Pristinamycin

Base Information

• Chemical Name: Pristinamycin
• CAS No.: 11006-76-1
• Molecular Formula: Unspecified
• Molecular Weight: 1349.48000
• Hs Code.: 2941900000
• European Community (EC) Number: 234-244-6,686-746-3
• NSC Number: 246121
• Wikipedia: Pristinamycin,Virginiamycin
• NCI Thesaurus Code: C937,C166769
• Mol file: 11006-76-1.mol

Synonyms:Pristinamycin;Pyostacine;RP 7293;RP7293

Chemical Property of Pristinamycin

Chemical Property:

• Appearance/Colour: White solid
• Melting Point: 170-178oC
• PSA: 363.76000
• LogP: 4.99230
• Storage Temp.: Amber Vial, Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 19
• Rotatable Bond Count: 7
• Exact Mass: 1348.60159125
• Heavy Atom Count: 98
• Complexity: 2640

Purity/Quality:

50% ^*data from raw suppliers

Virginiamycin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Uses -> Pharmaceuticals
• Canonical SMILES: CCC1C(=O)N2CCCC2C(=O)N(C(C(=O)N3CCC(=O)CC3C(=O)NC(C(=O)OC(C(C(=O)N1)NC(=O)C4=C(C=CC=N4)O)C)C5=CC=CC=C5)CC6=CC=CC=C6)C.CC1C=CC(=O)NCC=CC(=CC(CC(=O)CC2=NC(=CO2)C(=O)N3CCC=C3C(=O)OC1C(C)C)O)C
• Isomeric SMILES: CCC1C(=O)N2CCCC2C(=O)N(C(C(=O)N3CCC(=O)CC3C(=O)NC(C(=O)OC(C(C(=O)N1)NC(=O)C4=C(C=CC=N4)O)C)C5=CC=CC=C5)CC6=CC=CC=C6)C.CC1/C=C\C(=O)NC/C=C\C(=C/C(CC(=O)CC2=NC(=CO2)C(=O)N3CCC=C3C(=O)OC1C(C)C)O)\C
• Recent ClinicalTrials: Study to Compare the Efficacy of Pristinamycin (Pyostacine ?) Versus Amoxicillin in the Treatment of Acute Community Acquired Pneumonia
• Recent EU Clinical Trials: ANTIBIOTIC THERAPY IN RESPIRATORY TRACT INFECTIONS: AIR.
• General Description: PRISTINAMYCIN (also known as virginiamycin) is a potent antibiotic belonging to the streptogramin class, effective against resistant bacterial strains. It consists of two synergistic components, including group A virginiamycins like virginiamycin M2, which inhibit bacterial protein synthesis. PRISTINAMYCIN's complex macrocyclic structure has been synthesized enantioselectively using advanced methodologies, highlighting its significance in antibiotic research and potential for developing novel analogues.

Refernces

Total synthesis of (-)-virginiamycin m₂: Application of crotylsilanes accessed by enantioselective Rh(II) or Cu(I) promoted carbenoid Si-H insertion

10.1021/jo202119p

The research focuses on the stereoselective synthesis of the antibiotic (?)-virginiamycin M2. The study aims to develop an efficient and enantioselective synthesis of this complex antibiotic, which is part of the group A virginiamycins known for their potent antibiotic activity against various resistant bacterial strains. The researchers employed a convergent strategy involving a series of key steps, including the use of chiral silane reagents prepared through Rh(II)- or Cu(I)-catalyzed carbenoid Si?H insertion to introduce the desired olefin geometry and stereocenters. They also utilized a modified Negishi cross-coupling or titanium-mediated alkyne?alkyne reductive coupling to assemble the trisubstituted (E,E)-diene and employed a SmI2-mediated macrocyclization to construct the 23-membered macrocycle scaffold. The synthesis was completed with a final deprotection step to reveal (?)-virginiamycin M2. The study concludes that the developed synthetic route is highly convergent, achieving the total synthesis in 19 steps with a longest linear sequence of 10 steps, and offers a modular approach that could facilitate the design and synthesis of analogues for further exploration of the biological potential of group A virginiamycins.