852. Aspoxicillin

Nomenclature

CAS number: 63358-49-6
(2R)-N-Methyl-d-asparaginyl-N-[(2S,5R,6R)-2-carboxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-6-yl]-2-(4-hydroxyphenyl)glycinamide; 6-[d-2-(d-2-amino-3-N-methylcarbamoylpropionamido)-2-p-hydroxyphenylacetamido]penicillanic acid; (2S,5R,6R)-6-[(2R)-2-[(2R)-2-amino-3-(methylcarbamoyl)propionamido]-2-(p-hydroxyphenyl)acetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; N4-methyl-d-asparaginylamoxicillin; ASPC; TA-058; Doyle (Tanabe Seiyaku).
C21H27N5O7S; mol wt 493.53.
C 51.11%, H 5.51%, N 14.19%, O 22.69%, S 6.50%.

Description and references

Semisynthetic penicillin. Prepn: M. Kawazu et al., DE 2638067; eidem, US 4053609 (both 1977 to Tanabe); prepn and antibacterial activity: M. Wagatsuma et al., J. Antibiot. 36, 147 (1985). Mechanism of action study: T. Nishino et al., Chemotherapy (Tokyo) 33, 132 (1985), C.A. 103 34792v (1985). Toxicological study: M. Takeshita et al., Oyo Yakuri 30, 687 (1985), C.A. 104, 101990u (1986). HPLC determn in serum: J. Knller et al., Zentralbl. Bakteriol. Mikrobiol. Hyg. 265, 176 (1987). Clinical evaluation in ocular infections: M. Ooishi et al., Acta Med. Biol. 34, 1 (1986). Series of articles on antibacterial activity, pharmacology and clinical efficacy: Chemotherapy (Tokyo) 32, Suppl. 2, 1-791 (1984).

Chemical structure

Properties

Colorless crystalline powder, mp 195-198° (dec).

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Antibiotics); β-Lactams; Penicillins