Eravacycline Dihydrochloride is the dihydrochloride salt of Eravacycline, a third-generation tetracycline antibiotic with broad-spectrum activity. It is a derivative of tetracycline that has additional fluorine atoms, a fluorocycline (syn: 7-fluoro-9-pyrrolidinoacetamido-6-demethyl-6-deoxytetracycline). It was developed by Tetraphase Pharmaceuticals and was approved by the FDA in 2018.
Eravacycline DiHCl is soluble in water.
| Mechanism of Action |
Tetracycline antibiotics inhibit bacterial growth by disrupting codon-anticodon interactions at the ribosome, thus blocking protein synthesis. Specifically, they bind to a single site on the 30S ribosomal subunit and inhibit protein synthesis by blocking the attachment of charged aminoacyl-tRNA to the A site on the ribosome. Thus, they prevent introduction of new amino acids to the nascent peptide chain. The compound has antibacterial properties against multidrug resistant (MDR) Gram-positive and Gram-negative isolates. Eravacycline was designed to overcome resistance to common tetracycline-specific efflux and ribosomal protection mechanisms via its unique chemical modifications at C-9 and C-7 of the tetracycline core. It maintains high binding affinity to the bacterial ribosome even in presence of ribosomal protection proteins (RPPs). |
| Spectrum |
Broad-spectrum activity against both Gram-positive and Gram-negative bacteria, both aerobic and anaerobic pathogens including the Gram-positive methicillin-resistant Staphylococcus aureus (MRSA). It is active against multidrug-resistant bacteria including those expressing extended-spectrum beta-lactamases. |
| Microbiology Applications |
Eravacycline had potent broad-spectrum activity against 90% of the isolates (MIC90) in panels of all major bacterial species (aerobic, anaerobic, Gram-negative, Gram-positive for a total of 2644 isolates including clinical isolates) and MIC90s were <= 2 ug/ml with the exception of Pseudomonas aeruginosa and Burkholderia cenocepacia (Sutcliffe et al, 2013). MIC values were determined by microtiter microdilution broth (aerobic) or agar dilution (anaerobic) methods. |
| Molecular Formula | C27H31FN4O8 X 2HCl |
| References |
Jabarin A et al (2024) Eravacycline, an antibacterial drug, repurposed for pancreatic cancer therapy: Insights from a molecular-based deep learning model. Briefings in Bioinformatics 25(3): bbae108 Seifert H, Stefanik D, Sutcliffe JA, Higgins PG (2018) In-vitro activity of the novel fluorocycline Eravacycline against carbapenem non-susceptible Acinetobacter baumannii. Int. J. Antimicrob. Agents. 51(1):62-64 PMID 28705668 Sutcliffe JA, O'Brien W, Fyfe C, Grossman TH (2013) Antibacterial activity of Eravacycline (TP-434), a novel fluorocycline, against hospital and community pathogens. Antimicrob. Agents Chemother. 57(11):5548-5558 PMID 23979750 Xiao XY et al (2012) Fluorocyclines. 1. 7-fluoro-9-pyrrolidinoacetamido-6-demethyl-6-deoxytetracycline: a potent, broad spectrum antibacterial agent. J Med. Chem. 55(2):597-605 PMID 22148514 Varghese D, Sunny D, Kurian A, Cherian T, Varghese L (2023) An in silico study on reproposing eravacycline as an MMP inhibitor. J. Appl. Pharm. Sci. 13(01):232–240 |
