Synthesis of sulfazecin-type 2-azetidinones with a carbon substituent at the 4-position.

Kishimoto, Shinji; Sendai, Michiyuki; Hashiguchi, Shohei; Tomimoto, Mitsumi; Satoh, Yoshiaki; Matsuo, Taisuke; Kondo, Masahiro; Ochiai, Masahito

doi:10.7164/antibiotics.36.1421

Cited by 24 publications

(8 citation statements)

References 6 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Tokyo, p. 9,1982). Of the sulfazecinrelated compounds chemically synthesized, carumonam (AMA-1080, Ro 17-2301), (3S,4S)-3-[2-(2-aminothiazol-4-yl)-(Z) -2 -carboxymethoxyiminoacetamido] -4 -carbamoyloxymethyl-2-azetidinone-1-sulfonic acid (5) (Fig. 1), was selected for further development, and its in vitro and in vivo activities, affinity for penicillin-binding proteins (PBPs), and interaction with P-lactamases were compared with those of another sulfazecin-type antibiotic, aztreonam (13), and thirdgeneration cephalosporins, cefoperazone (7) and ceftazidime (10).…”

mentioning

confidence: 99%

In vitro and in vivo antibacterial activities of carumonam (AMA-1080), a new N-sulfonated monocyclic beta-lactam antibiotic

Imada¹,

Kondo²,

Okonogi³

et al. 1985

Antimicrob Agents Chemother

View full text Add to dashboard Cite

show abstract

mentioning

confidence: 99%

In vitro and in vivo antibacterial activities of carumonam (AMA-1080), a new N-sulfonated monocyclic beta-lactam antibiotic

Imada¹,

Kondo²,

Okonogi³

et al. 1985

Antimicrob Agents Chemother

View full text Add to dashboard Cite

show abstract

“…Ro 17-2301 (AMA-1080) is a new sulfa zecin-type antibiotic, the synthesis of which has recently been described [8,11]. It exhibits high activity against a broad range of gram-negative organisms includ ing Pseudomonas aeruginosa [ 1,2,5,9].…”

Section: Introductionmentioning

confidence: 99%

Interaction of Ro 17–2301 (AMA-1080) with <i>β</i>-Lactamases

Rl¹

1984

Chemotherapy

View full text Add to dashboard Cite

Against a variety of β-lactamases tested, mostly of chromosomal origin, Ro 17–2301 (AMA-1080) proved to be more stable than the new cephalosporins and thus resembles aztreonam. Against the β-lactamases from Klebsiella oxytoca and Pseudomonas vulgaris, however, Ro 17–2301 proved to be much more stable than aztreonam. Enzymatic hydrolysis, performed with the K. oxytoca β-lactamase, yielded a single compound, viz. the microbiologically inactive, ring-opened structure. Ro 17–2301 is a potent and progressive inhibitor of cephalosporinases found, e.g., in Enterobacter cloacae and other gram-negative organisms. The IC₅₀ and K_i values, however, showed that the affinity for these enzymes is lower than that of aztreonam.

show abstract

“…One of them is carumonam (Ro 17-2301, AMA-1080; fig. 1), the synthesis of which has been published by Kishimoto et al [6], The antibacterial prop erties of this new antibiotic were evalu ated in the present study.…”

Section: Introductionmentioning

confidence: 99%

Antibacterial Properties of Carumonam (Ro 17–2301, AMA-1080), a New Sulfonated Monocyclic <i>β</i>-Lactam Antibiotic

Angehrn¹

1985

Chemotherapy

View full text Add to dashboard Cite

The in vitro and in vivo activity of carumonam was tested in comparison with that of aztreonam and other β-lactam antibiotics. With the exception of a few isolates that were overproducers of cephalosporinase, Enterobacteriaceae were highly susceptible to carumonam, 90% of the isolates being inhibited at 0.5 μg/ml. Aztreonam, ceftriaxone and ceftazidime were overall slightly less active than carumonam against Enterobacteriaceae. Carumonam was intermediate between ceftazidime and aztreonam as to the activity against Pseudomonas aeruginosa. Staphylococci were resistant to the monocyclic β-lactams. In accordance with the in vitro data, carumonam was effective against experimental septicemias and infections of the thigh and the kidney that were caused by gram-negative pathogens.

show abstract

Synthesis of sulfazecin-type 2-azetidinones with a carbon substituent at the 4-position.

Cited by 24 publications

References 6 publications

In vitro and in vivo antibacterial activities of carumonam (AMA-1080), a new N-sulfonated monocyclic beta-lactam antibiotic

In vitro and in vivo antibacterial activities of carumonam (AMA-1080), a new N-sulfonated monocyclic beta-lactam antibiotic

Interaction of Ro 17–2301 (AMA-1080) with <i>β</i>-Lactamases

Antibacterial Properties of Carumonam (Ro 17–2301, AMA-1080), a New Sulfonated Monocyclic <i>β</i>-Lactam Antibiotic

Contact Info

Product

Resources

About