SynCED: Ondansetron

Record Information

Version

1.0

Creation Date

2009-07-21 20:27:55 UTC

Update Date

2026-05-14 16:52:24 UTC

Accession Number

CHEM002297

Identification

Common Name

Ondansetron

Class

Small Molecule

Description

Ondansetron 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.

Contaminant Sources

FooDB Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amide
Amine
Anti-Anxiety Agent
Antiemetic
Antipruritic
Antipsychotic Agent
Drug
Ester
Food Toxin
Metabolite
Organic Compound
Serotonin Antagonist
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Zofran odt	Kegg
Zofran	HMDB
Zophren	HMDB
Zudan	HMDB
Monohydrochloride, ondansetron	HMDB
Monohydrochloride dihydrate, ondansetron	HMDB
Ondansetron monohydrochloride dihydrate	HMDB
Ondansetron, (R)-isomer	HMDB
Ondansetron hydrochloride	HMDB
Ondansetron monohydrochloride	HMDB
Ondansetron, (+,-)-isomer	HMDB
Dihydrate, ondansetron monohydrochloride	HMDB
Hydrochloride, ondansetron	HMDB
Ondansetron, (S)-isomer	HMDB

Chemical Formula

C₁₈H₁₉N₃O

Average Molecular Mass

293.363 g/mol

Monoisotopic Mass

293.153 g/mol

CAS Registry Number

99614-02-5

IUPAC Name

9-methyl-3-[(2-methyl-1H-imidazol-1-yl)methyl]-2,3,4,9-tetrahydro-1H-carbazol-4-one

Traditional Name

ondansetron

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 Key

FELGMEQIXOGIFQ-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Carbazoles

Direct Parent

Carbazoles

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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

carbazoles (CHEBI:7773 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Liver

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	231 - 232°C
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.25 g/L	ALOGPS
logP	2.56	ALOGPS
logP	2.35	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	15.39	ChemAxon
pKa (Strongest Basic)	7.34	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	39.82 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	86.78 m³·mol⁻¹	ChemAxon
Polarizability	33.16 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Toxicity Profile

Route of Exposure

Ondansetron is well absorbed after oral administration and undergoes limited first-pass metabolism.

Mechanism of Toxicity

Ondansetron is a selective serotonin 5-HT₃ receptor antagonist. The antiemetic activity of the drug is brought about through the inhibition of 5-HT₃ receptors present both centrally (medullary chemoreceptor zone) and peripherally (GI tract). This inhibition of 5-HT₃ receptors in turn inhibits the visceral afferent stimulation of the vomiting center, likely indirectly at the level of the area postrema, as well as through direct inhibition of serotonin activity within the area postrema and the chemoreceptor trigger zone.

Metabolism

Hepatic Half Life: 5.7 hours

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For the prevention of nausea and vomiting associated with emetogenic cancer chemotherapy, postoperation, and radiation. Also used for the treatment of postoperative nausea and vomiting.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Low blood pressure and fainting, sudden blindness, severe constipation

Treatment

There is no specific antidote for ondansetron overdose. Patients should be managed with appropriate supportive therapy. (8)

Concentrations

Not Available

External Links

DrugBank ID

DB00904

HMDB ID

HMDB0005035

FooDB ID

FDB023602

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

1646

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Peter Bod, Kalman Harsanyi, Ferenc Trischler, Eva Fekecs, Attila Csehi, Bela Hegedus, Eva Mersich nee Donat, Gyorgyi Szabo nee Komlosi, Erika Horvath nee Sziki, “Process for preparing ondansetron.” U.S. Patent US5478949, issued September, 1990.

MSDS

Link

General References

1. Mackinnon J W; Collin D T The chemistry of ondansetron. European journal of cancer & clinical oncology (1989), 25 Suppl 1 S61.

2. 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.

3. Graves T: Ondansetron: a new entity in emesis control. DICP. 1990 Nov;24(11 Suppl):S51-4.

Ondansetron (CHEM002297)

Structure for CHEM002297: Ondansetron