1197. Biapenem

Nomenclature

CAS number: 120410-24-4
6-[[(4R,5S,6S)-2-Carboxy-6-((1R)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-en-3-yl]thio]-6,7-dihydro-5H-pyrazolo[1,2-a][1,2,4]triazol-4-ium inner salt; (1R,5S,6S)-2-[(6,7-dihydro-5H-pyrazolo[1,2-a][1,2,4]-triazolium-6-yl)thio]-6-[(R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate; LJC-10627; L-627; CL-186815.
C15H18N4O4S; mol wt 350.39.
C 51.42%, H 5.18%, N 15.99%, O 18.26%, S 9.15%.

Description and references

1-β-methyl-carbapenem antibiotic. Prepn: T. Kumagai et al., EP 289801; eidem, US 4990613 (1988, 1991 both to Lederle). Total synthesis: Y. Nagao et al., J. Org. Chem. 57, 4243 (1992). Renal dehydropeptidase stability: M. Hikida et al., Antimicrob. Agents Chemother. 36, 481 (1992). In-vitro antimicrobial spectrum: H. M. Wexler et al., J. Antimicrob. Chemother. 33, 629 (1994); H. Y. Chen, D. M. Livermore, ibid. 949. Clinical pharmacokinetics: M. Nakashima et al., Int. J. Clin. Pharmacol. Ther. Toxicol. 31, 70 (1993). Clinical evaluation: H. Meguro et al., Jpn. J. Antibiot. 47, 903 (1994).

Chemical structure

Properties

Amorphous, pale yellow powder from acetone/water, occurs as hemihydrate. [α]D20 -32.9° (c = 0.5).

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Antibiotics); β-Lactams; Carbapenems