Oritavancin is an antibiotic used to treat skin and skin structure infections, belonging to the class of glycopeptide antibiotics.
CAT No: R2239
CAS No:171099-57-3
Synonyms/Alias:LY333328; LY 333328; LY-333328
Chemical Name:(1S,2R,18R,19R,22S,25R,28R,40S)-2-[(2R,4S,5R,6S)-4-amino-5-hydroxy-4,6-dimethyloxan-2-yl]oxy-22-(2-amino-2-oxoethyl)-5,15-dichloro-48-[(2S,3R,4S,5S,6R)-3-[(2S,4S,5R,6S)-4-[[4-(4-chlorophenyl)phenyl]methylamino]-5-hydroxy-4,6-dimethyloxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-18,32,35,37-tetrahydroxy-19-[[(2R)-4-methyl-2-(methylamino)pentanoyl]amino]-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentazaoctacyclo[26.14.2.23,6.214,17.18,12.129,33.010,25.034,39]pentaconta-3,5,8,10,12(48),14,16,29(45),30,32,34(39),35,37,46,49-pentadecaene-40-carboxylic acid
Oritavancin is a semi-synthetic glycopeptide antibiotic that exhibits potent activity against a broad spectrum of Gram-positive bacteria, including resistant strains such as methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant enterococci (VRE). Structurally derived from the natural glycopeptide chloroeremomycin, oritavancin features unique lipophilic side chains and additional modifications that enhance its antimicrobial efficacy and pharmacokinetic properties. Its complex mode of action involves inhibition of cell wall biosynthesis and disruption of membrane integrity, making it a valuable molecular tool in the study of bacterial physiology and resistance mechanisms. Due to its distinctive biochemical properties, oritavancin is widely utilized in microbiological research, antimicrobial development, and mechanistic studies focused on combating drug-resistant pathogens.
Antimicrobial resistance research: Oritavancin serves as a critical reagent in studies aimed at elucidating mechanisms of resistance in Gram-positive bacteria. Researchers employ it to investigate how modifications in cell wall structure or membrane composition contribute to decreased susceptibility, providing valuable insights into the evolution of resistance phenotypes. These investigations help identify genetic and biochemical factors that influence glycopeptide efficacy, supporting the development of next-generation antimicrobials and resistance mitigation strategies.
Microbial susceptibility testing: In microbiology laboratories, oritavancin is routinely used as a reference compound for antimicrobial susceptibility assays. Its well-characterized activity profile enables accurate benchmarking of bacterial isolates, particularly those exhibiting multi-drug resistance. Such testing is essential for validating new diagnostic methods, monitoring trends in resistance, and calibrating laboratory protocols for the detection of glycopeptide-resistant organisms.
Mode of action studies: The compound's multifaceted mechanism, which includes inhibition of transglycosylation and transpeptidation as well as membrane depolarization, makes it an important probe for dissecting bacterial cell wall synthesis pathways. By applying oritavancin in biochemical assays, researchers can delineate the specific molecular targets and interactions responsible for its bactericidal effects. These studies contribute to a deeper understanding of cell envelope biogenesis and inform the rational design of structurally related agents.
Analytical method development: Oritavancin is frequently utilized as a standard or control in the development and validation of analytical techniques for glycopeptide quantification. Its unique chemical structure and stability facilitate the optimization of chromatographic and mass spectrometric protocols, ensuring accurate detection in complex biological matrices. Such methods are vital for pharmacokinetic research, quality control, and the assessment of compound distribution in experimental models.
Antibiotic synergy investigations: The compound is also employed in combination studies to assess potential synergistic or antagonistic interactions with other antimicrobial agents. These experiments are designed to evaluate the effects of co-administration on bacterial growth inhibition, cell wall integrity, and resistance emergence. Insights gained from such synergy testing inform combination therapy strategies and support the identification of novel drug pairings with enhanced efficacy against recalcitrant pathogens.
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