CHEBI:474053 - cefazolin

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ChEBI Name cefazolin
ChEBI ID CHEBI:474053
Definition A first-generation cephalosporin compound having [(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl and (1H-tetrazol-1-ylacetyl)amino side-groups at positions 3 and 7 respectively.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:3482
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Formula C14H14N8O4S3
Net Charge 0
Average Mass 454.511
Monoisotopic Mass 454.030
InChI InChI=1S/C14H14N8O4S3/c1-6-17-18-14(29-6)28-4-7-3-27-12-9(11(24)22(12)10(7)13(25)26)16-8(23)2-21-5-15-19-20-21/h5,9,12H,2-4H2,1H3,(H,16,23)(H,25,26)/t9-,12-/m1/s1
InChIKey MLYYVTUWGNIJIB-BXKDBHETSA-N
SMILES [C@]12(N(C(=C(CS1)CSC3=NN=C(S3)C)C(=O)O)C([C@H]2NC(=O)CN4C=NN=N4)=O)[H]
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 )
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 cefazolin (CHEBI:474053) has role antibacterial drug (CHEBI:36047)
cefazolin (CHEBI:474053) is a cephalosporin (CHEBI:23066)
cefazolin (CHEBI:474053) is a tetrazoles (CHEBI:35689)
cefazolin (CHEBI:474053) is a thiadiazoles (CHEBI:38099)
cefazolin (CHEBI:474053) is conjugate acid of cefazolin(1−) (CHEBI:53657)
Incoming cefazolin(1−) (CHEBI:53657) is conjugate base of cefazolin (CHEBI:474053)
IUPAC Name
3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-7β-[(1H-tetrazol-1-ylacetyl)amino]-3,4-didehydrocepham-4-carboxylic acid
INNs Sources
cefazolin ChemIDplus
cefazolina ChemIDplus
cefazoline ChemIDplus
cefazolinum ChemIDplus
Synonyms Sources
(6R,7R)-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-7-[(1H-tetrazol-1-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid IUPAC
Cefamezin ChemIDplus
Cephamezine ChemIDplus
Cephazolidin ChemIDplus
Cephazolin ChemIDplus
Cephazoline ChemIDplus
CEZ ChEBI
Manual Xrefs Databases
1910 VSDB
530 DrugCentral
C06880 KEGG COMPOUND
Cefazolin Wikipedia
D02299 KEGG DRUG
DB01327 DrugBank
HMDB0015422 HMDB
LSM-34744 LINCS
US3516997 Patent
View more database links
Registry Numbers Types Sources
25953-19-9 CAS Registry Number KEGG COMPOUND
25953-19-9 CAS Registry Number DrugBank
25953-19-9 CAS Registry Number KEGG DRUG
25953-19-9 CAS Registry Number ChemIDplus
4169371 Beilstein Registry Number Beilstein
4169371 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
12569987 PubMed citation Europe PMC
2083978 PubMed citation Europe PMC
22011388 PubMed citation Europe PMC
23702270 PubMed citation Europe PMC
24462449 PubMed citation Europe PMC
28543395 PubMed citation Europe PMC
29017833 PubMed citation Europe PMC
6176550 PubMed citation Europe PMC
Last Modified
14 March 2018