Oleandocetin

Base Information

• Chemical Name: Oleandocetin
• CAS No.: 2751-09-9
• Molecular Formula: C41H67 N O15
• Molecular Weight: 813.981
• European Community (EC) Number: 220-392-9
• Wikipedia: Troleandomycin
• NCI Thesaurus Code: C66643
• Pharos Ligand ID: 6DJ7K338QR4A
• ChEMBL ID: CHEMBL1200719
• Mol file: 2751-09-9.mol

Synonyms:Oleandocetin;TAO;Triacetyloleandomycin;Troleandomycin

Chemical Property of Oleandocetin

Chemical Property:

• Vapor Pressure: 1.82E-26mmHg at 25°C
• Melting Point: 170 °C
• Refractive Index: 1.6220 (estimate)
• Boiling Point: 812.5°Cat760mmHg
• PKA: 6.6(at 25℃)
• Flash Point: 445.2°C
• PSA: 184.19000
• Density: 1.19g/cm³
• LogP: 3.62090
• Storage Temp.: 0-6°C
• Solubility.: Soluble in DMSO (up to 50 mg/ml) or in Ethanol (up to 25 mg/ml).
• Water Solubility.: 0.25g/L(28 oC)
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 16
• Rotatable Bond Count: 12
• Exact Mass: 813.45107043
• Heavy Atom Count: 57
• Complexity: 1430

Purity/Quality:

99%, ^*data from raw suppliers

Troleandomycin 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC(C(C(O1)OC2C(CC3(CO3)C(=O)C(C(C(C(OC(=O)C(C(C2C)OC4CC(C(C(O4)C)OC(=O)C)OC)C)C)C)OC(=O)C)C)C)OC(=O)C)N(C)C
• Isomeric SMILES: C[C@@H]1C[C@@H]([C@H]([C@@H](O1)O[C@H]2[C@H](C[C@@]3(CO3)C(=O)[C@@H]([C@@H]([C@H]([C@H](OC(=O)[C@@H]([C@H]([C@@H]2C)O[C@H]4C[C@@H]([C@H]([C@@H](O4)C)OC(=O)C)OC)C)C)C)OC(=O)C)C)C)OC(=O)C)N(C)C
• Description: Troleandomycin (2751-09-9) is a macrolide antibiotic. Inhibits cytochrome P450 (IC50 = 0-5 μM), thus blocking CYP450-dependent drug oxidation.
• Uses: Troleandomycin, is a macrolide antibiotic, sold in Italy and Turkey. It is a derivative of Oleandomycin (O517500), and acts as a CYP3A4 inhibitor, which may cause drug interactions . Antibacterial.
• Clinical Use: Oleandomycin contains three hydroxyl groups that aresubject to acylation, one in each of the sugars and one in theoleandolide. The triacetyl derivative retains the in vivo antibacterialactivity of the parent antibiotic but possesses superiorpharmacokinetic properties. It is hydrolyzed in vivo tooleandomycin. Troleandomycin achieves more rapid andhigher plasma concentrations following oral administrationthan oleandomycin phosphate, and it has the additionaladvantage of being practically tasteless. Troleandomycinoccurs as a white, crystalline solid that is nearly insoluble inwater. It is relatively stable in the solid state but undergoeschemical degradation in either aqueous acidic or alkalineconditions.Because the antibacterial spectrum of activity of oleandomycinis considered inferior to that of erythromycin, thepharmacokinetics of troleandomycin have not been studiedextensively. Oral absorption is apparently good, and detectableblood levels of oleandomycin persist up to 12 hoursafter a 500-mg dose of troleandomycin. Approximately 20%is recovered in the urine, with most excreted in the feces, primarilyas a result of biliary excretion. There is some epigastricdistress following oral administration, with an incidencesimilar to that caused by erythromycin. Troleandomycin isthe most potent inhibitor of cytochrome P450 enzymes of thecommercially available macrolides. It may potentiate the hepatictoxicity of certain anti-inflammatory steroids and oralcontraceptive drugs as well as the toxic effects of theophylline,carbamazepine, and triazolam. Several allergic reactions,including cholestatic hepatitis, have also been reportedwith the use of troleandomycin.Approved medical indications for troleandomycin arecurrently limited to the treatment of upper respiratory infectionscaused by such organisms as S. pyogenes and S. pneumoniae.It may be considered an alternative to oral forms oferythromycin. It is available in capsules and as a suspension.

Technology Process of Oleandocetin

There total 1 articles about Oleandocetin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

oleandomycin (3922-90-5,7562-59-6) → troleandomycin (2751-09-9)

Guidance literature:

With pyridine; acetic anhydride;

upstream raw materials:

oleandomycin