Quinupristin
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Grundinformationen
- CAS
120138-50-3- Standard-SMILES
CC[C@H]1NC(=O)[C@@H](NC(=O)c2ncccc2O)[C@@H](C)OC(=O)[C@H](c2ccccc2)NC(=O)[C@@H]2CC(=O)[C@H](CS[C@@H]3CN4CCC3CC4)CN2C(=O)[C@H](Cc2ccc(N(C)C)cc2)N(C)C(=O)[C@H]2CCCN2C1=O- InChIKey
WTHRRGMBUAHGNI-KNIYECGFSA-N- Summenformel
- C53H67N9O10S
- Durchschnittliche Molmasse
- 1.022,239 g/mol
- Monoisotopische Masse
- 1.021,47316034
Namen und Bezeichner
- Bevorzugter Name
- Quinupristin
- IUPAC
- N-[(6R,9S,10R,13S,15aS,18R,22S,24aR)-18-({[(3S)-1-Azabicyclo[2.2.2]octan-3-yl]sulfanyl}methyl)-22-{[4-(dimethylamino)phenyl]methyl}-6-ethyl-10,23-dimethyl-5,8,12,15,17,21,24-heptaoxo-13-phenyldocosahydro-12H-pyrido[2,1-f]pyrrolo[2,1-l][1,4,7,10,13,16]oxapentaazacyclononadecin-9-yl]-3-hydroxypyridine-2-carboxamide
- Englischer Name
- Quinupristin
- Summenformel
- C53H67N9O10S
- Molmasse
- 1022.22
Namen und Synonyme
RP 68888RP 57669Antibiotic RP 57669Quinupristin MesylateQuinupristin(RP-57669)Quinupristin DiscontinuedQuinupristin/dalfopristin,Quinupristin,antibiotic,Quinupristin-dalfopristin,streptogramin,Inhibitor,Bacterial,inhibit4-[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 S1Virginiamycin 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]-N-(3-Hydroxy-2-pyridylcarbonyl)-(S)-threonyl-(R)-(alpha-aminobutyryl)-(S)-prolyl-[N-methyl-4-(dimethylamino)-(S)-phenylalanyl]-[4-oxo-5(R)-[quinuclidin-3(S)-ylthiomethyl]-(S)-homoprolyl]-(S)-phenylglycine C-1.6-O-3.1-lactone
Datenbank-Bezeichner
- CAS
120138-50-3- PubChem CID
- 165367985
- DTXSID
DTXSID00873377
Eigenschaften
Physikochemische Eigenschaften
- Schmelzpunkt
- 200 ° · ~200°
- Dichte
- 1.388 · 1.388±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)
- Löslichkeit
- DMF: SolubleDMSO: SolubleEthanol: SolubleMethanol: Soluble
- pka
- 3.519 · 3.519±0.35(predicted)
- Aggregatzustand
- Solid
- Farbe
- White to off-white
- Henry's Law Constant
- 4.9 · 4.9×1022 mol/(m3Pa) at 25℃, HSDB (2015)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Sicherheitsdaten
- Giftige Stoffe Daten
- 120138-50-3(Hazardous Substances Data)
Chemie und Industrie
Anwendungen
BeschreibungQuinupristin 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.
VerwendenQuinupristin 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.
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