CHEBI:554446 - cephapirin

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ChEBI Name cephapirin
ChEBI ID CHEBI:554446
Definition A cephalosporin with acetoxymethyl and 2(pyridin-4-ylsulfanyl)acetamido substituents at positions 3 and 7, respectively, of the cephem skeleton. It is used (as its sodium salt) as an antibiotic, being effective against gram-negative and gram-positive organisms.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:3544
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Formula C17H17N3O6S2
Net Charge 0
Average Mass 423.46300
Monoisotopic Mass 423.056
InChI InChI=1S/C17H17N3O6S2/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)/t13-,16-/m1/s1
InChIKey UQLLWWBDSUHNEB-CZUORRHYSA-N
SMILES [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 )
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ChEBI Ontology
Outgoing cephapirin (CHEBI:554446) has role antibacterial drug (CHEBI:36047)
cephapirin (CHEBI:554446) is a cephalosporin (CHEBI:23066)
cephapirin (CHEBI:554446) is conjugate acid of cephapirin(1−) (CHEBI:59217)
Incoming cephapirin(1−) (CHEBI:59217) is conjugate base of cephapirin (CHEBI:554446)
IUPAC Name
(6R,7R)-3-acetoxymethyl-7-[(pyridin-4-ylsulfanyl)acetamido]-3,4-didehydrocepham-4-carboxylic acid
INNs Sources
cefapirin ChemIDplus
cefapirina DrugBank
cefapirine DrugBank
cefapirinum DrugBank
Synonyms Sources
(6R,7R)-3-(acetoxymethyl)-8-oxo-7-{[(pyridin-4-ylsulfanyl)acetyl]amino}-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid ChEBI
Cefaprin DrugBank
Cephapirine DrugBank
CEPR KEGG DRUG
Database Links Databases
575 DrugCentral
C06896 KEGG COMPOUND
Cephapirin Wikipedia
D07636 KEGG DRUG
DB01139 DrugBank
HMDB0015270 HMDB
HMDB0030451 HMDB
View more database links
Registry Numbers Types Sources
21593-23-7 CAS Registry Number KEGG COMPOUND
21593-23-7 CAS Registry Number ChemIDplus
4031966 Reaxys Registry Number Reaxys
4031996 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
19246140 PubMed citation Europe PMC
2083978 PubMed citation Europe PMC
23948762 PubMed citation Europe PMC
24224523 PubMed citation Europe PMC
29017833 PubMed citation Europe PMC
Last Modified
14 March 2018