Quinupristin is a streptogramin antibiotic that blocks peptide bond formation and peptide extension in bacteria. Quinupristin is usually combined with another streptogramin antibiotic, dalfopristin , to produce quinupristin-dalfopristin complex , known commercially as Synercid. While both quinupristin and dalfopristin have bacteriostatic effects, they act synergistically to kill Gram-positive bacteria, as well as some Gram-negative and anaerobic bacteria.
White to off-white solid, soluble in ethanol, methanol, DMSO and water, unstable in aqueous solution.
Semisynthetic depsipeptide type I streptogramin. An antibacterial agent.
Quinupristin is a semi-synthetic analogue of virginiamycin B (ostreogrycin B, pristinamycin IA, streptogramin B) formed by a Mannich condensation and elimination to generate an exocyclic methylene alpha to the ketone of the 4-piperidinone. Addition of quinucidinylthiol to the methylene group affords quinupristin. The structural changes provide a more hydrophobic compound with a readily ionisable group for generating a salt. Quinupristin is used commercially in synergistic combination with dalfopristin (30:70). There is little published data on the synthesis, biological or antibiotic activity of quinupristin alone, however the combination product is highly effective, including activity against antibiotic resistant strains.
Quinupristin is a semi-synthetic analogue of virginiamycin B (ostreogyrcin B, pristinamycin IA, streptogramin B) formed by a Mannich condensation and elimination to generate an exocyclic methylene alpha to the ketone of the 4-piperidinone. Addition of quinucidinylthiol to the methylene group affords quinupristin. The structural changes provide a more hydrophobic compound with a readily ionisable group for generating a salt. Quinupristin is used commercially in synergistic combination with dalfopristin (30:70). There is little published data on the synthesis, biological or antibiotic activity of quinupristin alone, however the combination product is highly effective, including activity against antibiotic resistant strains.
[1] MICHAEL A. KOHANSKI James J C Daniel J Dwyer. How antibiotics kill bacteria: from targets to networks[J]. Nature Reviews Microbiology, 2010, 8 6: 423-435. DOI:
10.1038/nrmicro2333[2] JONAS NOESKE. Synergy of streptogramin antibiotics occurs independently of their effects on translation.[J]. Antimicrobial Agents and Chemotherapy, 2014: 5269-5279. DOI:
10.1128/aac.03389-14[3] WILSON D N. The A-Z of bacterial translation inhibitors.[J]. Critical Reviews in Biochemistry and Molecular Biology, 2009, 44 6: 393-433. DOI:
10.3109/10409230903307311
