859-07-4

Usage

Uses

Used in Medical Industry:
Cefaloram is used as an antibiotic for treating various bacterial infections such as respiratory tract, urinary tract, skin, and soft tissue infections. Its mechanism of action involves inhibiting the synthesis of the bacterial cell wall, which results in the disruption of the bacterial cell membrane and the death of the bacteria.
Cefaloram is typically administered intravenously or intramuscularly and is available in both generic and brand name forms. It should be used with caution in patients with known allergies to cephalosporins or penicillins, as well as in individuals with kidney disease. Common side effects of cefaloram may include diarrhea, nausea, vomiting, and allergic reactions.

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

• 957-68-6 7-Aminocephalosporanic acid 
• 103-80-0 phenylacetyl chloride 
• 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 
• 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 
• 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 
• 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 
• 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 
• 108260-00-0 7-aminocephalosporanic acid 

Downstream Products

• 6822-51-1 2-[(Z)-benzyloxycarbonyl-(2-phenyl-acetylamino)-methylene]-5-methyl-3,6-dihydro-2H-[1,3]thiazine-4-carboxylic acid 
• 3595-22-0 methyl(6R,7R)-3-acetoxymethyl-7-phenylacetamidoceph-3-em-4-carboxylate 
• 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 
• 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 
• 28240-15-5 3-hydroxymethyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 347193-74-2 Acetic acid (6R,7R)-2-chlorocarbonyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl ester 
• 102779-37-3 (7R,7aR)-3-[(acetyloxy)methyl]-1,6-dioxo-7-[(2-phenylacetyl)amino]-1,6,7,7a-tetrahydro-2H-1λ⁴-azeto[2,1-b][1,3]thiazine-4-carboxylic acid 
• 805-64-1 (6R)-3-acetoxymethyl-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2ξ-carboxylic acid 
• 347193-86-6 4-Fluoro-benzoic acid (6R,7R)-3-acetoxymethyl-7-tert-butoxycarbonylamino-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-2-ylmethyl ester 
• 347193-76-4 N-((6R)-3-acetoxymethyl-2-benzoyloxymethyl-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-7t-yl)-2-phenyl-acetamide 
• 347193-82-2 N-((6R)-3-acetoxymethyl-2-(4-fluorobenzoyl)oxymethyl-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-7t-yl)-2-phenyl-acetamide 
• 347193-85-5 2,2-Dimethyl-propionic acid (6R,7R)-3-acetoxymethyl-7-(tert-butoxycarbonyl-phenylacetyl-amino)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-2-ylmethyl ester 
• 347193-77-5 Benzoic acid (6R,7R)-3-acetoxymethyl-7-(tert-butoxycarbonyl-phenylacetyl-amino)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-2-ylmethyl ester 
• 347193-84-4 4-Fluoro-benzoic acid (6R,7R)-3-acetoxymethyl-7-(tert-butoxycarbonyl-phenylacetyl-amino)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-2-ylmethyl ester 

Relevant academic research and scientific papers

CEPHALOSPORIN CIPROFLOXACIN HYBRID COMPOUNDS

A compound of formula (Ia) and related aspects.

PRODRUG INHIBITORS

Provided herein are compounds useful as metallo-β-lactamase (MBL) inhibitors. The compounds have a formula A–B, where A is a β-lactam antibiotic moiety comprising a bridging methylene (-CH2-) covalently attached to -B; and B is a latent MBL inhibitor. Also provided are formulations comprising such compounds; as well as such compounds or formulations for use as a medicament. The compounds and formulations may be used in the treatment of antibiotic resistance, bacterial infection. The compounds and formulations may be used in the inhibition of a bacterial MBL.

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.

Studies at the ionizable position of cephalosporins and penicillins: Hydroxamates as substitutes for the traditional carboxylate group

Classically, β-lactams need an ionizable group to potentiate antibacterial activity. Sets of cephalosporins and penicillins featuring different substituted hydroxamates in place of the traditional carboxylate group have been synthesized and tested for antibiotic activity. Many of the compounds exhibited anti-bacterial activities with notable MIC values in the range of 6-0.2 μM.

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.

CEPHALOSPORIN DERIVATIVES USEFUL AS β-LACTAMASE INHIBITORS AND COMPOSITIONS AND METHODS OF USE THEREOF

The present invention relates to cephalosporin derivatives having β- lactamase inhibitory activity. The compounds are useful in preventing or treating bacterial resistance to an antibiotic, e.g. a β-lactam antibiotic. Disclosed herein are compounds that are inhibitors of class B metallo-β-lactamases, as well as class A, C, and D serine β-lactamases. In some preferred embodiments, the compounds are 3'- thiobenzoate derivatives of a cephalosporin. Pharmaceutical compositions, methods, uses, kits and commercial packages comprising the compounds are also disclosed.

PHOTOACTIVATABLE ANTIMICROBIAL AGENTS AND THERAPEUTIC AND DIAGNOSTIC METHODS OF USING SAME

The present invention provides photosensitizer compounds for use in detecting beta-lactamase activity. Methods and kits that utilize the photosensitizer compounds of the invention for the detection of, quantitation of, and classification or typing of microbial beta-lactamases.

Enzymatic deprotection of the cephalosporin 3′-acetoxy group using Candida antarctica lipase B

(Chemical Equation Presented) Cephalosporins remain one of themost important classes of antibiotics. A useful site for derivatization involves generation of and chemistry at the 3′-hydroxymethyl position. While 3′-acetoxymethyl-substituted cephalosporins are readily available, deacetylation to access the free 30-hydroxymethyl group is problematic when the carboxylic acid is protected as an ester. Herein we report that this important transformation has been efficiently accomplished using Candida antarctica lipase B. Although this transformation is difficult to carry out using chemical methods, the enzymatic deacetylation has been successful on gram scale, when the cephalosporin is protected as either the benzhydryl or tert-butyl esters and on the corresponding sulfoxide and sulfone of the tert-butyl ester.

An improved process for the preparation of diphenylmethyl7β- Phenylacetamido-3-hydroxymethyl-3-cephem-4-carboxylate

An efficient and improved process for the preparation of diphenylmethyl 7-phenylacetamido-3-hydroxymethyl-3-cephem-4-carboxylate was developed. With the commercially available 7-aminocephalosporanic acid (7-ACA) as starting material, up to 73.5% overall isolated yield of the titled compound was synthesized in two steps via direct phenylacetylation with phenylacetyl chloride, followed by basic hydrolysis and esterification with diphenyldiazomethane. The newly developed process obviated the use of protecting groups, reduced the environmental footprint, and could be easily controlled and conveniently scaled up for this pivotal intermediate in cephalosporin chemistry.

PHOTOACTIVATABLE ANTIMICROBIAL AGENTS

Photoactivatable antimicrobial compounds and methods for the use thereof in the treatment of infections are provided.