1916. Cefazedone

Nomenclature

CAS number: 56187-47-4
(6R,7R)-7-[[(3,5-Dichloro-4-oxo-1(4H)-pyridinyl)acetyl]amino]-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; 3-(5-methyl-1,3,4-thiadiazolyl-2-mercaptomethyl)-7-(3,5-dichloro-4-pyridon-1-ylacetamido)-3-cephem-4-carboxylic acid; EMD-30087.
C18H15Cl2N5O5S3; mol wt 548.44.
C 39.42%, H 2.76%, Cl 12.93%, N 12.77%, O 14.59%, S 17.54%.

Description and references

Semi-synthetic cephalosporin antibiotic. Prepn: R. Gerike et al., DE 2345402; eidem, US 4153693 (1975, 1979 both to E. Merck, W. Ger.). See also eidem, DE 2621011, DE 2626026, DE 2627204 (all 1977 to E. Merck, W. Ger.), C.A. 88, 5093, 105383, 121213 (1978). Series of articles on prepn, in vitro and in vivo activity, kinetics, pharmacology, toxicology, and clinical trials: Arzneim.-Forsch. 29, 361-462 (1979). Toxicity data: M. von Eberstein et al., ibid. 424.

Chemical structure

Properties

Crystals from acetonitrile.

Derivative

Sodium salt.

Nomenclature

CAS number: 63521-15-3
Refosporin (Merck KGaA).
C18H14Cl2N5NaO5S3; mol wt 570.43.
C 37.90%, H 2.47%, Cl 12.43%, N 12.28%, Na 4.03%, O 14.02%, S 16.86%.

Properties

LD50 in mice, rats, rabbits, dogs (mg/kg): 6800, 4225, 3200, 3000 i.v. (von Eberstein).

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Antibiotics); β-Lactams; Cephalosporins