Basic information Safety Supplier Related

Quinupristin

Basic information Safety Supplier Related

Quinupristin Basic information

Product Name:
Quinupristin
Synonyms:
  • 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
  • Antibiotic RP 57669
  • RP 57669
  • RP 68888
  • Quinupristin(RP-57669)
  • Quinupristin Discontinued
  • Quinupristin Mesylate
  • 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]-
CAS:
120138-50-3
MF:
C53H67N9O10S
MW:
1022.22
Product Categories:
  • Amino Acids & Derivatives
  • Aromatics
  • Chiral Reagents
  • Heterocycles
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
Mol File:
120138-50-3.mol
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Quinupristin Chemical Properties

Melting point:
~200°
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Quinupristin Usage And Synthesis

Uses

Semisynthetic depsipeptide type I streptogramin. An antibacterial agent.

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

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.

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