CHEBI:3545 - cephapirin sodium

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ChEBI Name cephapirin sodium
ChEBI ID CHEBI:3545
Definition The sodium salt of cephapirin. A first-generation cephalosporin antibiotic, it is effective against gram-negative and gram-positive organisms. Being more resistant to β-lactamases than penicillins, it is effective agains most staphylococci, though not methicillin-resistant staphylococci.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C17H16N3NaO6S2
Net Charge 0
Average Mass 445.44500
Monoisotopic Mass 445.03782
InChI InChI=1S/C17H17N3O6S2.Na/c1-9(21)26-6-10-7-28-16-13(15(23)20(16)14(10)17(24)25)19-12(22)8-27-11-2-4-18-5-3-11;/h2-5,13,16H,6-8H2,1H3,(H,19,22)(H,24,25);/q;+1/p-1/t13-,16-;/m1./s1
InChIKey VGEOUKPOQQEQSX-OALZAMAHSA-M
SMILES [Na+].[H][C@]12SCC(COC(C)=O)=C(N1C(=O)[C@H]2NC(=O)CSc1ccncc1)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 )
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 cephapirin sodium (CHEBI:3545) has part cephapirin(1−) (CHEBI:59217)
cephapirin sodium (CHEBI:3545) has role antibacterial drug (CHEBI:36047)
cephapirin sodium (CHEBI:3545) is a cephalosporin (CHEBI:23066)
cephapirin sodium (CHEBI:3545) is a organic sodium salt (CHEBI:38700)
IUPAC Name
sodium (6R,7R)-3-[(acetyloxy)methyl]-8-oxo-7-{[(pyridin-4-ylsulfanyl)acetyl]amino}-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
Synonyms Sources
Cefapirin sodium KEGG COMPOUND
Cephapirin sodium KEGG COMPOUND
monosodium (6R,7R)-3-(hydroxymethyl)-8-oxo-7-(2-(4-pyridylthio)acetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate acetate ChemIDplus
sodium 7-(pyrid-4-ylthioacetamido)cephalosporanate ChEBI
Sodium cefapirin KEGG COMPOUND
Manual Xrefs Databases
C08101 KEGG COMPOUND
D00908 KEGG DRUG
DB01139 DrugBank
US3422100 Patent
US3503967 Patent
US3578661 Patent
View more database links
Registry Numbers Types Sources
24356-60-3 CAS Registry Number ChemIDplus
4900637 Beilstein Registry Number Beilstein
Last Modified
04 May 2010