Oritavancin

Oritavancin (LY 333328), a semisynthetic derivative of Vancomycin (HY-B0671), is an orally active glycopeptide antibiotic with bactericidal activity against gram-positive organisms. Oritavancin shows antibacterial effect against B. anthracis, such as Ames strain with a MIC value of 0.015 g/mL. Oritavancin inhibits cell wall synthesis and disrupts the membrane potential. Oritavancin inhibits ArlS kinase activity thereby interfering the signal transduction. Oritavancin enters cells by adsorptive endocytosis, which drives it to lysosomes, where it exerts antibiotic activity[1][2][3][4][5].

Product Specifications

CAS Number

[171099-57-3]

Product Name Alternative

LY 333328; Orbactiv

UNSPSC

12352005

Target

Antibiotic; Bacterial

Type

Reference compound

Related Pathways

Anti-infection

Applications

COVID-19-immunoregulation

Field of Research

Infection; Inflammation/Immunology

Assay Protocol

https://www.medchemexpress.com/oritavancin.html

Solubility

10 mM in DMSO

Smiles

O[C@@H]1[C@@H](O[C@@](O[C@@H](C)[C@@H]2O)([H])C[C@]2(C)NCC3=CC=C(C4=CC=C(Cl)C=C4)C=C3)[C@@H](O[C@H](CO)[C@H]1O)OC5=C(OC6=CC=C([C@H]([C@H]7NC([C@H](NC)CC(C)C)=O)O)C=C6Cl)C=C([C@](NC([C@@H](NC7=O)CC(N)=O)=O)([H])C(N[C@](C8=O)([H])C9=CC%10=C(O)C=C9)=O)C=C5OC%11=CC=C([C@H]([C@](C(N[C@@](C(O)=O)([H])C%12=C%10C(O)=CC(O)=C%12)=O)([H])N8)O[C@@](O[C@@H](C)[C@@H]%13O)([H])C[C@@]%13(N)C)C=C%11Cl

Molecular Formula

C86H97Cl3N10O26

Molecular Weight

1793.10

References & Citations

[1]Coyle EA, et al. Activity of oritavancin (LY333328), an investigational glycopeptide, compared to that of vancomycin against multidrug-resistant Streptococcus pneumoniae in an in vitro pharmacodynamic model. Antimicrob Agents Chemother. 2001 Mar;45 (3) :706-9.|[2]Arhin FF, et al. Effect of polysorbate 80 on oritavancin binding to plastic surfaces: implications for susceptibility testing. Antimicrob Agents Chemother. 2008 May;52 (5) :1597-603. |[3]Bai J, et al. The role of ArlRS in regulating oxacillin susceptibility in methicillin-resistant Staphylococcus aureus indicates it is a potential target for antimicrobial resistance breakers[J]. Emerg Microbes Infect. 2019;8 (1) :503-515.|[4]Van Bambeke F, et al. Cellular pharmacokinetics and pharmacodynamics of the glycopeptide antibiotic oritavancin (LY333328) in a model of J774 mouse macrophages[J]. Antimicrob Agents Chemother. 2004 Aug;48 (8) :2853-60.|[5]Heine HS, et al. Efficacy of oritavancin in a murine model of Bacillus anthracis spore inhalation anthrax. Antimicrob Agents Chemother. 2008 Sep;52 (9) :3350-7.