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CHEBI:59213 - cefpiramide

ChEBI IDCHEBI:59213
ChEBI Namecefpiramide
Stars
DefinitionA 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.
Last Modified13 February 2018
SubmitterGareth Owen
DownloadsMolfile
FormulaC25H24N8O7S2
Net Charge0
Average Mass612.650
Monoisotopic Mass612.12094
SMILES[H][C@]12SCC(CSc3nnnn3C)=C(C(=O)O)N1C(=O)[C@@]2([H])NC(=O)[C@H](NC(=O)c1cnc(C)cc1O)c1ccc(O)cc1
InChIInChI=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
InChIKeyPWAUCHMQEXVFJR-PMAPCBKXSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
antibacterial drug  A drug used to treat or prevent bacterial infections.
drug allergen  Any drug which causes the onset of an allergic reaction.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
Applications:
antibacterial drug  A drug used to treat or prevent bacterial infections.
drug allergen  Any drug which causes the onset of an allergic reaction.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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  Source
cefpiramideChemIDplus
cefpiramidoChemIDplus
cefpiramidumChemIDplus
Manual XrefsDatabases
DB00430DrugBank
BE833063Patent
US4156724Patent
US4160087Patent
D03428KEGG DRUG
CefpiramideWikipedia
552DrugCentral
Registry NumbersSources
Beilstein:8179314Beilstein
CAS:70797-11-4ChemIDplus
Citations