CHEBI:59213 - cefpiramide

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ChEBI Name cefpiramide
ChEBI ID CHEBI:59213
Definition A third-generation cephalosporin antibiotic with [(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl and (R)-2-{[(4-hydroxy-6-methylpyridin-3-yl)carbonyl]amino}-2-(4-hydroxyphenyl)acetamido groups at positions 3 and 7, respectively, of the cephem skeleton. It has a broad spectrum of antibacterial activity.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C25H24N8O7S2
Net Charge 0
Average Mass 612.63700
Monoisotopic Mass 612.121
InChI InChI=1S/C25H24N8O7S2/c1-11-7-16(35)15(8-26-11)20(36)27-17(12-3-5-14(34)6-4-12)21(37)28-18-22(38)33-19(24(39)40)13(9-41-23(18)33)10-42-25-29-30-31-32(25)2/h3-8,17-18,23,34H,9-10H2,1-2H3,(H,26,35)(H,27,36)(H,28,37)(H,39,40)/t17-,18-,23-/m1/s1
InChIKey PWAUCHMQEXVFJR-PMAPCBKXSA-N
SMILES [H][C@]12SCC(CSc3nnnn3C)=C(N1C(=O)[C@@]2([H])NC(=O)[C@H](NC(=O)c1cnc(C)cc1O)c1ccc(O)cc1)C(O)=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
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 cefpiramide (CHEBI:59213) has role antibacterial drug (CHEBI:36047)
cefpiramide (CHEBI:59213) is a carboxylic acid (CHEBI:33575)
cefpiramide (CHEBI:59213) is a cephalosporin (CHEBI:23066)
cefpiramide (CHEBI:59213) is conjugate acid of cefpiramide(1−) (CHEBI:59214)
Incoming cefpiramide(1−) (CHEBI:59214) is conjugate base of cefpiramide (CHEBI:59213)
IUPAC Names
(6R,7R)-7-{[(2R)-2-{[(4-hydroxy-6-methylpyridin-3-yl)carbonyl]amino}-2-(4-hydroxyphenyl)acetyl]amino}-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
7β-[(2R)-2-{[(4-hydroxy-6-methylpyridin-3-yl)carbonyl]amino}-2-(4-hydroxyphenyl)acetamido]-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}-3,4-didehydrocepham-4-carboxylic acid
INNs Sources
cefpiramide ChemIDplus
cefpiramido ChemIDplus
cefpiramidum ChemIDplus
Manual Xrefs Databases
552 DrugCentral
BE833063 Patent
Cefpiramide Wikipedia
D03428 KEGG DRUG
DB00430 DrugBank
US4156724 Patent
US4160087 Patent
View more database links
Registry Numbers Types Sources
70797-11-4 CAS Registry Number ChemIDplus
8179314 Beilstein Registry Number Beilstein
Citation Waiting for Citations Type Source
29017833 PubMed citation Europe PMC
Last Modified
13 February 2018