Title: Cefpirome
CAS Registry Number: 84957-29-9
CAS Name: 1-[[(6
R,7
R)-7-[[(2
Z)-(2-Amino-4-thiazolyl)(methoxyimino)acetyl]amino]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-6,7-dihydro-5
H-cyclopenta[
b]pyrindinium inner salt
Synonyms: 3-[(2,3-cyclopenteno-1-pyridinium)methyl]-7-[2-
syn-methoxyimino-2-(2-aminothiazol-4-yl)acetamido]ceph-3-em-4-carboxylate; 1-[[(6
R,7
R)-7-[2-(2-amino-4-thiazolyl)glyoxylamido]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-6,7-dihydro-5
H-1-pyrindinium hydroxide, inner salt, 72-(
Z)-(
O-methyloxime)
Manufacturers' Codes: HR-810
Molecular Formula: C22H22N6O5S2
Molecular Weight: 514.58
Percent Composition: C 51.35%, H 4.31%, N 16.33%, O 15.55%, S 12.46%
Literature References: Fourth generation cephalosporin antibiotic. Prepn: R. Lattrell
et al., GB 2098216 (1982 to Hoechst). Prepn of crystalline salts: W. Dürckheimer, R. Lattrell,
US 4609653 (1986 to Hoechst); and
in vitro antibacterial activity: G. Seibert
et al., Arzneim.-Forsch. 33, 1084 (1983). Physical properties: R. Lattrell
et al., Proc. 13th Int. Congr. Chemother. 4, part 99, 1 (1983). Comparative
in vitro antibacterial spectrum and b-lactamase stability: H. C. Neu
et al., Infection 13, 146 (1985). HPLC determn in serum and urine: H. Uihlein
et al., ibid. 16, 135 (1988). Clinical pharmacokinetics: J. Kavi
et al., J. Antimicrob. Chemother. 22, 911 (1988). Series of articles on laboratory and clinical evaluations:
ibid. 29, Suppl A 1-104 (1992). Toxicity studies: G. Horstmann, K. Engelbart,
Arzneim.-Forsch. 40, 1250 (1990); H. H. Donaubauer, D. Mayer,
J. Antimicrob. Chemother. 29, Suppl. A, 71 (1992).
Properties: LD50 in mice, rats (g/kg): 1.9-2.4, 1.9-2.15 i.v.; 3.8-4.2, 5.8-6.55 i.p. (Donaubauer, Mayer).
Toxicity data: LD50 in mice, rats (g/kg): 1.9-2.4, 1.9-2.15 i.v.; 3.8-4.2, 5.8-6.55 i.p. (Donaubauer, Mayer)
Derivative Type: Sulfate
CAS Registry Number: 98753-19-6
Trademarks: Broact (Shionogi); Cefrom (HMR); Keitin (Chugai)
Molecular Formula: C22H22N6O5S2.H2SO4
Molecular Weight: 612.66
Percent Composition: C 43.13%, H 3.95%, N 13.72%, O 23.50%, S 15.70%
Properties: Occurs as the monohydrate, crystals, dec 198-202°. [a]25D -4.7° (c = 5 in H2O). uv max: 265 nm (e 21100). Soly (aq buffer, pH 6.5) >50%.
Optical Rotation: [a]25D -4.7° (c = 5 in H2O)
Absorption maximum: uv max: 265 nm (e 21100)
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Cephalosporins.