ContaminantDB: Dolasetron

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-25 18:22:46 UTC

Update Date

2016-11-09 01:17:26 UTC

Accession Number

CHEM022177

Identification

Common Name

Dolasetron

Class

Small Molecule

Description

Dolasetron is an antinauseant and antiemetic agent indicated for the prevention of nausea and vomiting associated with moderately-emetogenic cancer chemotherapy and for the prevention of postoperative nausea and vomiting. Dolasetron is a highly specific and selective serotonin 5-HT3 receptor antagonist. This drug has not shown to have activity at other known serotonin receptors, and has low affinity for dopamine receptors.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds

Contaminant Type

Not Available

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

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

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

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	1	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	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-1900000000-8dcd9035e77addcb92c2	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0809000000-e543237d634e768bf190	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dl-0901000000-d6386713d3df49c9837e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00l6-0900000000-0b1c6b04e96536805498	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0509000000-085a8f6a1ddf99d931fe	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01b9-0903000000-3363bde3d5011e6d4a88	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-0900000000-49ee7a167d32200b182c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0009000000-9b54b47c162811e47733	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0409000000-dcf423a8abd27c382925	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014l-1900000000-b5bcc02270654ef46e8e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0009000000-ffc9bb102611a33bd213	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0809000000-00ad969880df21e26b60	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-0902000000-f4b49f170c3bb0df26cd	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0014895

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Dolasetron

Chemspider ID

54666

ChEBI ID

Not Available

PubChem Compound ID

60654

Kegg Compound ID

C07866

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Balfour JA, Goa KL: Dolasetron. A review of its pharmacology and therapeutic potential in the management of nausea and vomiting induced by chemotherapy, radiotherapy or surgery. Drugs. 1997 Aug;54(2):273-98.

2. Gregory RE, Ettinger DS: 5-HT3 receptor antagonists for the prevention of chemotherapy-induced nausea and vomiting. A comparison of their pharmacology and clinical efficacy. Drugs. 1998 Feb;55(2):173-89.

3. Gan TJ: Selective serotonin 5-HT3 receptor antagonists for postoperative nausea and vomiting: are they all the same? CNS Drugs. 2005;19(3):225-38.

Dolasetron (CHEM022177)

Structure for CHEM022177: Dolasetron