Cefpirome

Title: Cefpirome
CAS Registry Number: 84957-29-9
CAS Name: 1-[[(6R,7R)-7-[[(2Z)-(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-5H-cyclopenta[b]pyrindinium inner salt
Additional Names: 3-[(2,3-cyclopenteno-1-pyridinium)methyl]-7-[2-syn-methoxyimino-2-(2-aminothiazol-4-yl)acetamido]ceph-3-em-4-carboxylate; 1-[[(6R,7R)-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-5H-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.
Cefpodoxime Proxetil Cefprozil Cefquinome Cefroxadine Cefsulodin

Cefpirome
Cefpirome.svg
Systematic (IUPAC) name
1-{[(6R,7R)-7-[(2E)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-2-carboxylato-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}-5H,6H,7H-cyclopenta[b]pyridin-1-ium
Clinical data
AHFS/Drugs.com International Drug Names
Legal status  ?
Identifiers
CAS number 84957-29-9 YesY
ATC code J01DE02
PubChem CID 6917674
ChemSpider 23089536 N
UNII S72Q2F09HY YesY
KEGG D07649 YesY
Chemical data
Formula C22H22N6O5S2 
Mol. mass 514.58 g/mol
 N (what is this?)  (verify)

Cefpirome is a fourth-generation cephalosporin. Trade names include Cefrom, Keiten, Broact, Cefir. Cefpirome is considered highly active against Gram-negative bacteria, including Pseudomonas aeruginosa, and Gram-positive bacteria. It is marketed under the brand name of CEFROM by sanofi aventis group india .