Palonosetron hydrochloride

Base Information

• Chemical Name: Palonosetron hydrochloride
• CAS No.: 135729-61-2
• Deprecated CAS: 1021481-16-2
• Molecular Formula: C₁₉H₂₄N₂O
• Molecular Weight: 296.412
• European Community (EC) Number: 680-630-6
• NSC Number: 743769
• UNII: 23310D4I19
• DSSTox Substance ID: DTXSID8046610
• Wikidata: Q27158366
• NCI Thesaurus Code: C47650
• RXCUI: 397405
• ChEMBL ID: CHEMBL1720
• Mol file: 135729-61-2.mol

Synonyms:2-(1-azabicyclo(2.2.2)oct-3-yl)-2,3,3a,4,5,6-hexahydro-1H-benz(de)isoquinolin-1-one;2-QHBIQO;Aloxi;palonosetron;palonosetron hydrochloride;Palonosetron, (3R)-;palonosetron, (R-(R*,R*))-isomer;palonosetron, (R-(R*,S*))-isomer;palonosetron, (S-(R*,S*))-isomer;RS 25233 197;RS 25233 198;RS 25233-197;RS 25233-198;RS 25233197;RS 25233198;RS 25259;RS 25259 197;RS 25259 198;RS 25259-197;RS 25259-198;RS 25259197;RS 25259198;RS-25233-197;RS-25233-198;RS-25259;RS-25259-197;RS-25259-198;RS25233197;RS25233198;RS25259;RS25259197;RS25259198

Chemical Property of Palonosetron hydrochloride

Chemical Property:

• Melting Point: 87-88°
• Boiling Point: 470.414 °C at 760 mmHg
• PKA: 9.77±0.33(Predicted)
• Flash Point: 209.529 °C
• PSA: 23.55000
• Density: 1.242 g/cm³
• LogP: 3.33430
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 332.1655411
• Heavy Atom Count: 23
• Complexity: 456

Purity/Quality:

99% ^*data from raw suppliers

Palonosetron ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2CN(C(=O)C3=CC=CC(=C23)C1)C4CN5CCC4CC5.Cl
• Isomeric SMILES: C1C[C@@H]2CN(C(=O)C3=CC=CC(=C23)C1)[C@@H]4CN5CCC4CC5.Cl
• Recent ClinicalTrials: Olanzapine With or Without Fosaprepitant Dimeglumine in Preventing Chemotherapy Induced Nausea and Vomiting in Cancer Patients Receiving Highly Emetogenic Chemotherapy
• Recent EU Clinical Trials: Effects of postoperative palonosetron in ambulatory patients identified with high risk for postdischarge nausea and vomiting (PDNV) – a randomized controlled trial with comparison to placebo.
• Description: Palonosetron is a new generation 5-HT3 antagonist and It has hasgreater receptor-binding properties, which results in a much longer half-life than the previously described drugs. This selective and conformationally restricted 5-HT3 receptor antagonist was approved for the treatment of chemotherapy-induced nausea and vomiting. The drug was originally developed by Syntex Corp (now Roche Bioscience) and is currently being developed by Helsinn and MGI Pharm.
• Uses: Palonosetron is a serotonin 5-HT3 receptor antagonist used in the prevention and treatment of chemotherapy-induced nausea and vomiting (CINV). Antiemetic.
• Clinical Use: Anti-emetic: For use with cancer chemotherapy
• Drug interactions: Potentially hazardous interactions with other drugs None known

Technology Process of Palonosetron hydrochloride

There total 29 articles about Palonosetron hydrochloride 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: 96.0%

palonosetron hydrochloride (135755-51-0) → palonosetron (135729-60-1,135729-61-2,135729-73-6)

Guidance literature:

With sodium hydrogencarbonate; In water; ethyl acetate;

DOI:10.1021/acschemneuro.6b00192

Reference yield: 61.0%

(S)-2-(1-azabicyclo[2.2.2]oct-3-yl)-2,4,5,6-tetrahydro-1H-benz[de]isoquinolin-1-one (135729-56-5) → palonosetron (135729-60-1,135729-61-2,135729-73-6) + palonosetron (135729-60-1,135729-61-2,135729-73-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; for 360h;

DOI:10.1021/jm00070a008

Reference yield: 61.0%

(S)-2-(1-azabicyclo[2.2.2]oct-3-yl)-2,4,5,6-tetrahydro-1H-benz[de]isoquinolin-1-one (135729-56-5) → palonosetron (135729-60-1,135729-61-2,135729-73-6) + palonosetron (135729-60-1,135729-61-2,135729-73-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; for 360h;

DOI:10.1021/jm00070a008

upstream raw materials:

(S)-2-(1-azabicyclo[2.2.2]oct-3-yl)-2,4,5,6-tetrahydro-1H-benz[de]isoquinolin-1-one

5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid

5,6,7,8-tetrahydronaphthylene-1-carboxylic acid chloride

N-<(S)-1-azabicyclo<2.2.2>oct-3-yl>-5,6,7,8-tetrahydronaphthalene-1-carboxamide

Downstream raw materials:

palonosetron hydrochloride

palonosetron hydrochloride

Palonosetron N-oxide

Refernces

• 1、 Mu, Linjing,Müller Herde, Adrienne,Rüefli, Pascal M.,Sladojevich, Filippo,Milicevic Sephton, Selena,Kr?mer, Stefanie D.,Thompson, Andrew J.,Schibli, Roger,Ametamey, Simon M.,Lochner, Martin. "Synthesis and Pharmacological Evaluation of [11C]Granisetron and [18F]Fluoropalonosetron as PET Probes for 5-HT3 Receptor Imaging". . p. 1552 - 1564. Retrieved 2016/11/29.
• 2、 -. "PROCESSES FOR THE PREPARATION OF PALONOSETRON". . . Retrieved 2011/02/24.