3673. Ertapenem

Nomenclature

CAS number: 153832-46-3
[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; (1R,5S,6S,8R,2′S,4′S)-2-(2-(3-carboxyphenylcarbamoyl)pyrrolidin-4-ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid; ZD-443.
C22H25N3O7S; mol wt 475.51.
C 55.57%, H 5.30%, N 8.84%, O 23.55%, S 6.74%.

Description and 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 β-lactamase stability: J. Kohler et al., ibid. 43, 1170 (1999). Stability in aq solns: M. Zajac et al., J. Pharm. Biomed. Anal. 43, 445 (2007). 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, J. Chromatogr. 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). Review of clinical experience: O. Burkhardt et al., Expert Opin. Pharmacother. 8, 237-256 (2007).

Chemical structure

Derivative

Sodium salt.

Nomenclature

CAS number: 153773-82-1
MK-826; Invanz (Merck & Co.).
C22H24N3NaO7S; mol wt 497.50.
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.

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Antibiotics); β-Lactams; Carbapenems