9033. Talampicillin
Nomenclature
CAS number: 47747-56-8
(2S,5R,6R)-6-[[(2R)-Aminophenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic
acid 1,3-dihydro-3-oxo-1-isobenzofuranyl ester; (2S,5R,6R)-6-[(R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic
acid ester with 3-hydroxyphthalide; 6-[d()-α-aminophenylacetamido]penicillanic acid phthalide
ester; ampicillin 1-oxo-1,3-dihydroisobenzofuran-3-yl ester; phthalidyl d-α-aminobenzylpenicillanate. C24H23N3O6S; mol wt 481.52.
C 59.86%, H 4.81%, N 8.73%, O 19.94%, S 6.66%.
Description and references
Semi-synthetic antibiotic related to penicillin. Prepn: H. Ferres, M. P. Clayton, DE 2228012; eidem, US 3860579 (1972, 1975 both to Beecham). See also: M. Murakami et al., US 3951954 (1976 to Yamanouchi). Pharmacology: Clayton et al., Antimicrob. Agents Chemother. 5, 670 (1974). HPLC determn in urine and comparison of pharmacokinetics with other aminopenicillins: T. Uno et al., Chem. Pharm. Bull. 29, 1957 (1981). Clinical comparison with ampicillin, q.v.: H. N. Williams et al., Br. J. Clin. Pract. 35, 147 (1981).
Derivative
Hydrochloride.Nomenclature
CAS number: 39878-70-1
BRL-8988; Talat (Polifarma); Talpen (SKB); Yamacillin (Yamanouchi). C24H23N3O6S.HCl; mol wt 517.98.
C 55.65%, H 4.67%, N 8.11%, O 18.53%, S 6.19%, Cl 6.84%.
Properties
White powder, mp 154-157° (dec).Therapeutic Category
Antibacterial.
Keywords
Antibacterial (Antibiotics); β-Lactams; Penicillins