| Identification | Back Directory | [Name]
Quinupristin | [CAS]
120138-50-3 | [Synonyms]
RP 57669
RP 68888
Antibiotic RP 57669
Quinupristin Mesylate
Quinupristin(RP-57669)
Quinupristin
Discontinued
4-[4-(DiMethylaMino)-N-Methyl-L-phenylalanine]-5-[(2S,5R)-5-[[[(3S)-1-azabicyclo[2.2.2]oct-3-yl]thio]Methyl]-4-oxo-2-piperidinecarboxylic acid]virginiaMycin S1
Virginiamycin S1, 4-[4-(dimethylamino)-N-methyl-L-phenylalanine]-5-[(2S,5R)-5-[[[(3S)-1-azabicyclo[2.2.2]oct-3-yl]thio]methyl]-4-oxo-2-piperidinecarboxylic acid]- | [Molecular Formula]
C53H67N9O10S | [MDL Number]
MFCD00865105 | [MOL File]
120138-50-3.mol | [Molecular Weight]
1022.23 |
| Hazard Information | Back Directory | [Description]
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. | [Chemical Properties]
White to off-white solid, soluble in ethanol, methanol, DMSO and water, unstable in aqueous solution. | [Uses]
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. | [Uses]
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. | [Uses]
Semisynthetic depsipeptide type I streptogramin. An antibacterial agent. | [References]
[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 |
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