Title: Carumonam
CAS Registry Number: 87638-04-8
CAS Name: [[(Z)-[2-[[(2S,3S)-2-[[(Aminocarbonyl)oxy]methyl]-4-oxo-1-sulfo-3-azetidinyl]amino]-1-(2-amino-4-thiazolyl)-2-oxoethylidene]amino]oxy]acetic acid
Additional Names: (Z)-[[[(2-amino-4-thiazolyl)[[(2S,3S)-2-(hydroxymethyl)-4-oxo-1-sulfo-3-azetidinyl]carbamoyl]methylene]amino]oxy]acetic acid carbamate (ester); (3S,4S)-cis-3-[2-(2-amino-4-thiazolyl)-2-(Z)-carboxymethoxyiminoacetamido]-4-carbamoyloxymethyl-2-azetidinone-1-sulfonic acid
Molecular Formula: C12H14N6O10S2
Molecular Weight: 466.40
Percent Composition: C 30.90%, H 3.03%, N 18.02%, O 34.30%, S 13.75%
Literature References: Synthetic monocyclic b-lactam (monobactam) antibiotic. Prepn: S. Kishimoto et al., EP 93376; T. Matsuo et al., US 4572801 (1983, 1986 both to Takeda); M. Sendai et al., J. Antibiot. 38, 346 (1985). Alternate synthesis: P. S. Manchard et al., J. Org. Chem. 53, 5507 (1988). Comparative in vitro antimicrobial activity: R. J. Fass, V. L. Helsel, Antimicrob. Agents Chemother. 28, 834 (1985); B. R. Smith et al., ibid. 29, 346 (1986); I. M. Hoepelman et al., Chemotherapy (Basel) 33, 103 (1987). b-Lactamase stability: R. L. Then, ibid. 30, 398 (1984). Pharmacokinetics in humans: E. Weidekamm et al., Antimicrob. Agents Chemother. 26, 898 (1984); C. A. M. McNulty et al., ibid. 28, 425 (1985).
Properties: Colorless powder. [a]D26 -45° (c = 1 in DMSO).
Optical Rotation: [a]D26 -45° (c = 1 in DMSO)
Derivative Type: Disodium salt
CAS Registry Number: 86832-68-0
Manufacturers' Codes: AMA-1080; Ro-17-2301
Trademarks: Amasulin (Takeda); Mobactam (Takeda)
Molecular Formula: C12H12N6Na2O10S2
Molecular Weight: 510.37
Percent Composition: C 28.24%, H 2.37%, N 16.47%, Na 9.01%, O 31.35%, S 12.57%
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Monobactams. |