Title: Lenampicillin
CAS Registry Number: 86273-18-9
CAS Name: (2S,5R,6R)-6-[[(2R)-Aminophenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl ester
Additional Names: ampicillin (5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl ester; 6-[D(-)-a-aminophenylacetamido]penicillanic acid (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl ester
Molecular Formula: C21H23N3O7S
Molecular Weight: 461.49
Percent Composition: C 54.65%, H 5.02%, N 9.11%, O 24.27%, S 6.95%
Literature References: Orally active ampicillin prodrug. Prepn: F. Sakamoto et al., EP 39086; eidem, US 4342693 (1981, 1982 both to Kanebo); F. Sakamoto et al., Chem. Pharm. Bull. 32, 2241 (1984); S. Ikeda et al., ibid. 4316. Metabolism in man, dogs, rats: N. Awata et al., Jpn. J. Antibiot. 38, 1776, 1785, C.A. 104, 161479u, 122550r (1985). Human pharmacokinetics: A. Saito, M. Nakashima, Antimicrob. Agents Chemother. 29, 948 (1986). Series of articles on antibacterial activity, mutagenicity, pharmacology, clinical trials: Chemotherapy (Tokyo) 32, Suppl. 8, pp 1-772 (1984). Acute toxicity data: F. Ogino et al., ibid. 31.
Derivative Type: Hydrochloride
CAS Registry Number: 80734-02-7
Manufacturers' Codes: KB-1585; KBT-1585
Trademarks: Takacillin (Torii); Varacillin (Kanebo)
Molecular Formula: C21H23N3O7S.HCl
Molecular Weight: 497.95
Percent Composition: C 50.65%, H 4.86%, N 8.44%, O 22.49%, S 6.44%, Cl 7.12%
Properties: Crystals from isopropanol-ethyl acetate, mp 145° (dec). LD50 in male, female rats, male, female mice (mg/kg): approx 10000, approx 10000, 8294, 8492 orally; 4362, 4471, 3576, 4284 s.c.; 876, 838, 711, 775 i.v.; in dogs (mg/kg): >300 orally (Ogino).
Melting point: mp 145° (dec)
Toxicity data: LD50 in male, female rats, male, female mice (mg/kg): approx 10000, approx 10000, 8294, 8492 orally; 4362, 4471, 3576, 4284 s.c.; 876, 838, 711, 775 i.v.; in dogs (mg/kg): >300 orally (Ogino)
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Penicillins. |