1918. Cefbuperazone

Nomenclature

CAS number: 76610-84-9
(6R,7S)-7-[[(2R,3S)-2-[[(4-Ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino]-3-hydroxy-1-oxobutyl]amino]-7-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7S)-7-[(2R,3S)-2-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-3-hydroxybutyramido]-7-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; 7β-[d-α-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-β-(S)-hydroxybutanamido]-7α-methoxy-3-[5-(1-methyl-1,2,3,4-tetrazolyl)thiomethyl]-Δ3-cephem-4-carboxylic acid.
C22H29N9O9S2; mol wt 627.65.
C 42.10%, H 4.66%, N 20.08%, O 22.94%, S 10.22%.

Description and references

Broad spectrum injectable cephamycin. Prepn: I. Saikawa et al., BE 879217; eidem, US 4263292 (1980, 1981 both to Toyama). Distribution of 14C-cefbuperazone in mice: eidem, Jpn. J. Antibiot. 35, 2159 (1982), C.A. 98, 11062w (1982). In vitro and in vivo antibacterial activity: M. Tai et al., Antimicrob. Agents Chemother. 22, 728 (1982). General pharmacology: A. Takai et al., Jpn. J. Antibiot. 35, 2139 (1982), C.A. 98, 65142r (1982). Absorption, distribution, excretion: I. Saikawa et al., ibid. 2163, C.A. 98, 100691t (1982). Series of articles on cefbuperazone: Chemotherapy (Tokyo) 30, Suppl. 3 (1982) 986 pp. Stability and degradation studies: S. Takano et al., Yakugaku Zasshi 103, 62 (1983).

Chemical structure

Properties

Solid, mp 118-120° (dec).

Derivative

Sodium salt.

Nomenclature

CAS number: 76648-01-6
T-1982; Keiperazon (Kaken); Tomiporan (Toyama).
C22H28N9NaO9S2; mol wt 649.63.
C 40.67%, H 4.34%, N 19.40%, Na 3.54%, O 22.17%, S 9.87%.

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Antibiotics); β-Lactams; Cephamycins