Title: Amdinocillin Pivoxil
CAS Registry Number: 32886-97-8
CAS Name: (2S,5R,6R)-6-[[(Hexahydro-1H-azepin-1-yl)methylene]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (2,2-dimethyl-1-oxopropoxy)methyl ester
Additional Names: pivaloyloxymethyl 6-[(hexahydro-1H-azepin-1-yl)methyleneamino]penicillanate; pivamdinocillin; pivmecillinam
Manufacturers' Codes: FL-1039
Trademarks: Selexid (susp.) (Leo Pharm)
Molecular Formula: C21H33N3O5S
Molecular Weight: 439.57
Percent Composition: C 57.38%, H 7.57%, N 9.56%, O 18.20%, S 7.29%
Literature References: Semi-synthetic antibiotic related to penicillin. Pivaloyloxymethyl ester of amdinocillin, q.v. Prepn: F. J. Lund, DE 2055531; idem, US 3957764 (1971, 1976 both to Lövens Kemiske Fabrik). HPLC stability analysis: R. B. Hagel, E. H. Waysek, J. Chromatogr. 178, 97 (1979). Bacteriological and pharmacokinetic study: T. Damsgaard et al., J. Antimicrob. Chemother. 5, 267 (1979). Metabolism: J. D. Anderson, M. A. Adams, Chemotherapy 25, 1 (1979). Clinical study: B. T. Andersen et al., Infection 8, 27 (1980). Toxicity study: S. Sato et al., Takeda Kenkyushoho 35, 179 (1976), C.A. 86, 115154w (1977).
Properties: Crystals from cyclohexane, mp 118.5-119.5°. [a]D20 +231° (c = 1 in 96% ethanol). LD50 in mice, rats (mg/kg): 475-480, 465 i.v.; 1736-1930, 1935-2100 s.c.; 3020, 9500-10000 orally (Sato).
Melting point: mp 118.5-119.5°
Optical Rotation: [a]D20 +231° (c = 1 in 96% ethanol)
Toxicity data: LD50 in mice, rats (mg/kg): 475-480, 465 i.v.; 1736-1930, 1935-2100 s.c.; 3020, 9500-10000 orally (Sato)
Derivative Type: Hydrochloride
CAS Registry Number: 32887-03-9
Trademarks: Selexid (tabl.) (Leo Pharm); Melysin (Takeda)
Molecular Formula: C21H33N3O5S.HCl
Molecular Weight: 476.03
Percent Composition: C 52.99%, H 7.20%, N 8.83%, O 16.81%, S 6.74%, Cl 7.45%
Properties: Crystals from methanol-diisopropyl ether, mp 172-173°. [a]D20 +219° (c = 1 in 0.1N HCl).
Melting point: mp 172-173°
Optical Rotation: [a]D20 +219° (c = 1 in 0.1N HCl)
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Penicillins. |