Ertapenem

Title: Ertapenem
CAS Registry Number: 153832-46-3
CAS Name: [4R,5S,6S]-3-[[(3S,5S)-5-[[(3-Carboxyphenyl)amino]carbonyl]-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
Additional Names: (1R,5S,6S,8R,2¢S,4¢S)-2-(2-(3-carboxyphenylcarbamoyl)pyrrolidin-4-ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid
Manufacturers' Codes: ZD-443
Molecular Formula: C22H25N3O7S
Molecular Weight: 475.51
Percent Composition: C 55.57%, H 5.30%, N 8.84%, O 23.55%, S 6.74%
Literature References: Group 1 carbapenem antibiotic. Prepn: M. J. Betts et al., WO 9315078; eidem, US 5478820 (1993, 1995 both to Zeneca). Large-scale synthesis: J. M. Williams et al., J. Org. Chem. 70, 7479 (2005). Pharmacokinetics in primates: J. G. Sundelof et al., Antimicrob. Agents Chemother. 41, 1743 (1997). In vivo efficacy and pharmacokinetics: C. J. Gill et al., ibid. 42, 1996 (1998). In vitro efficacy and b-lactamase stability: J. Kohler et al., ibid. 43, 1170 (1999). HPLC determn in plasma and urine: D. G. Musson et al., J. Chromatogr. B 720, 99 (1998); of residual crystallization solvents: T. K. Natishan, Y. Wu, ibid. A 800, 275 (1998). Series of articles on pharmacology and clinical experience in complicated community-acquired infections: J. Antimicrob. Chemother. 53, Suppl. S2, ii1-ii86 (2004).
Derivative Type: Sodium salt
CAS Registry Number: 153832-38-3
Manufacturers' Codes: MK-826
Trademarks: Invanz (Merck & Co.)
Molecular Formula: C22H24N3NaO7S
Molecular Weight: 497.50
Percent Composition: C 53.11%, H 4.86%, N 8.45%, Na 4.62%, O 22.51%, S 6.45%
Properties: White to off-white hygroscopic, weakly crystalline powder. Sol in water, 0.9% sodium chloride soln. Practically insol in ethanol; insol in isopropyl acetate, THF.
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Carbapenems.
Erucic Acid Erythritol Erythritol Anhydride Erythrityl Tetranitrate Erythrocentaurin

Ertapenem
Ertapenem Formula V.1.svg
Systematic (IUPAC) name
(4R,5S,6S)-3-[(3S,5S)-5-[(3-carboxyphenyl)carbamoyl]
pyrrolidin-3-yl]sulfanyl-6-(1-hydroxyethyl)-4-methyl-7-
oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
Clinical data
Trade names Invanz
AHFS/Drugs.com monograph
Pregnancy cat. B3 (AU) B (US)
Legal status Prescription only
Routes Intramuscular, intravenous
Pharmacokinetic data
Bioavailability 90% (intramuscular)
Protein binding Inversely proportional to concentration; 85 to 95%
Metabolism Minor hydrolysis of beta-lactam ring, CYP not involved
Half-life 4 hours
Excretion Renal (80%) and fecal (10%)
Identifiers
CAS number 153832-46-3 YesY
ATC code J01DH03
PubChem CID 150610
DrugBank DB00303
ChemSpider 132758 YesY
UNII G32F6EID2H YesY
KEGG D04049 N
ChEBI CHEBI:404903 YesY
ChEMBL CHEMBL1359 YesY
Chemical data
Formula C22H25N3O7S 
Mol. mass 475.516 g/mol
 N (what is this?)  (verify)

Ertapenem is a carbapenem antibiotic marketed by Merck as Invanz. It is structurally very similar to meropenem in that it possesses a 1-β-methyl group.