DOLASETRON

US Previously Marketed

Details

Stereochemistry	ACHIRAL
Molecular Formula	C19H20N2O3
Molecular Weight	324.3744
Optical Activity	NONE
Defined Stereocenters	4 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12C[C@H](C[C@H]3C[C@@H](C1)C(=O)CN23)OC(=O)C4=CNC5=C4C=CC=C5

InChI

InChIKey=UKTAZPQNNNJVKR-YXSUXZIUSA-N

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-

HIDE SMILES / InChI

Molecular Formula	C19H20N2O3
Molecular Weight	324.3744
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/020623s008lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/21036635

Dolasetron is an antinauseant and antiemetic agent, which is approved as a mesylate salt under the brand name anzement for the prevention of nausea and vomiting associated with moderately emetogenic cancer chemotherapy, including initial and repeat courses; and for the prevention of postoperative nausea and vomiting. Dolasetron is a highly specific and selective serotonin 5-HT3 receptor antagonist. The serotonin 5-HT3 receptors are located on the nerve terminals of the vagus in the periphery and centrally in the chemoreceptor trigger zone of the area postrema. It is thought that chemotherapeutic agents produce nausea and vomiting by releasing serotonin from the enterochromaffin cells of the small intestine, and that the released serotonin then activates 5-HT3 receptors located on vagal efferents to initiate the vomiting reflex. This drug is not shown to have activity at other known serotonin receptors, and has low affinity for dopamine receptors. Dolasetron mesilate is rapidly reduced by carbonyl reductase to form its major pharmacologically active metabolite reduced dolasetron. In addition dolasetron was in the phase III clinical trials for the investigation, that intravenous using of dolasetron mesilate reduces pain intensity in patients with fibromyalgia.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serotonin 3a (5-HT3a) receptor 48 Target ID: CHEMBL1899 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9341357	Antagonist 2849

Conditions

Condition	Modality	Highest Phase	Product
Postoperative nausea and vomiting 31 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/020623s008lbl.pdf	Preventing	Approved 8583	ANZEMET Approved Use ANZEMET Tablets are indicated for the prevention of nausea and vomiting associated with moderately emetogenic cancer chemotherapy, including initial and repeat courses in adults and children 2 years and older. Launch Date 1997
Nausea and vomiting associated with moderately emetogenic cancer chemotherapy 4 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/020623s008lbl.pdf	Preventing	Approved 8583	ANZEMET Approved Use ANZEMET Tablets are indicated for the prevention of nausea and vomiting associated with moderately emetogenic cancer chemotherapy, including initial and repeat courses in adults and children 2 years and older. Launch Date 1997
Fibromyalgia 90 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21036635	Palliative	Phase III 665	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
320 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020623s010lbl.pdf%2C020624s023lbl.pdf	100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered:		HYDRODOLASETRON plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
556 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020623s010lbl.pdf%2C020624s023lbl.pdf	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:		HYDRODOLASETRON plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
7.3 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020623s010lbl.pdf%2C020624s023lbl.pdf	100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered:		HYDRODOLASETRON plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
8.1 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020623s010lbl.pdf%2C020624s023lbl.pdf	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:		HYDRODOLASETRON plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
27% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020623s010lbl.pdf%2C020624s023lbl.pdf	100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered:		HYDRODOLASETRON plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
200 mg single, intravenous Highest studied dose Dose: 200 mg Route: intravenous Route: single Dose: 200 mg Sources: https://pubmed.ncbi.nlm.nih.gov/10086835	healthy, 19 - 45 Health Status: healthy Age Group: 19 - 45 Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/10086835	Other AEs: Defect conduction intraventricular... Other AEs: Defect conduction intraventricular Sources: https://pubmed.ncbi.nlm.nih.gov/10086835
200 mg single, oral Highest studied dose Dose: 200 mg Route: oral Route: single Dose: 200 mg Sources: https://pubmed.ncbi.nlm.nih.gov/10086835	healthy, 19 - 45 Health Status: healthy Age Group: 19 - 45 Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/10086835	Other AEs: Defect conduction intraventricular... Other AEs: Defect conduction intraventricular Sources: https://pubmed.ncbi.nlm.nih.gov/10086835
100 mg single, oral Recommended Dose: 100 mg Route: oral Route: single Dose: 100 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020623s010lbl.pdf%2C020624s023lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020623s010lbl.pdf%2C020624s023lbl.pdf	Other AEs: QT interval prolonged, Torsade de pointes... Other AEs: QT interval prolonged Torsade de pointes PR interval prolonged QRS prolonged Atrioventricular block (grade 3-5) Cardiac arrest (grade 3-5) Arrhythmia ventricular (grade 3-5) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020623s010lbl.pdf%2C020624s023lbl.pdf

AEs

AE	Significance	Dose	Population
Defect conduction intraventricular		200 mg single, intravenous Highest studied dose Dose: 200 mg Route: intravenous Route: single Dose: 200 mg Sources: https://pubmed.ncbi.nlm.nih.gov/10086835	healthy, 19 - 45 Health Status: healthy Age Group: 19 - 45 Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/10086835
Defect conduction intraventricular		200 mg single, oral Highest studied dose Dose: 200 mg Route: oral Route: single Dose: 200 mg Sources: https://pubmed.ncbi.nlm.nih.gov/10086835	healthy, 19 - 45 Health Status: healthy Age Group: 19 - 45 Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/10086835
PR interval prolonged		100 mg single, oral Recommended Dose: 100 mg Route: oral Route: single Dose: 100 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020623s010lbl.pdf%2C020624s023lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020623s010lbl.pdf%2C020624s023lbl.pdf
QRS prolonged		100 mg single, oral Recommended Dose: 100 mg Route: oral Route: single Dose: 100 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020623s010lbl.pdf%2C020624s023lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020623s010lbl.pdf%2C020624s023lbl.pdf
QT interval prolonged		100 mg single, oral Recommended Dose: 100 mg Route: oral Route: single Dose: 100 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020623s010lbl.pdf%2C020624s023lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020623s010lbl.pdf%2C020624s023lbl.pdf
Torsade de pointes		100 mg single, oral Recommended Dose: 100 mg Route: oral Route: single Dose: 100 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020623s010lbl.pdf%2C020624s023lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020623s010lbl.pdf%2C020624s023lbl.pdf
Arrhythmia ventricular	grade 3-5	100 mg single, oral Recommended Dose: 100 mg Route: oral Route: single Dose: 100 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020623s010lbl.pdf%2C020624s023lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020623s010lbl.pdf%2C020624s023lbl.pdf
Atrioventricular block	grade 3-5	100 mg single, oral Recommended Dose: 100 mg Route: oral Route: single Dose: 100 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020623s010lbl.pdf%2C020624s023lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020623s010lbl.pdf%2C020624s023lbl.pdf
Cardiac arrest	grade 3-5	100 mg single, oral Recommended Dose: 100 mg Route: oral Route: single Dose: 100 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020623s010lbl.pdf%2C020624s023lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020623s010lbl.pdf%2C020624s023lbl.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946		substrate 1388	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP3A 220 UGT 219 FMO 34

Drug as victim

Target	Modality	Activity
CYP2D6 1388	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020623s012lbl.pdf#page=2 Page: 2.0	yes
CYP3A 220	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020623s012lbl.pdf#page=2 Page: 2.0	yes
CYP3A4 1946	substrate 4014 Sources: https://dmd.aspetjournals.org/content/24/5/602.short	yes
FMO 34	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16192915/	yes
UGT 219	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020623s012lbl.pdf#page=2 Page: 2.0	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubmed.ncbi.nlm.nih.gov/11046096/

Sourcing

Vendor/Aggregator	ID	URL
AstaTech	C71510
BOC Sciences	115956-12-2
eMolecules	195187818
mcule	MCULE-2311889447
MolPort	MolPort-046-851-633
PI Chemicals	PI-21727
Sigma Aldrich	CDS021594
Vesino Industrial Co Ltd	VA10755
ZINC	ZINC000000897298	http://zinc15.docking.org/substances/ZINC000000897298

PubMed

Title	Date	PubMed
A meta-analysis comparing the efficacy of four 5-HT3-receptor antagonists for acute chemotherapy-induced emesis.	2007-09	17205281
[Prevention and treatment of postoperative nausea and vomiting in children. An evidence-based approach].	2007-06	17521856
Management of radiation-induced nausea and vomiting.	2007-04	17379085
Randomized comparison of two anti-emetic strategies in high-risk patients undergoing day-case gynaecological surgery.	2007-04	17317757
Systemic anticancer therapy in gynecological cancer patients with renal dysfunction.	2007-02-21	17309673
Tremor in multiple sclerosis.	2007-02	17318714
[Dolasetron and shivering. A prospective randomized placebo-controlled pharmaco-economic evaluation].	2007-01	17021884
Acute gastroenteritis in children: role of anti-emetic medication for gastroenteritis-related vomiting.	2007	17523698
Management of postoperative nausea and vomiting in children.	2007	17291136
Systematic review on the recurrence of postoperative nausea and vomiting after a first episode in the recovery room - implications for the treatment of PONV and related clinical trials.	2006-12-13	17166262
Pharmacological prophylaxis and management of adult postoperative/postdischarge nausea and vomiting.	2006-12	17169748
Prophylaxis of postoperative vomiting in children undergoing tonsillectomy: a systematic review and meta-analysis.	2006-11	17005507
Inspired oxygen fraction of 0.8 compared with 0.4 does not further reduce postoperative nausea and vomiting in dolasetron-treated patients undergoing laparoscopic cholecystectomy.	2006-11	16963789
New approaches to chemotherapy-induced nausea and vomiting: from neuropharmacology to clinical investigations.	2006-10-13	17034670
Palonosetron: a second-generation 5-hydroxytryptamine receptor antagonist.	2006-10	17026451
Dolasetron versus ondansetron as single-agent prophylaxis for patients at increased risk for postoperative nausea and vomiting: a prospective, double-blind, randomized trial.	2006-09	17036618
Drugs for preventing postoperative nausea and vomiting.	2006-07-19	16856030
Lack of effect of aprepitant on hydrodolasetron pharmacokinetics in CYP2D6 extensive and poor metabolizers.	2006-07	16809805
Anesthesiologists' practice patterns for treatment of postoperative nausea and vomiting in the ambulatory Post Anesthesia Care Unit.	2006-06-01	16740165
Relative efficacy of ondansetron, granisetron, dolasetron and palonosetron in controlling acute nausea and vomiting associated with platinum-based chemotherapy.	2006-06	16984743
Laparoscopic cholecystectomy and management of biliary tract stones in a freestanding ambulatory surgery center.	2006-05-20	16709357
Meta-analysis of the use of rescue antiemetics following PONV prophylactic failure with 5-HT3 antagonist/dexamethasone versus single-agent therapies.	2006-05	16670361
Meta-analysis of the safety of 5-HT3 antagonists with dexamethasone or droperidol for prevention of PONV.	2006-05	16670360
Prevention of postoperative nausea and vomiting with granisetron and dolasetron in relation to CYP2D6 genotype.	2006-04	16551910
Paravertebral blocks provide superior same-day recovery over general anesthesia for patients undergoing inguinal hernia repair.	2006-04	16551902
New antiemetic drugs.	2006-03	16608997
Purification and characterization of akr1b10 from human liver: role in carbonyl reduction of xenobiotics.	2006-03	16381663
The role of 5-HT3 receptor antagonists in preventing postoperative nausea and vomiting.	2006-01	16528908
Measuring the maintenance of daily life activities using the functional living index-emesis (FLIE) in patients receiving moderately emetogenic chemotherapy.	2006-01	16444851
Prophylaxis of postoperative nausea and vomiting in patients scheduled for breast surgery.	2006	17163275
The Breast Journal regrettably is retracting a manuscript entitled, " Dolasetron decreases postoperative nausea and vomiting after breast surgery".	2005-12-21	16363099
Treatment of postoperative nausea and vomiting with dolasetron versus ondansetron: is there a conflict of interest?	2005-12	16301287
Prophylactic intravenous ondansetron and dolasetron in intrathecal morphine-induced pruritus: a randomized, double-blinded, placebo-controlled study.	2005-11	16244023
Employment of substandard antiemetic prophylaxis in recent trials of chemotherapy-induced nausea and vomiting.	2005-11	16204394
Cytochrome P450 2D6 metabolism and 5-hydroxytryptamine type 3 receptor antagonists for postoperative nausea and vomiting.	2005-10	16192915
Antiemetics of the 5-hydroxytryptamine 3A antagonist class inhibit muscle nicotinic acetylcholine receptors.	2005-09	16115980
Dolasetron and peri-operative cardiac arrhythmia.	2005-09	16115265
5-hydroxytryptamine type-3 receptor antagonists for chemotherapy-induced and radiotherapy-induced nausea and emesis: can we safely reduce the dose of administered agents?	2005-07-01	15929119
Prevention and treatment of postoperative nausea and vomiting.	2005-06-15	15947124
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005-06	15962942
Pharmacokinetics of palonosetron in combination with aprepitant in healthy volunteers.	2005-04	15899109
Docetaxel (Taxotere), cisplatin, UFT, and leucovorin combination chemotherapy in advanced gastric cancer.	2005-03-14	15726097
Coronary vasospasm leading to an acute myocardial infarction after the administration of dolasetron.	2005-02	15721735
Dolasetron versus ondansetron for the treatment of postoperative nausea and vomiting.	2005-02	15673860
Acute emesis: moderately emetogenic chemotherapy.	2005-02	15565276
The utility of antiemetics in the prevention and treatment of postoperative nausea and vomiting in patients scheduled for laparoscopic cholecystectomy.	2005	16178752
Selective serotonin 5-HT3 receptor antagonists for postoperative nausea and vomiting: are they all the same?	2005	15740177
Carbonyl reduction of naltrexone and dolasetron by oxidoreductases isolated from human liver cytosol.	2004-12	15563768
Palonosetron: a unique 5-HT3 receptor antagonist indicated for the prevention of acute and delayed chemotherapy-induced nausea and vomiting.	2004-05	16163194
Spectrum of use and tolerability of 5-HT3 receptor antagonists.	2004	15515406

Patents

Sample Use Guides

In Vivo Use Guide

Prevention of Cancer Chemotherapy-Induced Nausea and Vomiting. Adults: the recommended oral dosage of ANZEMET (dolasetron mesylate) is 100 mg given within one hour before chemotherapy. Pediatric Patients: the recommended oral dosage in pediatric patients 2 to 16 years of age is 1.8 mg/kg given within one hour before chemotherapy, up to a maximum of 100 mg. Prevention of Postoperative Nausea and Vomiting. Adults: the recommended oral dosage of ANZEMET (dolasetron mesylate) is 100 mg within two hours before surgery. Pediatric Patients: the recommended oral dosage in pediatric patients 2 to 16 years of age is 1.2 mg/kg given within two hours before surgery, up to a maximum of 100 mg. Safety and effectiveness in pediatric patients under 2 years of age have not been established. fibromyalgia: dolasetron (n = 29) 12.5mg/d via the intravenous route on 4 days at baseline (M0), 1 month (M1), 2 months (M2) and 3 months (M3) with follow-up to month 12.

Route of Administration: Other

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:06:37 GMT 2025` Edited by `admin` on `Mon Mar 31 18:06:37 GMT 2025`
Record UNII	82WI2L7Q6E
Record Status	`FAILED`
Record Version

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Name

Type

Language

DOLASETRON

Official Name

English

1H-INDOLE-3-CARBOXYLIC ACID, OCTAHYDRO-3-OXO-2,6-METHANO-2H-QUINOLIZIN-8-YL ESTER, (2.ALPHA.,6.ALPHA.,8.ALPHA.,9A.BETA.)-

Preferred Name

English

dolasetron [INN]

Common Name

English

INDOLE-3-CARBOXYLIC ACID, ESTER WITH (8R)-HEXAHYDRO-8-HYDROXY-2,6-METHANO-2H-QUINOLIZIN-3(4H)-ONE

Common Name

English

Dolasetron [WHO-DD]

Common Name

English

DOLASETRON [MI]

Common Name

English

DOLASETRON [VANDF]

Common Name

English

DOLASETRON [HSDB]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000175817