Title: Ertapenem
CAS Registry Number: 153832-46-3
CAS Name: [4
R,5
S,6
S]-3-[[(3
S,5
S)-5-[[(3-Carboxyphenyl)amino]carbonyl]-3-pyrrolidinyl]thio]-6-[(1
R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
Synonyms: (1
R,5
S,6
S,8
R,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.