Quinupristin (mesylate)

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 . 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 . 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 .

Product information

Molecular Weight: 1118.32

Formula: C54H71N9O13S2

Chemical Name: (3S)-3-({[(3S,6S,12R,15S,16R,19S,22S,25R)-3-{[4-(dimethylamino)phenyl]methyl}-12-ethyl-15-(3-hydroxypyridine-2-amido)-4,16-dimethyl-2,5,11,14,18,21,24-heptaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaazatricyclo[20.4.0.0⁶,¹⁰]hexacosan-25-yl]methyl}sulfanyl)-1-azabicyclo[2.2.2]octan-1-ium methanesulfonate

Smiles: CN(C)C1C=CC(C[C@H]2C(=O)N3C[C@@H](CS[C@@H]4C[NH+]5CCC4CC5)C(=O)C[C@H]3C(=O)N[C@@H](C3C=CC=CC=3)C(=O)O[C@H](C)[C@H](NC(=O)C3N=CC=CC=3O)C(=O)N[C@H](CC)C(=O)N3CCC[C@H]3C(=O)N2C)=CC=1.CS([O-])(=O)=O

InChiKey: ZNQOUMVWYLNQRW-FDQSXSIVSA-N

InChi: InChI=1S/C53H67N9O10S.CH4O3S/c1-6-37-50(68)61-23-11-14-38(61)51(69)59(5)40(26-32-16-18-36(19-17-32)58(3)4)52(70)62-28-35(30-73-43-29-60-24-20-33(43)21-25-60)42(64)27-39(62)47(65)57-45(34-12-8-7-9-13-34)53(71)72-31(2)44(48(66)55-37)56-49(67)46-41(63)15-10-22-54-46;1-5(2,3)4/h7-10,12-13,15-19,22,31,33,35,37-40,43-45,63H,6,11,14,20-21,23-30H2,1-5H3,(H,55,66)(H,56,67)(H,57,65);1H3,(H,2,3,4)/t31-,35+,37-,38+,39+,40+,43-,44+,45+;/m1./s1

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

Products are for research use only. Not for human use.