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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-10-17 10:18:12 UTC
Update Date2022-03-07 02:49:25 UTC
HMDB IDHMDB0005035
Secondary Accession Numbers
  • HMDB05035
Metabolite Identification
Common NameOndansetron
DescriptionOndansetron is a well tolerated drug with few side effects. Headache, constipation, and dizziness are the most commonly reported side effects associated with its use. There have been no significant drug interactions reported with this drugs use. It is broken down by the hepatic cytochrome P450 system and it has little effect on the metabolism of other drugs broken down by this system; Ondansetron is a serotonin 5-HT3 receptor antagonist used mainly to treat nausea and vomiting following chemotherapy. Its effects are thought to be on both peripheral and central nerves. One part is to reduce the activity of the vagus nerve, which is a nerve that activates the vomiting center in the medulla oblongata, the other is a blockage of serotonin receptors in the chemoreceptor trigger zone. It does not have much effect on vomiting due to motion sickness. This drug does not have any effect on dopamine receptors or muscarinic receptors; A competitive serotonin type 3 receptor antagonist. It is effective in the treatment of nausea and vomiting caused by cytotoxic chemotherapy drugs, including cisplatin, and has reported anxiolytic and neuroleptic properties; Ondansetron (INN) is a serotonin 5-HT3 receptor antagonist used mainly to treat nausea and vomiting following chemotherapy. Its effects are thought to be on both peripheral and central nerves. One part is to reduce the activity of the vagus nerve, which is a nerve that activates the vomiting center in the medulla oblongata, the other is a blockage of serotonin receptors in the chemoreceptor trigger zone. It does not have much effect on vomiting due to motion sickness. This drug does not have any effect on dopamine receptors or muscarinic receptors.
Structure
Data?1582752341
Synonyms
ValueSource
Zofran odtKegg
ZofranHMDB
ZophrenHMDB
ZudanHMDB
Monohydrochloride, ondansetronHMDB
Monohydrochloride dihydrate, ondansetronHMDB
Ondansetron monohydrochloride dihydrateHMDB
Ondansetron, (R)-isomerHMDB
Ondansetron hydrochlorideHMDB
Ondansetron monohydrochlorideHMDB
Ondansetron, (+,-)-isomerHMDB
Dihydrate, ondansetron monohydrochlorideHMDB
Hydrochloride, ondansetronHMDB
Ondansetron, (S)-isomerHMDB
Chemical FormulaC18H19N3O
Average Molecular Weight293.363
Monoisotopic Molecular Weight293.152812245
IUPAC Name9-methyl-3-[(2-methyl-1H-imidazol-1-yl)methyl]-2,3,4,9-tetrahydro-1H-carbazol-4-one
Traditional Nameondansetron
CAS Registry Number99614-02-5
SMILES
CN1C2=C(C3=CC=CC=C13)C(=O)C(CN1C=CN=C1C)CC2
InChI Identifier
InChI=1S/C18H19N3O/c1-12-19-9-10-21(12)11-13-7-8-16-17(18(13)22)14-5-3-4-6-15(14)20(16)2/h3-6,9-10,13H,7-8,11H2,1-2H3
InChI KeyFELGMEQIXOGIFQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassCarbazoles
Direct ParentCarbazoles
Alternative Parents
Substituents
  • Carbazole
  • N-alkylindole
  • Indole
  • Aryl ketone
  • Aryl alkyl ketone
  • N-methylpyrrole
  • N-substituted imidazole
  • Substituted pyrrole
  • Benzenoid
  • Imidazole
  • Pyrrole
  • Azole
  • Vinylogous amide
  • Heteroaromatic compound
  • Ketone
  • Azacycle
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point231 - 232 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM171.730932474
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.25 g/LALOGPS
logP2.56ALOGPS
logP2.35ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)15.39ChemAxon
pKa (Strongest Basic)7.34ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area39.82 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity86.78 m³·mol⁻¹ChemAxon
Polarizability33.16 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+167.59631661259
DarkChem[M-H]-168.30331661259
DeepCCS[M-2H]-198.95630932474
DeepCCS[M+Na]+174.52130932474
AllCCS[M+H]+170.332859911
AllCCS[M+H-H2O]+166.832859911
AllCCS[M+NH4]+173.632859911
AllCCS[M+Na]+174.532859911
AllCCS[M-H]-177.432859911
AllCCS[M+Na-2H]-176.932859911
AllCCS[M+HCOO]-176.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
OndansetronCN1C2=C(C3=CC=CC=C13)C(=O)C(CN1C=CN=C1C)CC24080.2Standard polar33892256
OndansetronCN1C2=C(C3=CC=CC=C13)C(=O)C(CN1C=CN=C1C)CC22849.1Standard non polar33892256
OndansetronCN1C2=C(C3=CC=CC=C13)C(=O)C(CN1C=CN=C1C)CC23037.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Ondansetron GC-MS (Non-derivatized) - 70eV, Positivesplash10-00nb-9840000000-3e06f3c6b7dfe3741b9d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ondansetron GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Ondansetron , positive-QTOFsplash10-0006-0590000000-1c293e5af06aedfb74e12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ondansetron LC-ESI-QFT , positive-QTOFsplash10-006x-0790000000-39dfc83ad8c54c21d83d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ondansetron 40V, Positive-QTOFsplash10-00e9-0900000000-9f75de47087ea727dbcc2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ondansetron 50V, Positive-QTOFsplash10-01b9-0900000000-908023356faf6f180af32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ondansetron 40V, Positive-QTOFsplash10-00e9-0900000000-5113a05488a50bd3517c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ondansetron 35V, Positive-QTOFsplash10-00ec-0950000000-99bd0224adfac797252e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ondansetron 10V, Positive-QTOFsplash10-0006-0090000000-b12ef22126884edee1272021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ondansetron 30V, Positive-QTOFsplash10-00e9-0910000000-bc8f444f5a685a24b58b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ondansetron 20V, Positive-QTOFsplash10-0006-0290000000-a83e2f6fa456e4784c8e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ondansetron 35V, Positive-QTOFsplash10-006x-0790000000-a881fb3942f2794a745a2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ondansetron 10V, Positive-QTOFsplash10-0006-0090000000-cd5ee2ea8a09e479ca822016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ondansetron 20V, Positive-QTOFsplash10-03dl-1190000000-b82994685853464410882016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ondansetron 40V, Positive-QTOFsplash10-001r-7930000000-39cdbd8680e338fc52d12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ondansetron 10V, Negative-QTOFsplash10-0006-3090000000-6ea6246fc080e90b47b92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ondansetron 20V, Negative-QTOFsplash10-001i-9040000000-063a9351d8828458eb6a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ondansetron 40V, Negative-QTOFsplash10-0006-9000000000-67ae58fff567a97b5c752016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ondansetron 10V, Positive-QTOFsplash10-0006-0090000000-1ddcbe24b3692363c9e92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ondansetron 20V, Positive-QTOFsplash10-0006-0090000000-92a569aa48de1bbd22ad2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ondansetron 40V, Positive-QTOFsplash10-06r6-1950000000-4c010488c047e61673852021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ondansetron 10V, Negative-QTOFsplash10-0006-0090000000-6e00cbfb66b0b752aed92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ondansetron 20V, Negative-QTOFsplash10-01ox-1090000000-975dfb36e43267beef532021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ondansetron 40V, Negative-QTOFsplash10-01vo-0290000000-9ef1b8637e2cdb4d9e6d2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue Locations
  • Liver
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00904
Phenol Explorer Compound IDNot Available
FooDB IDFDB023602
KNApSAcK IDNot Available
Chemspider ID4434
KEGG Compound IDC07325
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOndansetron
METLIN ID1646
PubChem Compound4595
PDB IDNot Available
ChEBI ID103183
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceMackinnon J W; Collin D T The chemistry of ondansetron. European journal of cancer & clinical oncology (1989), 25 Suppl 1 S61.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Tramer MR, Reynolds DJ, Moore RA, McQuay HJ: Efficacy, dose-response, and safety of ondansetron in prevention of postoperative nausea and vomiting: a quantitative systematic review of randomized placebo-controlled trials. Anesthesiology. 1997 Dec;87(6):1277-89. [PubMed:9416710 ]
  2. Graves T: Ondansetron: a new entity in emesis control. DICP. 1990 Nov;24(11 Suppl):S51-4. [PubMed:2148659 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that stimulate adenylate cyclase. It has a high affinity for tricyclic psychotropic drugs
Gene Name:
HTR6
Uniprot ID:
P50406
Molecular weight:
46953.6
General function:
Involved in extracellular ligand-gated ion channel activity
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor is a ligand-gated ion channel, which when activated causes fast, depolarizing responses in neurons. It is a cation-specific, but otherwise relatively nonselective, ion channel
Gene Name:
HTR3A
Uniprot ID:
P46098
Molecular weight:
55279.8
General function:
Involved in metal ion binding
Specific function:
Delivers copper to copper zinc superoxide dismutase (SOD1)
Gene Name:
CCS
Uniprot ID:
O14618
Molecular weight:
29040.4

Transporters

General function:
Involved in ATP binding
Specific function:
May supply copper to copper-requiring proteins within the secretory pathway, when localized in the trans-Golgi network. Under conditions of elevated extracellular copper, it relocalized to the plasma membrane where it functions in the efflux of copper from cells.
Gene Name:
ATP7A
Uniprot ID:
Q04656
Molecular weight:
163372.275