87638-04-8

Basic information

• Product Name: CARUMONAM
• Synonyms: CARUMONAM;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]-;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)]]-;AMA 1080;Antibiotic Ro 17-2301;Ro 17-2301;[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;CarlliIIonaln
• CAS NO: 87638-04-8
• Molecular Formula: C12H14N6O10S2
• Molecular Weight: 466.4
• Mol File: 87638-04-8.mol
• Article Data: 1

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 2.13g/cm³
• Refractive Index: 1.82
• PKA: -0.43±0.60(Predicted)
• CAS DataBase Reference: CARUMONAM(CAS DataBase Reference)
• NIST Chemistry Reference: CARUMONAM(87638-04-8)
• EPA Substance Registry System: CARUMONAM(87638-04-8)

Safety Data

• Hazardous Substances Data: 87638-04-8(Hazardous Substances Data)

Usage

Description

CARUMONAM, also known as Amasulin, is an injectable antibiotic and the second monobactam ever developed, following Squibb's aztreonam. It is characterized as an N-sulfonated monobactam antibiotic with a strong affinity for Gram-negative bacteria, particularly Pseudomonas aeruginosa. CARUMONAM is recognized for its effectiveness in treating various infections, including pneumonia, cystitis, peritonitis, and secondary infections.

Uses

Used in Pharmaceutical Industry:
CARUMONAM is used as an antibiotic for the treatment of infections caused by Gram-negative bacteria, specifically targeting Pseudomonas aeruginosa. Its application is particularly beneficial in managing pneumonia, cystitis, peritonitis, and secondary infections, providing an effective therapeutic option for patients suffering from these conditions.

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.

InChI:InChI=1/C12H14N6O10S2/c13-11-15-4(3-29-11)7(17-28-2-6(19)20)9(21)16-8-5(1-27-12(14)23)18(10(8)22)30(24,25)26/h3,5,8H,1-2H2,(H2,13,15)(H2,14,23)(H,16,21)(H,19,20)(H,24,25,26)/b17-7-/t5?,8-/m0/s1

Upstream product

• 88852-06-6 (3S,4S)-3-amino-4-[(carbamoyloxy)methyl]-2-oxo-azetidine-1-sulfonic acid 

Relevant articles and documents

Synthesis of carumonam (AMA-1080) and a related compound starting from (2R,3R)-epoxysuccinic acid

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