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Details

Stereochemistry ACHIRAL
Molecular Formula C19H20N2O3.CH4O3S.H2O
Molecular Weight 438.495
Optical Activity NONE
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DOLASETRON MESYLATE

SMILES

O.CS(O)(=O)=O.O=C(O[C@H]1C[C@@H]2C[C@@H]3C[C@@H](C1)N2CC3=O)C4=CNC5=C4C=CC=C5

InChI

InChIKey=QTFFGPOXNNGTGZ-LIFGOUTFSA-N
InChI=1S/C19H20N2O3.CH4O3S.H2O/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;1-5(2,3)4;/h1-4,9,11-14,20H,5-8,10H2;1H3,(H,2,3,4);1H2/t11-,12-,13+,14+;;

HIDE SMILES / InChI

Molecular Formula C19H20N2O3
Molecular Weight 324.3737
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula CH4O3S
Molecular Weight 96.106
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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 TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
ANZEMET
Preventing
ANZEMET
Palliative
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
320 ng/mL
100 mg single, intravenous
HYDRODOLASETRON plasma
Homo sapiens
556 ng/mL
200 mg single, oral
HYDRODOLASETRON plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
7.3 h
100 mg single, intravenous
HYDRODOLASETRON plasma
Homo sapiens
8.1 h
200 mg single, oral
HYDRODOLASETRON plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
27%
100 mg single, intravenous
HYDRODOLASETRON plasma
Homo sapiens

Doses

AEs

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as victim

Tox targets

Sourcing

PubMed

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
Record UNII
U3C8E5BWKR
Record Status Validated (UNII)
Record Version