Ertapenem
(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
Molecular Identity
Ertapenem
(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
PubChem CID: 150610
Ertapenem is 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. It has a role as an antibacterial drug. It is a carbapenemcarboxylic acid and a pyrrolidinecarboxamide. It is a conjugate acid of an ertapenem(1-).
2D Structure
Properties
C22H25N3O7S
Molecular Formula
475.50
Molecular Weight
g/mol
475.1413
Exact Mass
Da
-1.5
XLogP
Drug-like (Lipinski: < 5)
182
TPSA
May have limited oral absorption
5
H-Bond Donors
9
H-Bond Acceptors
893
Complexity
SMILES
Canonical SMILES
SMILES: Synonyms(20)
Ertapenem153832-46-3(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 acidG32F6EID2H(1R,5S,6S,8R,2'S,4'S)-2-(2-(3-carboxyphenylcarbamoyl)pyrrolidin-4-ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acidCHEBI:404903DTXSID50165456(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(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(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 acid1-Azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 3-(((3S,5S)-5-(((3-carboxyphenyl)amino)carbonyl)-3-pyrrolidinyl)thio)-6-((1R)-1-hydroxyethyl-4-methyl-7-oxo-, (4R,5S,6S)-1-Azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 3-((5-(((3-carboxyphenyl)amino)carbonyl)-3-pyrrolidinyl)thio)-6-(1-hydroxyethyl)-4-methyl-7-oxo-, (4R-(3(3S*,5S*),4alpha,5beta,6beta(R*)))-ertapenemum(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(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
Data from PubChem (NCBI)
This platform is for informational purposes only and does not constitute medical advice. Always consult a qualified healthcare professional.