C86H97Cl3N10O26
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
- 1.790,564106
Überblick
Oritavancin is a glycopeptide antibiotic used for the treatment of skin infections. It was developed by The Medicines Company (acquired by Novartis). Oritavancin was initially approved by the FDA in 2014 and formulated to combat susceptible gram-positive bacteria that cause skin and skin structure infections. It boasts the option of single-dose administration and has been proven as non-inferior to a full course of [vancomycin] therapy. On March 12, 2021 the FDA approved Kimyrsa, a complete course of therapy in a single, 1 hour 1200 mg infusion. Orbactiv, the other FDA approved oritavancin product, is administered over a 3 hour infusion and contains a lower dose of 400 mg. Marketed by Melinta Therapeutics, Kimyrsa offers effective and time-efficient treatment for skin and skin structure infections.
Namen und Bezeichner
- Bevorzugter Name
- C86H97Cl3N10O26
- IUPAC
- (1S,2R,18R,19R,22S,25R,28R,40S)-2-[(2R,4S,5R,6S)-4-amino-5-hydroxy-4,6-dimethyloxan-2-yl]oxy-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-18,20,23,26,32,35,37,42,44-nonahydroxy-22-(2-hydroxy-2-iminoethyl)-19-[[(2R)-1-hydroxy-4-methyl-2-(methylamino)pentylidene]amino]-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),14,16,20,23,26,29(45),30,32,34(39),35,37,41,43,46,49-icosaene-40-carboxylic acid
- Englischer Name
- ORITAVANCIN
- Summenformel
- C86H97Cl3N10O26
- Molmasse
- 1793.1
Namen und Synonyme
C86H97Cl3N10O26OrbactivCS-2274LY 333328ORITAVANCINOllivan Starbrand name: OrbactivOritavancin (LY333328)Oritavancin, trifluoacetate salt13C6]-Oritavancin, trifluoacetate saltOritavancin (Lyophilized Powder For IV Infusion)
Datenbank-Bezeichner
- CAS
171099-57-3- PubChem CID
- 101991076
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 4,4
- Polarare Oberfläche (TPSA)
- 583 Ų
- H-Brücken-Donoren
- 21
- H-Brücken-Akzeptoren
- 36
- Frei drehbare Bindungen
- 19
- Schwere Atome
- 125
- Formalladung
- 0
- Komplexität
- 3.800
Experimentelle und physikochemische Eigenschaften
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.
Sicherheitsdaten
- Alarmwort
- Warnung
- Gefahrenhinweise
- Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H315
Chemie und Industrie
Pharmakologische Informationen
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.
Absorption, Distribution and Excretion
Pharmacokinetic analysis of oritavancin revealed a Cmax of 138 and μg/mL and an AUC0-∞ of 2800 μg•h/mL. The AUC0-t in a study of healthy volunteers after an 800 mg dose 1,1111 μg•h/mL. was also be Another pharmacokinetic study reported a Cmax of 4.7-7.6 micrograms/mL, generally achieved within 24 hours of administration.
Oritavancin is excreted as unchanged drug in both the urine and feces. Less than 5% has been recovered in the urine, and 1% has been recovered in the feces.
The volume of distribution of oritavancin is estimated at 87.6 L, suggesting extensive tissue distribution.
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