Palonosetron (CED0006010)

Record Information
Version1.0
Creation Date2016-05-25 18:20:04 UTC
Update Date2026-05-14 16:37:01 UTC
Accession NumberCHEM022102
Identification
Common NamePalonosetron
ClassSmall Molecule
Description
Palonosetron is an organic compound with the formula C19H24N2O and an average molecular weight of 296.41 g/mol. Palonosetron belongs to the isoquinolones and derivatives, a subclass of isoquinolines and derivatives within the organic compounds. It is categorized as an organoheterocyclic compound. The compound acts as an antagonist of the 5-hydroxytryptamine receptor 3A (HTR3A). It is found in or released from three recorded sources: healthcare, pharmaceuticals & veterinary products (specifically antiemetics and antinauseants), electrical & electronic equipment (line transmission systems), and household cleaning & consumer products (non electric simulated smoking devices). Recorded exposure routes for this substance include oral and intravenous administration.
Contaminant TypeNot Available
Chemical Structure
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
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0a59-1930000000-313ee8b58bac090cf92bNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0390000000-1f369979b1f72a5ee284Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0900000000-fb9aedbacdd6c36fc28fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-1900000000-c3e8de8e1e3144a09111Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0090000000-863b9de7abaa4a8faed6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0290000000-bc7a738473feda7daae8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0bwi-0920000000-8186e5fa7f2e00ab5822Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0090000000-7a52ccd6b13581152274Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01ot-0890000000-255810544f96c817dc6bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03dj-0910000000-12f66bfb13295bb786d3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0090000000-6097eef1edfc41faed9bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0090000000-6097eef1edfc41faed9bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0930000000-066882119f6fe95ff3f5Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
268.0Log mg/kg[150:480]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
249Antiemetics and antinauseantsHealthcare, pharmaceuticals & veterinary productsNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
651Purses Money Bags WalletsTextiles, leather & furnishingsNot Available
Pathways
3 pathways
Palonosetron Serotonin antagonist Action Pathway
Palonosetron Serotonin antagonist Action Pathway
Palonosetron Drug Metabolism Action Pathway
Palonosetron Drug Metabolism Action Pathway
Palonosetron Predicted Metabolism Pathway
Palonosetron Predicted Metabolism Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structure5-hydroxytryptamine receptor 3BO95264HumansPredicted (SEA)0.0778492
5-hydroxytryptamine receptor 3A structureClick to view 3D structure5-hydroxytryptamine receptor 3AP46098HumansPredicted (SEA)4.04816
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansPredicted (SEA)218.289
Click to view 3D structureMuscarinic acetylcholine receptor M2P10980Rattus norvegicusPredicted (SEA)45.931
Cytochrome P450 1A2 structureClick to view 3D structureCytochrome P450 1A2P05177HumansPredicted (SEA)1030.26
Click to view 3D structureMuscarinic acetylcholine receptor M1P08482Rattus norvegicusPredicted (SEA)102.605
Click to view 3D structureMuscarinic acetylcholine receptor M1Q8WMX0Bos taurusPredicted (SEA)11.1324
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansPredicted (SEA)1789.44
Muscarinic acetylcholine receptor M1 structureClick to view 3D structureMuscarinic acetylcholine receptor M1P11229HumansPredicted (SEA)513.26
Muscarinic acetylcholine receptor M2 structureClick to view 3D structureMuscarinic acetylcholine receptor M2P08172HumansPredicted (SEA)481.731
D(2) dopamine receptor structureClick to view 3D structureD(2) dopamine receptorP14416HumansPredicted (SEA)1484.27
Click to view 3D structure5-hydroxytryptamine receptor 1AP19327Rattus norvegicusPredicted (SEA)917.22
Muscarinic acetylcholine receptor M3 structureClick to view 3D structureMuscarinic acetylcholine receptor M3P20309HumansPredicted (SEA)539.262
Click to view 3D structure5-hydroxytryptamine receptor 7P32305Rattus norvegicusPredicted (SEA)286.485
5-hydroxytryptamine receptor 1A structureClick to view 3D structure5-hydroxytryptamine receptor 1AP08908HumansPredicted (SEA)1508.41
Neuronal acetylcholine receptor subunit alpha-7 structureClick to view 3D structureNeuronal acetylcholine receptor subunit alpha-7P36544HumansPredicted (SEA)185.982
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)3569.62
Click to view 3D structureD(1A) dopamine receptorP18901Rattus norvegicusPredicted (SEA)471.922
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)3323.93
Click to view 3D structureMuscarinic acetylcholine receptor M3P08483Rattus norvegicusPredicted (SEA)65.8604
Click to view 3D structureNeuronal acetylcholine receptor subunit alpha-7Q05941Rattus norvegicusPredicted (SEA)77.8492
Protein cereblon structureClick to view 3D structureProtein cereblonQ96SW2HumansPredicted (SEA)16.0369
Cytochrome P450 2C19 structureClick to view 3D structureCytochrome P450 2C19P33261HumansPredicted (SEA)2578.21
5-hydroxytryptamine receptor 7 structureClick to view 3D structure5-hydroxytryptamine receptor 7P34969HumansPredicted (SEA)1348.5
5-hydroxytryptamine receptor 2A structureClick to view 3D structure5-hydroxytryptamine receptor 2AP28223HumansPredicted (SEA)2179.54
Concentrations
Not Available
External Links
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.