Title: Panipenem
CAS Registry Number: 87726-17-8
CAS Name: (5
R,6
S)-6-[(1
R)-1-Hydroxyethyl]-3-[[(3
S)-1-(1-iminoethyl)-3-pyrrolidinyl]thio]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
Synonyms: (5
R,6
S)-6-[(
R)-1-hydroxyethyl]-2-[(
S)-1-acetimidoylpyrrolidin-3-ylthio]-1-carbapen-2-em-3-carboxylic acid; (+)-(5
R,6
S)-3-[[(
S)-1-acetimidoyl-3-pyrrolidinyl]thio]-6-[(
R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
Manufacturers' Codes: CS-533; RS-533
Molecular Formula: C15H21N3O4S
Molecular Weight: 339.41
Percent Composition: C 53.08%, H 6.24%, N 12.38%, O 18.86%, S 9.45%
Literature 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 (e 10400). Approx LD50 in male, female mice (mg/kg): 1700-2200, 1300-1700 i.v. (Kimura).
Melting point: mp 198-200° (dec)
Absorption maximum: uv max (water): 298 nm (e 10400)
Toxicity data: Approx LD50 in male, female mice (mg/kg): 1700-2200, 1300-1700 i.v. (Kimura)
Derivative Type: Mixture with betamipron
CAS Registry Number: 138240-65-0
Manufacturers' Codes: CS-976
Trademarks: Carbenin (Sankyo)
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Carbapenems.