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87638-04-8

87638-04-8 Structure

87638-04-8 Structure
IdentificationBack Directory
[Name]

CARUMONAM
[CAS]

87638-04-8
[Synonyms]

AMA 1080
CARUMONAM
Ro 17-2301
CarlliIIonaln
CARUMONAM USP/EP/BP
Ro-17-2301:A-masulin
Antibiotic Ro 17-2301
(2S)-2α-(Carbamoyloxymethyl)-3α-[[(Z)-(2-amino-4-thiazolyl)[(carboxymethoxy)imino]acetyl]amino]-4-oxoazetidine-1-sulfonic acid
[[[(Z)-2-[[(2S)-2α-[[(Aminocarbonyl)oxy]methyl]-4-oxo-1-sulfoazetidin-3α-yl]amino]-1-(2-aminothiazol-4-yl)-2-oxoethylidene]amino]oxy]acetic acid
[[[(Z)-2-[[(2S,3S)-2-[[(Aminocarbonyl)oxy]methyl]-4-oxo-1-sulfoazetidin-3-yl]amino]-1-(2-amino-4-thiazolyl)-2-oxoethylidene]amino]oxy]acetic acid
Acetic acid, [[(Z)-[2-[[(2S,3S)-2-[[(aminocarbonyl)oxy]methyl]-4-oxo-1-sulfo-3-azetidinyl]amino]-1-(2-amino-4-thiazolyl)-2-oxoethylidene]amino]oxy]-
[2S-[2α,3α(Z)]]-[[[2-[[2-[[(Aminocarbonyl)oxy]methyl]-4-oxo-1-sulfo-3-azetidinyl]amino]-1-(2-amino-4-thiazolyl)-2-oxoethylidene]amino]oxy]acetic acid
Acetic acid, 2-[[(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, [[[2-[[2-[[(aminocarbonyl)oxy]methyl]-4-oxo-1-sulfo-3-azetidinyl]amino]-1-(2-amino-4-thiazolyl)-2-oxoethylidene]amino]oxy]-, [2S-[2α,3α(Z)]]-
[Molecular Formula]

C12H14N6O10S2
[MDL Number]

MFCD00871292
[MOL File]

87638-04-8.mol
[Molecular Weight]

466.4
Chemical PropertiesBack Directory
[alpha ]

D26 -45° (c = 1 in DMSO)
[density ]

2.13±0.1 g/cm3(Predicted)
[pka]

-0.43±0.60(Predicted)
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Sodium borohydride-->Benzyl chloroformate-->2,3-Di-O-para-toluoyl-D-tartaric acid
Hazard InformationBack Directory
[Description]

Canunonam is an injectable antibiotic, the second monobactam ever developed (the first being Squibb’s aztreonam). It is highly active against Gram negative bacteria, particularly pseudomom, and is reportedly effective in the treatment of pneumonia, cystitis, peritonitis and secondary infections.
[Chemical Properties]

Colorless powder. [α]D26-45°(C=1, dimethyl sulfoxide)
[Originator]

Takeda (Japan)
[Uses]

CARUMONAM is monocyclic β-lactam antibiotics. Their antibacterial spectrum is similar to amantadine, exhibiting high antibacterial activity against Gram-negative bacteria. While their activity against Pseudomonas aeruginosa is slightly weaker than amantadine and ceftazidime, it is better than other antibiotics. They are highly effective against Klebsiella pneumoniae and are also effective against bacteria resistant to gentamicin and third- and fourth-generation cephalosporins. They are very stable against various bacterial inulinases and chromosomal or plasmid-mediated β-lactamases. They are used for sepsis, chronic respiratory infections, cholangitis, peritonitis, chronic bronchitis, and cystitis caused by susceptible bacteria.
[Definition]

ChEBI: An N-sulfonated monobactam antibiotic.
[Brand name]

Amasulin
[Antimicrobial activity]

A synthetic monobactam with activity against common pathogenic organisms similar to that of aztreonam. It is resistant to hydrolysis by the common plasmid and chromosomal β-lactamases, but it can be hydrolyzed by ESBLs.
It is administered intravenously, achieving a concentration of c. 78 mg/L after a 20-min infusion of 1 g. The plasma halflife is 1.7 h and the plasma protein binding 18–28%. Carumonam is almost entirely eliminated in the glomerular filtrate, probenecid having no effect on excretion; 96% of labeled compound is found in the urine, with 3% in the feces. Between 68% and 91% of the dose appears in the urine within 24 h.
Side effects and clinical use are similar to those of aztreonam.
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