Quinupristin

Quinupristin Structure
CAS No.
120138-50-3
Chemical Name:
Quinupristin
Synonyms
RP 68888;RP 57669;Antibiotic RP 57669;Quinupristin Mesylate;Quinupristin(RP-57669);Quinupristin Discontinued;Quinupristin/dalfopristin,Quinupristin,antibiotic,Quinupristin-dalfopristin,streptogramin,Inhibitor,Bacterial,inhibit;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]-
CBNumber:
CB81073487
Molecular Formula:
C53H67N9O10S
Molecular Weight:
1022.23
MOL File:
120138-50-3.mol
Modify Date:
2024/7/2 8:55:17

Quinupristin Properties

Melting point ~200°
form Solid
color White to off-white

Quinupristin Chemical Properties,Uses,Production

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.

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.

Quinupristin Preparation Products And Raw materials

Raw materials

Preparation Products

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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]- Quinupristin/dalfopristin,Quinupristin,antibiotic,Quinupristin-dalfopristin,streptogramin,Inhibitor,Bacterial,inhibit 120138-50-3 C53H67N9O10S Amino Acids & Derivatives Aromatics Chiral Reagents Heterocycles Intermediates & Fine Chemicals Pharmaceuticals