Palonosetron (CHEM022102)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:20:04 UTC
Update Date2016-11-09 01:17:25 UTC
Accession NumberCHEM022102
Identification
Common NamePalonosetron
ClassSmall Molecule
DescriptionPalonosetron (INN, trade name Aloxi) is a 5-HT3 antagonist used in the prevention and treatment of chemotherapy-induced nausea and vomiting (CINV). It is the most effective of the 5-HT3 antagonists in controlling delayed CINV nausea and vomiting that appear more than 24 hours after the first dose of a course of chemotherapy and is the only drug of its class approved for this use by the U.S. Food and Drug Administration. As of 2008, it is the most recent 5-HT3 antagonist to enter clinical use.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-QHBIQOHMDB
Palonosetron, (R-(r*,s*))-isomerHMDB
Palonosetron, (S-(r*,s*))-isomerHMDB
Palonosetron hydrochlorideHMDB
2-(1-Azabicyclo(2.2.2)oct-3-yl)-2,3,3a,4,5,6-hexahydro-1H-benz(de)isoquinolin-1-oneHMDB
AloxiHMDB
Palonosetron, (R-(r*,r*))-isomerHMDB
Chemical FormulaC19H24N2O
Average Molecular Mass296.407 g/mol
Monoisotopic Mass296.189 g/mol
CAS Registry Number119904-90-4
IUPAC Name(5R)-3-[(3S)-1-azabicyclo[2.2.2]octan-3-yl]-3-azatricyclo[7.3.1.0⁵,¹³]trideca-1(12),9(13),10-trien-2-one
Traditional Namepalonosetron
SMILES[H][C@@]12CCCC3=C1C(=CC=C3)C(=O)N(C2)[C@@H]1CN2CCC1CC2
InChI IdentifierInChI=1S/C19H24N2O/c22-19-16-6-2-4-14-3-1-5-15(18(14)16)11-21(19)17-12-20-9-7-13(17)8-10-20/h2,4,6,13,15,17H,1,3,5,7-12H2/t15-,17+/m0/s1
InChI KeyCPZBLNMUGSZIPR-DOTOQJQBSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as isoquinolones and derivatives. These are aromatic polycyclic compounds containing a ketone bearing isoquinoline moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIsoquinolines and derivatives
Sub ClassIsoquinolones and derivatives
Direct ParentIsoquinolones and derivatives
Alternative Parents
Substituents
  • Isoquinolone
  • Tetrahydroisoquinoline
  • Tetralin
  • Quinuclidine
  • Piperidine
  • Benzenoid
  • Tertiary carboxylic acid amide
  • Amino acid or derivatives
  • Tertiary aliphatic amine
  • Carboxamide group
  • Lactam
  • Tertiary amine
  • Azacycle
  • Carboxylic acid derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Amine
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.46 g/LALOGPS
logP2.72ALOGPS
logP2.55ChemAxon
logS-2.8ALOGPS
pKa (Strongest Basic)7.97ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area23.55 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity88.52 m³·mol⁻¹ChemAxon
Polarizability33.87 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a59-1930000000-313ee8b58bac090cf92bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0390000000-1f369979b1f72a5ee284Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-fb9aedbacdd6c36fc28fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-1900000000-c3e8de8e1e3144a09111Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-863b9de7abaa4a8faed6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0290000000-bc7a738473feda7daae8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bwi-0920000000-8186e5fa7f2e00ab5822Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-7a52ccd6b13581152274Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ot-0890000000-255810544f96c817dc6bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dj-0910000000-12f66bfb13295bb786d3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-6097eef1edfc41faed9bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0090000000-6097eef1edfc41faed9bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0930000000-066882119f6fe95ff3f5Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0014521
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPalonosetron
Chemspider ID130656
ChEBI ID812387
PubChem Compound ID148211
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Stoltz R, Parisi S, Shah A, Macciocchi A: Pharmacokinetics, metabolism and excretion of intravenous [l4C]-palonosetron in healthy human volunteers. Biopharm Drug Dispos. 2004 Nov;25(8):329-37.
2. Stoltz R, Cyong JC, Shah A, Parisi S: Pharmacokinetic and safety evaluation of palonosetron, a 5-hydroxytryptamine-3 receptor antagonist, in U.S. and Japanese healthy subjects. J Clin Pharmacol. 2004 May;44(5):520-31.
3. Rubenstein EB: Palonosetron: a unique 5-HT3 receptor antagonist indicated for the prevention of acute and delayed chemotherapy-induced nausea and vomiting. Clin Adv Hematol Oncol. 2004 May;2(5):284-9.
4. De Leon A: Palonosetron (Aloxi): a second-generation 5-HT(3) receptor antagonist for chemotherapy-induced nausea and vomiting. Proc (Bayl Univ Med Cent). 2006 Oct;19(4):413-6.
5. Yang LP, Scott LJ: Palonosetron: in the prevention of nausea and vomiting. Drugs. 2009 Nov 12;69(16):2257-78. doi: 10.2165/11200980-000000000-00000.
6. Siddiqui MA, Scott LJ: Palonosetron. Drugs. 2004;64(10):1125-32; discussion 1133-4.
7. Eisenberg P, MacKintosh FR, Ritch P, Cornett PA, Macciocchi A: Efficacy, safety and pharmacokinetics of palonosetron in patients receiving highly emetogenic cisplatin-based chemotherapy: a dose-ranging clinical study. Ann Oncol. 2004 Feb;15(2):330-7.