724. Apalcillin

Nomenclature

CAS number: 63469-19-2
(2S,5R,6R)-6-[[(2R)-2-[[(4-Hydroxy-1,5-naphthyridin-3-yl)carbonyl]amino]-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid.
C25H23N5O6S; mol wt 521.55.
C 57.57%, H 4.44%, N 13.43%, O 18.41%, S 6.15%.

Description and references

Semi-synthetic antibiotic related to penicillin. Prepn of the potassium salt: H. Tobiki et al., ZA 7205865; eidem, US 3864329 (1973, 1975 both to Sumitomo); of the sodium salt: Y. Hirotada et al., US 4005075 (1977 to Sumitomo); H. Tobiki et al., Yakugaku Zasshi 100, 49 (1980), C.A. 93, 95179x (1980). Microbiological evaluation: H. Noguchi et al., Antimicrob. Agents Chemother. 9, 262 (1976). Analytical studies: I. Umeda et al., Yakugaku Zasshi 99, 717 (1979), C.A. 92, 11287z (1980). Series of articles on pharmacology, exptl and clinical effects: Chemotherapy (Tokyo) 26, Suppl. 2, 111-223 (1978). Pharmacokinetics in man: U. Busch et al., Arzneim.-Forsch. 32, 1131 (1982).

Chemical structure

Derivative

Sodium salt.

Nomenclature

CAS number: 58795-03-2
PC-904; Lumota (Thomae).
C25H22N5NaO6S; mol wt 543.53.
C 55.24%, H 4.08%, N 12.88%, Na 4.23%, O 17.66%, S 5.90%.

Properties

White cryst, sol in water.

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Antibiotics); β-Lactams; Penicillins