Dolasetron (CED0008846)

Record Information

Version

1.0

Creation Date

2016-05-25 18:22:46 UTC

Update Date

2026-08-20 02:53:13 UTC

Accession Number

CHEM022177

Identification

Common Name

Dolasetron

Class

Small Molecule

Description

Dolasetron is an organic compound with the chemical formula C19H20N2O3 and an average molecular weight of 324.37 g/mol. Dolasetron belongs to the indolecarboxylic acids and derivatives, a subclass of indoles and derivatives within the organic compounds. It is categorized under the superclass of organoheterocyclic compounds. In terms of biological activity, dolasetron acts as an antagonist of the 5-hydroxytryptamine receptor 3A (HTR3A). It is utilized in healthcare, pharmaceuticals, and veterinary products as an antiemetic and antinauseant. Recorded routes of exposure for the compound include oral and intravenous administration. The compound has been identified in seven recorded sources. These include household cleaning and consumer products such as tobacco smoke filters, cigar cigarettes, and other smoking requisites. It is also found in electrical and electronic equipment, specifically within antennas, line transmission systems, and electrically stimulated smoking devices.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Anzemet	HMDB
MDL 73147Ef	HMDB
MDL-73147Ef	HMDB
MDL 73,147Ef	HMDB
Octahydro-3-oxo-2,6-methano-2H-quinolizin-8-yl 1H-indole-3-carboxylate	HMDB
Dolasetron mesylate	HMDB
1H-Indole-3-carboxylic acid-trans-octahydro-3-oxo-2,6-methano-2H-quinolizin-8-yl ester methanesulfonate	HMDB
Dolasetron mesilate monohydrate	MeSH
1H-Indole-3-carboxylic acid, (6R,9as)-octahydro-3-oxo-2,6-methano-2H-quinolizin-8-yl ester, rel-, methanesulfonate, hydrate (1:1:1)	MeSH
Dolasetron mesylate monohydrate	MeSH
Indole-3-carboxylic acid, ester with (8R)-hexahydro-8-hydroxy-2,6-methano-2H-quinolizin-3(4H)-one	MeSH
(3R)-10-oxo-8-Azatricyclo[5.3.1.0³,⁸]undecan-5-yl 1H-indole-3-carboxylic acid	Generator
Dolasetron	MeSH
(3R)-10-oxo-8-Azatricyclo[5.3.1.0,]undecan-5-yl 1H-indole-3-carboxylic acid	Generator

Chemical Formula

C₁₉H₂₀N₂O₃

Average Molecular Mass

324.374 g/mol

Monoisotopic Mass

324.147 g/mol

CAS Registry Number

115956-12-2

IUPAC Name

(3R)-10-oxo-8-azatricyclo[5.3.1.0³,⁸]undecan-5-yl 1H-indole-3-carboxylate

Traditional Name

dolasetron

SMILES

[H][C@]12CC(CC3CC(C1)C(=O)CN23)OC(=O)C1=CNC2=CC=CC=C12

InChI Identifier

InChI=1S/C19H20N2O3/c22-18-10-21-12-5-11(18)6-13(21)8-14(7-12)24-19(23)16-9-20-17-4-2-1-3-15(16)17/h1-4,9,11-14,20H,5-8,10H2/t11?,12-,13?,14?/m1/s1

InChI Key

UKTAZPQNNNJVKR-DBBXXEFVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolecarboxylic acids and derivatives. Indolecarboxylic acids and derivatives are compounds containing a carboxylic acid group (or a derivative thereof) linked to an indole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolecarboxylic acids and derivatives

Direct Parent

Indolecarboxylic acids and derivatives

Alternative Parents

Substituents

Indolecarboxylic acid derivative
Quinolizidine
Indole
Quinuclidone
Pyrrole-3-carboxylic acid or derivatives
Quinuclidine
Piperidinone
Piperidine
Substituted pyrrole
Benzenoid
Vinylogous amide
Pyrrole
Heteroaromatic compound
Tertiary amine
Tertiary aliphatic amine
Carboxylic acid ester
Ketone
Amino acid or derivatives
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Azacycle
Amine
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.26 g/L	ALOGPS
logP	2.41	ALOGPS
logP	2.33	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	12.18	ChemAxon
pKa (Strongest Basic)	6.88	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	62.4 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	89.34 m³·mol⁻¹	ChemAxon
Polarizability	33.69 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-006x-1900000000-8dcd9035e77addcb92c2	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0809000000-e543237d634e768bf190	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03dl-0901000000-d6386713d3df49c9837e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00l6-0900000000-0b1c6b04e96536805498	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0509000000-085a8f6a1ddf99d931fe	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01b9-0903000000-3363bde3d5011e6d4a88	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0900000000-49ee7a167d32200b182c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0009000000-9b54b47c162811e47733	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0409000000-dcf423a8abd27c382925	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014l-1900000000-b5bcc02270654ef46e8e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0009000000-ffc9bb102611a33bd213	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0809000000-00ad969880df21e26b60	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0902000000-f4b49f170c3bb0df26cd	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
669.0	Log mg/kg	[380:1200]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
10	Insecticides	Agriculture & land management	Not Available
249	Antiemetics and antinauseants	Healthcare, pharmaceuticals & veterinary products	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available
518	Electrically Stimulated Smoking Devices	Electrical & Electronic Equipment	Not Available
525	Line Transmission Systems	Electrical & Electronic Equipment	Not Available
556	Cigar Cigarettes	Household cleaning & consumer products	Not Available
560	Other Smoking Requisites	Household cleaning & consumer products	Not Available
569	Tobacco Smoke Filters	Household cleaning & consumer products	Not Available
580	Manufacture Preparation Of Tobacco Products	Industrial manufacturing & chemical processing	Not Available
605	Pest Repellants	Agriculture & land management	Not Available
611	Anti Perspirants Or Body Deoderants	Personal care & cosmetics	Not Available
632	Apparel	Textiles, leather & furnishings	Not Available
650	Purses Luggage Hand Bags	Textiles, leather & furnishings	Not Available
651	Purses Money Bags Wallets	Textiles, leather & furnishings	Not Available

Pathways

2 pathways

Dolasetron Serotonin antagonist Action Pathway

Dolasetron Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Neuronal acetylcholine receptor subunit alpha-7	P36544	Humans	Predicted (SEA)	2.33548
Click to view 3D structure	Neuronal acetylcholine receptor subunit alpha-7	Q05941	Rattus norvegicus	Predicted (SEA)	5.13805
Click to view 3D structure	Neuronal acetylcholine receptor subunit alpha-7	P49582	Mus musculus	Predicted (SEA)	0.0778492
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P08908	Humans	Predicted (SEA)	268.813
Click to view 3D structure	Muscarinic acetylcholine receptor M5	P08912	Humans	Predicted (SEA)	43.5956
Click to view 3D structure	5-hydroxytryptamine receptor 3A	P46098	Humans	Predicted (SEA)	66.1718
Click to view 3D structure	Sodium-dependent serotonin transporter	P31645	Humans	Predicted (SEA)	189.174
Click to view 3D structure	D(2) dopamine receptor	P61169	Rat	Predicted (SEA)	290.923
Click to view 3D structure	5-hydroxytryptamine receptor 4	Q13639	Humans	Predicted (SEA)	34.2537
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Predicted (SEA)	959.803
Click to view 3D structure	Cytochrome P450 2D6	P10635	Humans	Predicted (SEA)	865.294
Click to view 3D structure	5-hydroxytryptamine receptor 4	O70528	Cavia porcellus	Predicted (SEA)	65.0819
Click to view 3D structure	Cytochrome P450 1A2	P05177	Humans	Predicted (SEA)	663.275
Click to view 3D structure	Cytochrome P450 2C9	P11712	Humans	Predicted (SEA)	1214.6
Click to view 3D structure	5-hydroxytryptamine receptor 4	Q62758	Rattus norvegicus	Predicted (SEA)	38.9246
Click to view 3D structure	Muscarinic acetylcholine receptor M3	P08483	Rattus norvegicus	Predicted (SEA)	21.4864
Click to view 3D structure	5-hydroxytryptamine receptor 2C	P28335	Humans	Predicted (SEA)	823.178
Click to view 3D structure	Muscarinic acetylcholine receptor M2	P10980	Rattus norvegicus	Predicted (SEA)	56.3628
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	1031.11
Click to view 3D structure	5-hydroxytryptamine receptor 2B	P41595	Humans	Predicted (SEA)	761.832
Click to view 3D structure	Galactosylgalactosylxylosylprotein 3-beta-glucuronosyltransferase 3	O94766	Humans	Predicted (SEA)	2.49118
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P19327	Rattus norvegicus	Predicted (SEA)	729.603
Click to view 3D structure	Sodium-dependent dopamine transporter	P23977	Rattus norvegicus	Predicted (SEA)	270.837
Click to view 3D structure	Alpha-1D adrenergic receptor	P25100	Humans	Predicted (SEA)	361.298
Click to view 3D structure	Cytochrome P450 2C19	P33261	Humans	Predicted (SEA)	1284.82