Cefatrizine

Title: Cefatrizine
CAS Registry Number: 51627-14-6
CAS Name: (6R,7R)-7-[[(2R)-Amino-(4-hydroxyphenyl)acetyl]amino]-8-oxo-3-[(1H-1,2,3-triazol-4-ylthio)methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Additional Names: 7-[D-a-amino-a-(4-hydroxyphenyl)acetamido]-3-(1,2,3-triazol-4(5)-ylthiomethyl)-3-cephem-4-carboxylic acid
Manufacturers' Codes: BL-S640; SKF-60771; S-640P
Trademarks: Cefaperos (Allard)
Molecular Formula: C18H18N6O5S2
Molecular Weight: 462.50
Percent Composition: C 46.74%, H 3.92%, N 18.17%, O 17.30%, S 13.87%
Literature References: Orally active semi-synthetic cephalosporin antibiotic. Prepn: G. L. Dunn, J. R. E. Hoover, DE 2316866; eidem, US 3867380 (1974, 1975 both to SK&F); D. Willner, L. B. Crast, DE 2364192 (1974 to Bristol-Myers), C.A. 81, 105538 (1974); G. L. Dunn et al., J. Antibiot. 29, 65 (1976). Prepn of the propylene glycolate: M. A. Kaplan, A. P. Granatek, DE 2500385; eidem, US 3970651 (1975, 1976 both to Bristol-Myers). In vitro and in vivo antibacterial activity and pharmacokinetic behavior: P. Actor et al., ibid. 28, 594 (1975); F. Leitner et al., Antimicrob. Agents Chemother. 7, 298 (1975). General pharmacological properties: M. Matsuzaki et al., Jpn. J. Antibiot. 29, 107 (1976), C.A. 85, 311g (1976). Determn in serum and urine by HPLC: E. Crombez et al., J. Chromatogr. 173, 165 (1979). Disposition of 14C-cefatrizine in man: R. C. Gaver, G. Deeb, Drug Metab. Dispos. 8, 157 (1980). Activity and clinical use: A. J. Weinstein, Drugs 20, 137 (1980). Acute toxicity: M. Matsuzaki et al., Jpn. J. Antibiot. 29, 612 (1976), C.A. 85, 171724y (1976). Toxicological studies: ibid. 639-686, C.A. 85, 171722w-171723x (1976). Series of articles on pharmacokinetics and clinical efficacy: Drugs Exp. Clin. Res. 11, 441-462 (1985).
Properties: Zwitterionic. LD50 in male, female mice, male, female rats (mg/kg): 6880, 6410, 4325, 4325 i.p. (Matsuzaki).
Toxicity data: LD50 in male, female mice, male, female rats (mg/kg): 6880, 6410, 4325, 4325 i.p. (Matsuzaki)
Derivative Type: Compd with propylene glycol
CAS Registry Number: 64217-62-5
Trademarks: Bricef (BMS); Cepticol (Banyu); Cefotrizin (Firma); Faretrizin (Lafare); Kefoxina (CT); Tamyl (Italchimici); Zitrix (Metapharma)
Molecular Formula: C18H18N6O5S2.C3H8O2
Molecular Weight: 538.60
Percent Composition: C 46.83%, H 4.87%, N 15.60%, O 20.79%, S 11.91%
Properties: Rod-like crystals. [a]D23 +55.9° (c = 1% in 1N HCl). uv max: 227, 272 nm.
Optical Rotation: [a]D23 +55.9° (c = 1% in 1N HCl)
Absorption maximum: uv max: 227, 272 nm
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Cephalosporins.
Cefazedone Cefazolin Cefbuperazone Cefcapene Pivoxil Cefclidin

Cefatrizine
Cefatrizine.svg
Systematic (IUPAC) name
(6R,7R)-7-{[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]
amino}-8-oxo-3-[(1H-1,2,3-triazol-4-ylsulfanyl)methyl]-
5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Clinical data
AHFS/Drugs.com International Drug Names
Legal status  ?
Routes Oral
Identifiers
CAS number 64217-62-5
ATC code J01DB07
PubChem CID 6410758
ChemSpider 4918615 YesY
UNII 8P4W949T8K YesY
KEGG D02711 YesY
ChEMBL CHEMBL1095284 YesY
Chemical data
Formula C18H18N6O5S2 
Mol. mass 462.505 g/mol
 YesY (what is this?)  (verify)

Cefatrizine is a broad-spectrum cephalosporin antibiotic.