Moxalactam Sodium (syn: Latamoxef Sodium) is a an oxacephem antibiotic usually grouped with the cephalosporins. In oxacephems such as these, the sulfur atom of the cephalosporin core is replaced with an oxygen atom. It is derived from 7-aminocephalosporanic acid. Moxalactam Sodium is used in forensics and toxicology applications and in vitro veterinary research. It is also used in susceptibility testing applications. Moxalactam Sodium can also be used in plant biotechnology applications for contamination control after Agrobacterium-mediated transformation protocols.
Moxalactam Sodium is freely soluble in water.
| Mechanism of Action | Like β-lactams, cephalosporins interfere with PBP (penicillin binding protein; primarily PBP 3 and PBP 1b) activity involved in the final phase of peptidoglycan synthesis. PBP’s are enzymes which catalyze a pentaglycine crosslink between alanine and lysine residues providing additional strength to the cell wall. Without a pentaglycine crosslink, the integrity of the cell wall is severely compromised and ultimately leads to cell lysis and death. Resistance to cephalosporins is commonly due to cells containing plasmid encoded β-lactamases. Latamoxef works by inhibiting bacterial cell wall biosynthesis. |
| Spectrum |
Moxalactam has a broad spectrum of activity against Gram-positive and Gram-negative aerobic and anaerobic bacteria, is particularly active against Enterobacteriaceae and is resistant to hydrolysis by beta-lactamases. Moxalactam has moderate activity against Pseudomonas aeruginosa, but on the basis of present evidence cannot be recommended as sole antibiotic treatment of known or suspected pseudomonal infections. Moxalactam is primarily indicated for bacteria causing bone and joint infection, GI infections, gynecological infections, meningitis, respiratory tract infections, septicaemia, skin infections, soft tissue infections, urinary tract infections. Moxalactam is ineffective against methicillin-resistant S. aureus (MRSA) and Enterococci. |
| Microbiology Applications | Moxalactam Sodium is commonly used in clinical in vitro microbiological antimicrobial susceptibility tests (agar diffusion assay) against Gram-negative microbial isolates. Medical microbiologists use AST results to recommend antibiotic treatment options. Representative MIC values include:
Moxalactam is used as a media supplement in Oxford Listeria agar to select for Listeria monocytogenes in poultry and processed meats. |
| Plant Biology Applications | Researchers used moxalactam for Agrobacterium-mediated transformation of tobacco, tomato and rice in comparison with carbenicillin and cefotaxime. When used at a concentration of 6.25–50 mg/L, this resulted in a higher transformation efficiency compared to carbenicilin and cefotaxime. In general, the activity of the antimicrobial used for this purpose depends on the Agrobacterium strain, binary vector, plant species, type of explants, medium, selective agent used and its concentration (Ogawa et al, 2007). |
| Cancer Applications |
Moxalactam can be used for breast cancer research. Researchers designed and developed a Förster resonance energy transfer (FRET) based biosensor for rapid in vitro high-throughput screening of potential inhibitors of the hNTH1–YB1 complex. This complex is a druggable target for the development of strategies for drug-resistant tumors. This biosensor can be used to screen inhibitors of therapeutically relevant protein–protein interfaces (Senarisoy et al, 2020). Moxalactam is considered as a potential inhibitor of Human lactate dehydrogenase A (LDHA) and can be used for cancer research studies. A pharmacophore-based screening method revealed Moxalactam is an LDHA inhibitor. This anaerobic glycolytic enzyme is involved in the inter-conversion of pyruvate to lactate. The level of LDHA in various types of cancer cells is found to be elevated and authors concluded Moxalactam merits further study for this application (2020). |
| Molecular Formula | C20H18N6O9S · 2Na |
| Optical Rotation | [α]D22 = -45° (water) |
| References |
Carmine AA et al (1983) Moxalactam (latamoxef). A review of its antibacterial activity, pharmacokinetic properties and therapeutic use. Drugs. 1983 26(4):279-333 PMID 6354685 Georgopapadakou NH (1992) Mechanisms of action of Cephalosporin 3'-quinolone esters, carbamates, and tertiary amines in Escherichia coli. Antimicrob. Agents and Chemother. 37(3):559-565 Neu HC (1982) The in vitro activity, human pharmacology, and clinical effectiveness of new β-lactam antibiotics. Annu. Rev. Pharmacol. Toxicol. 22:599-642 Paul SK et al (2023) Exploring the possibility of drug repurposing for cancer therapy targeting human lactate dehydrogenase A: A computational approach. J. Biomol. Struct. Dyn. 41(19):9967-9976 PMID 36576127 Senarisoy M et al (2020) Förster resonance energy transfer based biosensor for targeting the hNTH1–YB1 interface as a potential anticancer drug target. ACS Chem. Biol. 15 (4):990-1003 Yoichi Ogawa Y and Masahiro M (2007) Meropenem and moxalactam: Novel β-lactam antibiotics for efficient Agrobacterium-mediated transformation. Plant Sci. 172(3):564-572 |
| MIC | Bacteroides disiens| 0.5 － 16|| Bacteroides distasonis| 1 － >128|| Bacteroides fragilis| 0.25 － 256|| Bacteroides melaninogenicus| 0.125 － 16|| Bacteroides oralis | 0.25 － 32|| Bacteroides ovatus| 1 － >128|| Bacteroides putredinis| ≤0.062|| Bacteroides ruminicola | 0.5|| Bacteroides ruminicola subsp. brevis| 0.5 － 128|| Bacteroides thetaiotaomicron| 0.5 － 256|| Bacteroides uniformis| 0.5 － 128|| Bacteroides ureolyticus| 0.125 － 2|| Bacteroides vulgatus| 1 － 16|| Bifidobacterium spp.| 1 － >128|| Brucella| 1 － 16|| Citrobacter diversus| 0.12 － 0.5|| Citrobacter freundii| 0.06 － 8|| Clostridium bifermentans| 0.5 － 8|| Clostridium cadaveris| 0.5 － 8|| Clostridium difficile| 2 － 128|| Clostridium perfringens| 0.5 － >64|| Clostridium ramosum| 8|| Clostridium sordellii| 0.5 － 8|| Clostridium spp.| 0.5 － >64|| Clostridium tertium| 0.5 － 8|| Enterobacter aerogenes| 0.25 - 4|| Enterobacter agglomerans| 0.25 - 4|| Enterobacter cloacae| 0.06 － 4|| Enterobacter gergoviae| 0.25 - 4|| Escherichia coli| 0.015 － 2|| Eubacterium lentum| 1 － >128|| Eubacterium spp.| 0.5 － 4|| Flavobacterium (IIb)| 0.25 － 32|| Fusobacteria| 0.125 － 16|| Fusobacterium mortiferum| 4 － 16|| Fusobacterium necrophorum| 0.125 － 0.25|| Fusobacterium nucleatum| 1 － 4|| Fusobacterium varium| 4 － 16|| Haemophilus influenzae| 0.03 - 0.12|| Helicobacter pylori| 0.05 － 1.56|| Klebsiella pneumonia| 0.015 － 64|| Klebsiella pneumoniae| 0.12 - 0.25|| Lactobacillus spp.| 1 － >128|| Leptotrichia buccalis| 0.5|| Moraxella osloensis | 0.12 － 16|| Morganella morganii| 0.12 － 0.5|| Neisseria gonorrhoeae| ≤0.008 - 0.6|| Neisseria meningitidis| ≤0.008|| Nocardia asteroides| 17.96|| Peptococcus asaccharolyticus| 0.25 － 2|| Peptococcus magnus | 0.125 － 2|| Peptostreptococcus anaerobius| 0.06 － 16|| Peptostreptococcus asaccharolyticus| 0.06 － 16|| Peptostreptococcus magnus| 0.06 － 16|| Peptostreptococcus micros| ≤0.062 － 0.25|| Peptostreptococcus prevotii| ≤0.062 － 2|| Peptostreptococcus tetradius| 0.06 － 16|| Porphyromonas| 0.125 － 64|| Porphyromonas asaccharolytica| 0.125 － 64|| Prevotella bivia| 0.25 － 32|| Prevotella buccae| 0.125 － 64|| Prevotella corporis | 0.5 － 4|| Prevotella disiens| 0.5 － 64|| Prevotella intermedia| 0.5 － 16|| Prevotella melaninogenica| 0.5 － 16|| Prevotella oralis| 0.125 － 64|| Prevotella oris| 0.125 － 64|| Propionibacterium acnes| 1 － 2|| Propionibacterium spp.| 1 － 2|| Proteus mirabilis| 0.25|| Proteus vulgaris| 0.12 - 0.5|| Providencia rettgeri| 0.25 - 0.5|| Providencia stuartii| 0.25 - 0.5|| Pseudomonas acidovorans| 0.12 － 4|| Pseudomonas aeruginosa| 4 － 512|| Pseudomonas cepacia| 2 － 256|| Pseudomonas fluorescens | 0.12 － 256|| Pseudomonas maltophilia| 2 － 256|| Pseudomonas putida| 16 － 256|| Pseudomonas putrefaciens| 0.5 － 2|| Pseudomonas stutzeri| 0.5 － 8|| Ralstonia pickettii| 8|| Serratia marcescens| 0.5 - 512|| Staphylococcus aureus| 3.12 － 256|| Streptococcus faecalis| >256|| Streptococcus pneumoniae| 1|| Streptococcus pyogenes| 1 － 2|| |
