Oritavancin
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Grundinformationen
- CAS
171099-57-3- Standard-SMILES
CN[C@H](CC(C)C)C(=O)N[C@H]1C(=O)N[C@@H](CC(N)=O)C(=O)N[C@H]2C(=O)N[C@H]3C(=O)N[C@H](C(=O)N[C@H](C(=O)O)c4cc(O)cc(O)c4-c4cc3ccc4O)[C@H](O[C@H]3C[C@](C)(N)[C@@H](O)[C@H](C)O3)c3ccc(c(Cl)c3)Oc3cc2cc(c3O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O[C@H]2C[C@](C)(NCc3ccc(-c4ccc(Cl)cc4)cc3)[C@@H](O)[C@H](C)O2)Oc2ccc(cc2Cl)[C@H]1O- InChIKey
VHFGEBVPHAGQPI-LXKZPTCJSA-N- Summenformel
- C86H97Cl3N10O26
- Durchschnittliche Molmasse
- 1.793,1 g/mol
- Monoisotopische Masse
- 1.790,56410626
Überblick
Oritavancin is a semisynthetic glycopeptide used (as its bisphosphate salt) for the treatment of acute bacterial skin and skin structure infections caused or suspected to be caused by susceptible isolates of designated Gram-positive microorganisms including MRSA. It has a role as an antimicrobial agent and an antibacterial drug. It is a glycopeptide, a disaccharide derivative and a semisynthetic derivative. It is functionally related to a vancomycin aglycone.
Namen und Bezeichner
- Bevorzugter Name
- Oritavancin
- IUPAC
- (1S,2R,18R,19R,22S,25R,28R,40S)-2-[(2R,4S,5R,6S)-4-amino-5-hydroxy-4,6-dimethyloxan-2-yl]oxy-22-(2-amino-2-oxoethyl)-5,15-dichloro-48-[(2S,3R,4S,5S,6R)-3-[(2S,4S,5R,6S)-4-[[4-(4-chlorophenyl)phenyl]methylamino]-5-hydroxy-4,6-dimethyloxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-18,32,35,37-tetrahydroxy-19-[[(2R)-4-methyl-2-(methylamino)pentanoyl]amino]-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentazaoctacyclo[26.14.2.23,6.214,17.18,12.129,33.010,25.034,39]pentaconta-3,5,8,10,12(48),14,16,29(45),30,32,34(39),35,37,46,49-pentadecaene-40-carboxylic acid
- Englischer Name
- ORITAVANCIN
- Summenformel
- C86H97Cl3N10O26
- Molmasse
- 1793.1
Namen und Synonyme
Oritavancin171099-57-3LY333328Chlorobiphenyl-chloroeremomycinLY-333328oritavancinaoritavancinePUG62FRZ2ECHEBI:82699DTXSID20897570(4''R)-22-O-(3-Amino-2,3,6-trideoxy-3-C-methyl-alpha-L-arabinohexopyranosyl)-N3''-(p-(p-chlorophenyl)benzyl)vancomycinoritavancinum
Weitere Namen anzeigen
OrbactivCS-2274Ollivan Starbrand name: OrbactivOritavancin (LY333328)Oritavancin, trifluoacetate salt13C6]-Oritavancin, trifluoacetate saltOritavancin (Lyophilized Powder For IV Infusion)
oritavacin diphosphateRefChem:57173J01XA05DTXCID701326917Oritavancin [INN]LY 333328UNII-PUG62FRZ2ECHEMBL1688530
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- XLogP
- 1,5
- Polarare Oberfläche (TPSA)
- 561 Ų
- H-Brücken-Donoren
- 20
- H-Brücken-Akzeptoren
- 29
- Frei drehbare Bindungen
- 19
- Schwere Atome
- 125
- Formalladung
- 0
- Komplexität
- 3.700
Experimentelle und physikochemische Eigenschaften
Human Drugs
Breast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Anti-Bacterial Agents; Glycopeptides; Lipoglycopeptides
EMA approved medicines: Human medicine
Dissociation Constants2.93±0.7
Physikochemische Eigenschaften
- Dichte
- 1.59 · 1.59±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- Löslichkeit
- Soluble in DMSO
- pka
- 2.93 · 2.93±0.70(Predicted)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Toxikologische Informationen
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Sicherheitsdaten
- Alarmwort
- Warnung
- Gefahrenhinweise
- Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H315
Chemie und Industrie
Pharmakologische Informationen
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
Protein BindingOritavancin is about 85% bound to plasma proteins.
Pharmacodynamics
Oritavancin interferes with bacterial cell wall synthesis and integrity, treating susceptible skin and subcutaneous tissue infections with gram-positive bacteria. This drug is known to artifically increase INR and aPTT, interfering with coagulation testing. Cases of infusion reactions have also been reported.
Mechanism of Action
The cell wall is vital for the survival and replication of bacteria, making it a primary target for antibiotic therapy. Oritavancin works against susceptible gram-positive organisms via three separate mechanisms. Firstly, it binds to the stem peptide of peptidoglycan precursors, inhibiting transglycosylation (polymerization). This process normally occurs during cell wall synthesis. Secondly, oritavancin inhibits crosslinking during bacterial cell wall biosynthesis via binding to cell wall pentaglycyl peptide bridging segments. Finally, this drug also acts by disrupting the bacterial cell membrane, interfering with its integrity, which eventually leads to cell death by various mechanisms.
Biological Half-LifeThe average terminal half-life of oritavancin is about 245 hours. A pharmacokinetic study revealed a terminal half-life ranging from 135.8-273.8 hours.
Metabolism/MetabolitesIn vitro studies on human hepatocytes suggest that oritavancin is not metabolized, and is excreted unchanged.
FDA Pharmacological Classification
PUG62FRZ2E
ORITAVANCIN
Established Pharmacologic Class [EPC] - Lipoglycopeptide Antibacterial
Chemical Structure [CS] - Lipoglycopeptides
Mechanisms of Action [MoA] - Cytochrome P450 2C19 Inhibitors
Mechanisms of Action [MoA] - Cytochrome P450 2C9 Inhibitors
Zugehörige Reaktionen
6
Notizen zur Verbindung
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