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CHEBI:404903 - ertapenem

ChEBI IDCHEBI:404903
ChEBI Nameertapenem
Stars
DefinitionMeropenem in which the one of the two methyl groups attached to the amide nitrogen is replaced by hydrogen while the other is replaced by a 3-carboxyphenyl group. The sodium salt is used for the treatment of moderate to severe susceptible infections including intra-abdominal and acute gynaecological infections, pneumonia, and infections of the skin and of the urinary tract.
Secondary ChEBI IDCHEBI:471574
Last Modified22 February 2017
DownloadsMolfile
FormulaC22H25N3O7S
Net Charge0
Average Mass475.523
Monoisotopic Mass475.14132
SMILES[H][C@@]1(SC2=C(C(=O)O)N3C(=O)[C@]([H])([C@@H](C)O)[C@@]3([H])[C@H]2C)CN[C@]([H])(C(=O)Nc2cccc(C(=O)O)c2)C1
InChIInChI=1S/C22H25N3O7S/c1-9-16-15(10(2)26)20(28)25(16)17(22(31)32)18(9)33-13-7-14(23-8-13)19(27)24-12-5-3-4-11(6-12)21(29)30/h3-6,9-10,13-16,23,26H,7-8H2,1-2H3,(H,24,27)(H,29,30)(H,31,32)/t9-,10-,13+,14+,15-,16-/m1/s1
InChIKeyJUZNIMUFDBIJCM-ANEDZVCMSA-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.
antibacterial agent  A substance (or active part thereof) that kills or slows the growth of bacteria.
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.
Application:
antibacterial drug  A drug used to treat or prevent bacterial infections.
ChEBI Ontology
Outgoing Relation(s)
ertapenem (CHEBI:404903) has role antibacterial drug (CHEBI:36047)
ertapenem (CHEBI:404903) is a carbapenemcarboxylic acid (CHEBI:46634)
ertapenem (CHEBI:404903) is a pyrrolidinecarboxamide (CHEBI:46770)
ertapenem (CHEBI:404903) is conjugate acid of ertapenem(1−) (CHEBI:60071)
Incoming Relation(s)
ertapenem(1−) (CHEBI:60071) is conjugate base of ertapenem (CHEBI:404903)
IUPAC Name 
(4R,5S,6S)-3-({(3S,5S)-5-[(3-carboxyphenyl)carbamoyl]pyrrolidin-3-yl}sulfanyl)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
INN  Source
ertapenemKEGG DRUG
Synonyms  Source
(4R,5S,6S)-3-((3S,5S)-5-((3-carboxyphenyl)carbamoyl)pyrrolidin-3-ylthio)-6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acidChEMBL
ERTAPENEMChEMBL
(1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxyphenylcarbamoyl)pyrrolidin-4-ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acidChEBI
Manual XrefsDatabases
D07908KEGG DRUG
DB00303DrugBank
WO9315078Patent
US5478820Patent
ErtapenemWikipedia
1046DrugCentral
Registry NumbersSources
Beilstein:9025520Beilstein
CAS:153832-46-3KEGG DRUG
CAS:153832-46-3ChemIDplus