1936. Cefoxitin

Nomenclature

CAS number: 35607-66-0
(6R,7S)-3-[[(Aminocarbonyl)oxy]methyl]-7-methoxy-8-oxo-7-[[2-(2-thienyl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; 3-(hydroxymethyl)-7-methoxy-8-oxo-7-[2-(2-thienyl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid carbamate (ester); 3-carbamoyloxymethyl-7α-methoxy-7-[2-(2-thienyl)acetamido]-3-cephem-4-carboxylic acid.
C16H17N3O7S2; mol wt 427.45.
C 44.96%, H 4.01%, N 9.83%, O 26.20%, S 15.00%.

Description and references

Semi-synthetic, broad spectrum antibiotic derived from cephamycin C, q.v., possessing high resistance to β-lactamase inactivation. Synthesis: B. G. Christensen et al., DE 2129675; DE 2203653; eidem, US 4297488 (1971, 1972, 1981 all to Merck & Co.); Karady et al., J. Am. Chem. Soc. 94, 1410 (1972); Ratcliffe, Christensen, Tetrahedron Lett. 1973, 4653. Biological evaluation: Wallick, Hendlin, Antimicrob. Agents Chemother. 5, 25 (1974); Miller et al., ibid. 33; Onishi et al., ibid. 38; Hamilton, Miller et al., J. Antibiot. 27, 42 (1974). HPLC determn in serum and tissue: S. K. Cox et al., J. Chromatogr. B 705, 145 (1998). Mode of action: Onishi et al., Ann. N.Y. Acad. Sci. 235, 406 (1974). Toxicity: S. Takayama et al., Chemotherapy (Tokyo) 26, Suppl. 1, 150 (1978). Comprehensive reviews: J. Antimicrob. Chemother. 4, Suppl. B, 1-256 (1978); R. N. Brogden et al., Drugs 17, 1-37 (1979); E. O. Stapley, K. R. Brown, in Pharmacological and Biochemical Properties of Drug Substances vol. 3, M. E. Goldberg, Ed. (Am. Pharm. Assoc., Washington, DC, 1981) pp 262-290. Comprehensive description: G. S. Brenner, Anal. Profiles Drug Subs. 11, 169-195 (1982). Symposium on therapeutic use in anaerobic and aerobic infectons: Hosp. Pract. 25, Suppl. 4, 1-56 (1990).

Chemical structure

Properties

Crystals, mp 149-150° (dec). pKa 2.2. Very sol in acetone; sol in aq NaHCO3; very slightly sol in water. Practically insol in ether and chloroform.

Derivative

Sodium salt.

Nomenclature

CAS number: 33564-30-6
MK-306; Mefoxin (Merck & Co.); Mefoxitin (Merck & Co.).
C16H16N3NaO7S2; mol wt 449.43.
C 42.76%, H 3.59%, N 9.35%, Na 5.12%, O 24.92%, S 14.27%.

Properties

White crystals with characteristic odor. [α]25589nm +210° (c = 1 in methanol). Very sol in water; sol in methanol; sparingly sol in ethanol and acetone. Insol in aromatic and aliphatic hydrocarbons. LD50 in mice, rats, dogs (g/kg): 5.10, 8.98, >10.0 i.v. (Takayama).

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Antibiotics); β-Lactams; Cephamycins