859-07-4

Basic information

• Product Name: cefaloram
• Synonyms: cefaloram;Cephalosporin G;(6R,7R)-3-(Acetoxymethyl)-8-oxo-7-[(phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;(7R)-3-(Acetoxymethyl)-7β-[(α-oxophenethyl)amino]cepham-3-ene-4-carboxylic acid;(7R)-7-(Phenylacetylamino)-3-(acetoxymethyl)cepham-3-ene-4-carboxylic acid;(6R,7R)-3-(acetoxymethyl)-8-keto-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;(6R,7R)-3-(acetyloxymethyl)-8-oxo-7-(2-phenylethanoylamino)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;(6R,7R)-3-(acetyloxymethyl)-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS NO: 859-07-4
• Molecular Formula: C₁₈H₁₈N₂O₆S
• Molecular Weight: 390.414
• EINECS: 212-725-1
• Mol File: 859-07-4.mol
• Article Data: 18

Chemical Properties

• Melting Point: 160-162 °C (decomp)
• Boiling Point: 742.8°C at 760 mmHg
• Flash Point: 403°C
• Appearance: /
• Density: 1.48g/cm³
• Vapor Pressure: 3.58E-23mmHg at 25°C
• Refractive Index: 1.66
• PKA: 2.68±0.50(Predicted)
• CAS DataBase Reference: cefaloram(CAS DataBase Reference)
• NIST Chemistry Reference: cefaloram(859-07-4)
• EPA Substance Registry System: cefaloram(859-07-4)

Safety Data

• Hazardous Substances Data: 859-07-4(Hazardous Substances Data)

Usage

General Description

Cefaloram is an antibiotic medication belonging to the cephalosporin class, specifically a second-generation cephalosporin. It is used to treat a variety of bacterial infections, including respiratory tract, urinary tract, skin, and soft tissue infections. Cefaloram works by inhibiting the synthesis of the bacterial cell wall, leading to the disruption of the bacterial cell membrane and ultimately causing the death of the bacteria. It is typically administered intravenously or intramuscularly and is available in both generic and brand name forms. Common side effects of cefaloram may include diarrhea, nausea, vomiting, and allergic reactions. It should be used with caution in patients with known allergies to cephalosporins or penicillins, as well as in individuals with kidney disease.

InChI:InChI=1/C18H18N2O6S/c1-10(21)26-8-12-9-27-17-14(16(23)20(17)15(12)18(24)25)19-13(22)7-11-5-3-2-4-6-11/h2-6,14,17H,7-9H2,1H3,(H,19,22)(H,24,25)/t14-,17-/m1/s1

Upstream product

• 108260-00-0 7-aminocephalosporanic acid 
• 103-80-0 phenylacetyl chloride 
• 41128-81-8 3-Acetoxymethyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 
• 41128-81-8 (6R,7R)-benzhydryl 3-(acetyloxymethyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 
• 957-68-6 7-Aminocephalosporanic acid 
• 24144-90-9 (6R)-3-acetoxymethyl-8-oxo-7t-(2-phenoxy-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester 
• 57321-33-2 (6R)-3-acetoxymethyl-8-oxo-7t-(2-phenoxy-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 
• 108521-99-9 (R)-3-Acetoxymethyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid allyl ester 

Downstream Products

• 3595-22-0 methyl(6R,7R)-3-acetoxymethyl-7-phenylacetamidoceph-3-em-4-carboxylate 
• 3595-25-3 (6R)-3-acetoxymethyl-5ξ,8-dioxo-7t-(2-phenyl-acetylamino)-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 851-59-2 lactone of 7-phenylacetamidocephalosporanic acid 
• 7629-33-6 (6R)-3-acetoxymethyl-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid amide 
• 7629-29-0 (6R)-3-acetoxymethyl-5ξ,8-dioxo-7t-(2-phenyl-acetylamino)-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid methyl ester 
• 54240-49-2 (6R)-3-methylene-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]octane-2c-carboxylic acid 
• 53448-74-1 (6R)-3-azidomethyl-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 7629-34-7 (6R)-3-acetoxymethyl-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid cyclohexylamide 
• 6822-51-1 2-[(Z)-benzyloxycarbonyl-(2-phenyl-acetylamino)-methylene]-5-methyl-3,6-dihydro-2H-[1,3]thiazine-4-carboxylic acid 
• 41128-81-8 (6R,7R)-benzhydryl 3-(acetyloxymethyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 
• 879661-66-2 (6R)-3-acetoxymethyl-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2ξ-carboxylic acid 
• 41128-81-8 3-Acetoxymethyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 
• 37794-96-0 7-(phenylacetamido)-3-exo-methylenecepham-4-carboxylic acid 
• 27255-72-7 7-phenylacetamidodesacetoxycephalosporanic acid 

Relevant articles and documents

CEPHALOSPORIN CIPROFLOXACIN HYBRID COMPOUNDS

A compound of formula (Ia) and related aspects.

Exploitation of Antibiotic Resistance as a Novel Drug Target: Development of a β-Lactamase-Activated Antibacterial Prodrug

Expression of β-lactamase is the single most prevalent determinant of antibiotic resistance, rendering bacteria resistant to β-lactam antibiotics. In this article, we describe the development of an antibiotic prodrug that combines ciprofloxacin with a β-lactamase-cleavable motif. The prodrug is only bactericidal after activation by β-lactamase. Bactericidal activity comparable to ciprofloxacin is demonstrated against clinically relevant E. coli isolates expressing diverse β-lactamases; bactericidal activity was not observed in strains without β-lactamase. These findings demonstrate that it is possible to exploit antibiotic resistance to selectively target β-lactamase-producing bacteria using our prodrug approach, without adversely affecting bacteria that do not produce β-lactamase. This paves the way for selective targeting of drug-resistant pathogens without disrupting or selecting for resistance within the microbiota, reducing the rate of secondary infections and subsequent antibiotic use.

β-LACTAMASE TARGETED PHOTOSENSITIZER FOR PESTICIDE AND PEST DETECTION

Photoactivatable pesticide compounds and methods for the use thereof in the elimination and detection of pests are provided.