7009. Panipenem
Nomenclature
CAS number: 87726-17-8
(5R,6S)-6-[(1R)-1-Hydroxyethyl]-3-[[(3S)-1-(1-iminoethyl)-3-pyrrolidinyl]thio]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic
acid; (5R,6S)-6-[(R)-1-hydroxyethyl]-2-[(S)-1-acetimidoylpyrrolidin-3-ylthio]-1-carbapen-2-em-3-carboxylic
acid; (+)-(5R,6S)-3-[[(S)-1-acetimidoyl-3-pyrrolidinyl]thio]-6-[(R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic
acid; CS-533; RS-533. C15H21N3O4S; mol wt 339.41.
C 53.08%, H 6.24%, N 12.38%, O 18.86%, S 9.45%.
Description and references
Carbapenem antibiotic. Prepn: T. Miyadera et al., J. Antibiot. 36, 1034 (1983). Manufacturing process: A. Yoshida, K. Oda, EP 587436 (1994 to Sankyo). Antibacterial spectrum in vitro: H. C. Neu et al., Antimicrob. Agents Chemother. 30, 828 (1986). Series of articles on pharmacology and clinical efficacy in combination with betamipron, q.v: Chemotherapy (Tokyo) 39 Suppl 3, 1-813 (1991). Toxicology: K. Kimura et al., ibid. 140.
Properties
Prepd as the hemihydrate; colorless fine prisms, mp 198-200° (dec). uv max (water): 298 nm (ε 10400). Approx LD50 in male, female mice (mg/kg): 1700-2200, 1300-1700 i.v. (Kimura).Derivative
Mixture with betamipron.Nomenclature
CAS number: 138240-65-0
CS-976; Carbenin (Sankyo). Therapeutic Category
Antibacterial.
Keywords
Antibacterial (Antibiotics); β-Lactams; Carbapenems