CHEBI:404903 - ertapenem

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ChEBI Name ertapenem
ChEBI ID CHEBI:404903
Definition Meropenem 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:471574
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Formula C22H25N3O7S
Net Charge 0
Average Mass 475.51500
Monoisotopic Mass 475.141
InChI InChI=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
InChIKey JUZNIMUFDBIJCM-ANEDZVCMSA-N
SMILES [H][C@]1(CN[C@@]([H])(C1)C(=O)Nc1cccc(c1)C(O)=O)SC1=C(N2C(=O)[C@]([H])([C@@H](C)O)[C@@]2([H])[C@H]1C)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.
antibacterial agent
A substance that kills or slows the growth of bacteria.
(via carbapenems )
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 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
ertapenem KEGG DRUG
Synonyms Sources
(1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxyphenylcarbamoyl)pyrrolidin-4-ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid ChEBI
(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 acid ChEMBL
ERTAPENEM ChEMBL
Manual Xrefs Databases
1046 DrugCentral
D07908 KEGG DRUG
DB00303 DrugBank
Ertapenem Wikipedia
US5478820 Patent
WO9315078 Patent
View more database links
Registry Numbers Types Sources
153832-46-3 CAS Registry Number ChemIDplus
153832-46-3 CAS Registry Number KEGG DRUG
9025520 Beilstein Registry Number Beilstein
Last Modified
22 February 2017