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Quinupristin (mesylate)

Catalog No.
C5450
streptogramin antibiotic
Grouped product items
SizePriceStock Qty
1mg
$276.00
Ship with 5-10 days
5mg
$897.00
Ship with 5-10 days

Tel: +1-832-696-8203

Email: [email protected]

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Background

Quinupristin is a streptogramin antibiotic.

Streptogramins, a class of antibiotics, are effective in the treatment of vancomycin-resistant Staphylococcus aureus and vancomycin-resistant Enterococcus, which are two of the most rapidly growing strains of multidrug-resistant bacteria. Streptogramins fall into two groups: streptogramin A and streptogramin B.

In vitro: Quinupristin can bind to sequential sites located on the 50s subunit of the bacterial ribosome. Dalfopristin binding causes a conformational change in the ribosome that subsequently increases the binding of quinupristin. The combined actions of the two agents create a stable drug-ribosome complex causing inhibition of protein synthesis by prevention of peptide-chain formation, blockade of extrusion of newly formed peptide chains, and bacterial cell death [1].

In vivo: The combination of quinupristin-dalfopristin (Q-D) and gentamicin was tested against two strains of gentamicin- and dalfopristin-susceptible methicillin-resistant Staphylococcus aureus (MRSA). A rabbit endocarditis model simulated the pharmacokinetics achieved in humans receiving intravenous injections of Q-D and gentamicin. For the MLSB-susceptible strain, a 4-day regimen reduced mean bacterial titers (MBT) in vegetations from 8.5 ± 0.8 log CFU/g (control group) to 3.0 ± 0.9 (Q-D) and 2.6 ± 0.5 log CFU/g (Q-D plus gentamicin). For the strain constitutively resistant to MLSB, a 4-day regimen reduced MBT in vegetations from 8.7 ± 0.9 log CFU/g (control group) 5.2 ± 2.2 (Q-D) and and 5.1 ± 2.4 log CFU/g (Q-D plus gentamicin). The differences between control and treatment groups were significant for both strains, although there was no significant difference between treatment groups [2].

Clinical trial: The combination quinupristin/dalfopristin (Synercid) was brought to the market by in 1999. Synercid is clinically used to treat infections by staphylococci and by vancomycin-resistant Enterococcus faecium [3].

References:
[1] Allington D R, Rivey M R Quinupristid/Dalfopristin: A Therapeutic Review.  Clinical Therapeutics .200 1, 23,(1): 24-44.
[2] Batard E, Jacqueline C, Boutoille D, Hamel A, Drugeon HB, Asseray N, Leclercq R, Caillon J, Potel G, Bugnon D.  Combination of quinupristin-dalfopristin and gentamicin against methicillin-resistant Staphylococcus aureus: experimental rabbit endocarditis study. Antimicrob Agents Chemother. 2002 Jul;46(7):2174-8.
[3] https://en. wikipedia.org/wiki/Dalfopristin

Chemical Properties

Physical AppearanceA solid
StorageStore at -20°C
M.Wt1118.3
FormulaC53H68N9O10S·CH3SO3
SynonymsRP 57669,Streptogramin B
SolubilitySoluble in ethanol;methanol;DMSO;dimethyl formamide
Chemical Name4-​[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, monomethanesulfonate
SDFDownload SDF
Canonical SMILESO=C1C[[email protected]](C(N[[email protected]@H](C2=CC=CC=C2)C(O[[email protected]](C)[[email protected]](NC(C3=C(O)C=CC=N3)=O)C4=O)=O)=O)([H])N(C([[email protected]@](CC5=CC=C(N(C)C)C=C5)([H])N(C)C([[email protected]]6([H])CCCN6C([[email protected]](N4)CC)=O)=O)=O)C[[email protected]]1CS[[email protected]@H]7C[NH+]8CCC7CC8.CS([O-])(=O)=O
Shipping ConditionEvaluation sample solution: ship with blue ice. All other available sizes: ship with RT, or blue ice upon request.
General tipsFor obtaining a higher solubility, please warm the tube at 37°C and shake it in the ultrasonic bath for a while. Stock solution can be stored below -20°C for several months.

Quality Control

Quality Control & MSDS

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Chemical structure

Quinupristin (mesylate)