaction.
(via cephalosporin )
EC 2.4.1.129 (peptidoglycan glycosyltransferase) inhibitor
An EC 2.4.1.* (hexosyltransferase) inhibitor that interferes with the action of peptidoglycan glycosyltransferase (EC 2.4.1.129).
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via heterocyclic antibiotic )
Application(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
drug allergen
Any drug which causes the onset of an allergic reaction.
(via cephalosporin )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing ceftazidime (CHEBI:3508) has role antibacterial drug (CHEBI:36047)
ceftazidime (CHEBI:3508) has role drug allergen (CHEBI:88188)
ceftazidime (CHEBI:3508) has role EC 2.4.1.129 (peptidoglycan glycosyltransferase) inhibitor (CHEBI:50696)
ceftazidime (CHEBI:3508) is a cephalosporin (CHEBI:23066)
ceftazidime (CHEBI:3508) is a oxime O-ether (CHEBI:36816)
ceftazidime (CHEBI:3508) is conjugate acid of ceftazidime(1−) (CHEBI:53676)
Incoming ceftazidime pentahydrate (CHEBI:3509) has part ceftazidime (CHEBI:3508)
ceftazidime sodium (CHEBI:53675) has part ceftazidime (CHEBI:3508)
ceftazidime(1−) (CHEBI:53676) is conjugate base of ceftazidime (CHEBI:3508)
IUPAC Name
7β-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-{[(2-carboxypropan-2-yl)oxy]imino}acetyl]amino}-3-(pyridinium-1-ylmethyl)-3,4-didehydrocepham-4-carboxylate
INNs Sources
ceftazidima DrugBank
ceftazidime KEGG DRUG
ceftazidimum DrugBank
Synonyms Sources
(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 IUPAC
CAZ KEGG DRUG
Ceftazidime anhydrous ChemIDplus
Database Links Databases
C06889 KEGG COMPOUND
Ceftazidime Wikipedia
D07654 KEGG DRUG
DB00438 DrugBank
DE2921316 Patent
US4258041 Patent
View more database links
Registry Numbers Types Sources
5475149 Beilstein Registry Number Beilstein
5475149 Reaxys Registry Number Reaxys
72558-82-8 CAS Registry Number ChemIDplus
72558-82-8 CAS Registry Number KEGG DRUG
Citations Waiting for Citations Types Sources
11252323 PubMed citation Europe PMC
11284241 PubMed citation Europe PMC
11591698 PubMed citation Europe PMC
11605815 PubMed citation Europe PMC
11815759 PubMed citation Europe PMC
12048030 PubMed citation Europe PMC
12120880 PubMed citation Europe PMC
12523657 PubMed citation Europe PMC
12767750 PubMed citation Europe PMC
12833570 PubMed citation Europe PMC
1384868 PubMed citation Europe PMC
14961139 PubMed citation Europe PMC
15528892 PubMed citation Europe PMC
15618675 PubMed citation Europe PMC
15687217 PubMed citation Europe PMC
15913752 PubMed citation Europe PMC
16092041 PubMed citation Europe PMC
16501927 PubMed citation Europe PMC
16956383 PubMed citation Europe PMC
18611568 PubMed citation Europe PMC
18926104 PubMed citation Europe PMC
19810175 PubMed citation Europe PMC
1991925 PubMed citation Europe PMC
2068466 PubMed citation Europe PMC
24089577 PubMed citation Europe PMC
2570956 PubMed citation Europe PMC
28543395 PubMed citation Europe PMC
Last Modified
06 March 2018