Quinupristinum

Base Information

• Chemical Name: Quinupristinum
• CAS No.: 120138-50-3
• Molecular Formula: C53H67 N9 O10 S
• Molecular Weight: 1022.22
• Wikipedia: Quinupristin
• NCI Thesaurus Code: C47701
• Mol file: 120138-50-3.mol

Synonyms:5delta-(3-quinuclidinyl)thiomethylpristinamycin IA;quinupristin;RP 57669;RP-57669

Chemical Property of Quinupristinum

Chemical Property:

• Melting Point: ~200°
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 256.50000
• Density: 1.38g/cm³
• LogP: 3.12360
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 10
• Exact Mass: 1021.47316054
• Heavy Atom Count: 73
• Complexity: 2010

Purity/Quality:

99% ^*data from raw suppliers

Quinupristin >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1C(=O)N2CCCC2C(=O)N(C(C(=O)N3CC(C(=O)CC3C(=O)NC(C(=O)OC(C(C(=O)N1)NC(=O)C4=C(C=CC=N4)O)C)C5=CC=CC=C5)CSC6CN7CCC6CC7)CC8=CC=C(C=C8)N(C)C)C
• Isomeric SMILES: CC[C@H]1C(=O)N2CCC[C@H]2C(=O)N([C@H](C(=O)N3C[C@H](C(=O)CC3C(=O)N[C@H](C(=O)O[C@@H]([C@@H](C(=O)N1)NC(=O)C4=C(C=CC=N4)O)C)C5=CC=CC=C5)CS[C@@H]6CN7CCC6CC7)CC8=CC=C(C=C8)N(C)C)C
• 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: Semisynthetic depsipeptide type I streptogramin. An antibacterial agent. 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 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.