1871. Carumonam

Nomenclature

CAS number: 87638-04-8
[[(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; (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.
C12H14N6O10S2; mol wt 466.40.
C 30.90%, H 3.03%, N 18.02%, O 34.30%, S 13.75%.

Description and references

Synthetic monocyclic β-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). β-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).

Chemical structure

Properties

Colorless powder. [α]D26 -45° (c = 1 in DMSO).

Derivative

Disodium salt.

Nomenclature

CAS number: 86832-68-0
AMA-1080; Ro-17-2301; Amasulin (Takeda); Mobactam (Takeda).
C12H12N6Na2O10S2; mol wt 510.37.
C 28.24%, H 2.37%, N 16.47%, Na 9.01%, O 31.35%, S 12.57%.

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Antibiotics); β-Lactams; Monobactams