Details
Stereochemistry | ACHIRAL |
Molecular Formula | C19H20N2O3 |
Molecular Weight | 324.3737 |
Optical Activity | NONE |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
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-
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.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1899 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9341357 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Preventing | ANZEMET Approved UseANZEMET 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 Date8.7393599E11 |
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Preventing | ANZEMET Approved UseANZEMET 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 Date8.7393599E11 |
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Palliative | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
320 ng/mL |
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 |
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 |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
7.3 h |
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 |
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 |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
27% |
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: Page: p.33 |
healthy, 19 - 45 n = 24 Health Status: healthy Age Group: 19 - 45 Sex: M Population Size: 24 Sources: Page: p.33 |
Other AEs: Defect conduction intraventricular... Other AEs: Defect conduction intraventricular Sources: Page: p.33 |
200 mg single, oral Highest studied dose Dose: 200 mg Route: oral Route: single Dose: 200 mg Sources: Page: p.33 |
healthy, 19 - 45 n = 24 Health Status: healthy Age Group: 19 - 45 Sex: M Population Size: 24 Sources: Page: p.33 |
Other AEs: Defect conduction intraventricular... Other AEs: Defect conduction intraventricular Sources: Page: p.33 |
100 mg single, oral Recommended Dose: 100 mg Route: oral Route: single Dose: 100 mg Sources: Page: p.5 |
unhealthy Health Status: unhealthy Condition: Nausea and vomiting associated with cancer chemotherapy Sources: Page: p.5 |
Other AEs: QT interval prolonged, Torsade de pointes... Other AEs: QT interval prolonged Sources: Page: p.5Torsade de pointes PR interval prolonged QRS prolonged Atrioventricular block (grade 3-5) Cardiac arrest (grade 3-5) Arrhythmia ventricular (grade 3-5) |
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: Page: p.33 |
healthy, 19 - 45 n = 24 Health Status: healthy Age Group: 19 - 45 Sex: M Population Size: 24 Sources: Page: p.33 |
|
Defect conduction intraventricular | 200 mg single, oral Highest studied dose Dose: 200 mg Route: oral Route: single Dose: 200 mg Sources: Page: p.33 |
healthy, 19 - 45 n = 24 Health Status: healthy Age Group: 19 - 45 Sex: M Population Size: 24 Sources: Page: p.33 |
|
PR interval prolonged | 100 mg single, oral Recommended Dose: 100 mg Route: oral Route: single Dose: 100 mg Sources: Page: p.5 |
unhealthy Health Status: unhealthy Condition: Nausea and vomiting associated with cancer chemotherapy Sources: Page: p.5 |
|
QRS prolonged | 100 mg single, oral Recommended Dose: 100 mg Route: oral Route: single Dose: 100 mg Sources: Page: p.5 |
unhealthy Health Status: unhealthy Condition: Nausea and vomiting associated with cancer chemotherapy Sources: Page: p.5 |
|
QT interval prolonged | 100 mg single, oral Recommended Dose: 100 mg Route: oral Route: single Dose: 100 mg Sources: Page: p.5 |
unhealthy Health Status: unhealthy Condition: Nausea and vomiting associated with cancer chemotherapy Sources: Page: p.5 |
|
Torsade de pointes | 100 mg single, oral Recommended Dose: 100 mg Route: oral Route: single Dose: 100 mg Sources: Page: p.5 |
unhealthy Health Status: unhealthy Condition: Nausea and vomiting associated with cancer chemotherapy Sources: Page: p.5 |
|
Arrhythmia ventricular | grade 3-5 | 100 mg single, oral Recommended Dose: 100 mg Route: oral Route: single Dose: 100 mg Sources: Page: p.5 |
unhealthy Health Status: unhealthy Condition: Nausea and vomiting associated with cancer chemotherapy Sources: Page: p.5 |
Atrioventricular block | grade 3-5 | 100 mg single, oral Recommended Dose: 100 mg Route: oral Route: single Dose: 100 mg Sources: Page: p.5 |
unhealthy Health Status: unhealthy Condition: Nausea and vomiting associated with cancer chemotherapy Sources: Page: p.5 |
Cardiac arrest | grade 3-5 | 100 mg single, oral Recommended Dose: 100 mg Route: oral Route: single Dose: 100 mg Sources: Page: p.5 |
unhealthy Health Status: unhealthy Condition: Nausea and vomiting associated with cancer chemotherapy Sources: Page: p.5 |
PubMed
Title | Date | PubMed |
---|---|---|
Randomized open-label trial of dolasetron for the control of nausea and vomiting associated with high-dose chemotherapy with hematopoietic stem cell transplantation. | 2001 |
|
Placebo-controlled comparison of dolasetron and metoclopramide in preventing postoperative nausea and vomiting in patients undergoing hysterectomy. | 2001 Apr |
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[Prophylaxis of nausea and vomiting after thyroid surgery: comparison of oral and intravenous dolasetron with intravenous droperidol and placebo]. | 2001 Jul |
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Efficacy of single-dose intravenous dolasetron versus ondansetron in the prevention of postoperative nausea and vomiting. | 2001 Jun |
|
Dolasetron for chemo nausea. | 2001 Mar |
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The effect of timing of dolasetron administration on its efficacy as a prophylactic antiemetic in the ambulatory setting. | 2001 Oct |
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Granisetron vs ondansetron: is it a question of duration of 5-HT3 receptor blockade? | 2002 May 20 |
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[Prevention of post-operative nausea and vomiting. Randomised comparison of dolasetron versus dolasetron plus dexamethasone]. | 2003 Feb |
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Patient outcomes after therapeutic interchange of dolasetron for granisetron. | 2003 May 15 |
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[Blocking nociceptive afferents by retrobulbar bupivacaine does not decrease nausea and vomiting after propofol-remifentanil anaesthesia]. | 2003 Nov |
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Randomized, double-blind trial of dolasetron versus droperidol for prophylaxis of postoperative nausea and vomiting in patients undergoing TRAM flap breast reconstruction surgery. | 2003 Nov |
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Stability of dolasetron in two oral liquid vehicles. | 2003 Nov 1 |
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Effects of imatinib mesylate (STI571, Glivec) on the pharmacokinetics of simvastatin, a cytochrome p450 3A4 substrate, in patients with chronic myeloid leukaemia. | 2003 Nov 17 |
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QT prolongation and fatal arrhythmias: a review of clinical implications and effects of drugs. | 2003 Nov-Dec |
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Comparison of oral dolasetron and ondansetron in the prophylaxis of postoperative nausea and vomiting in children. | 2003 Oct |
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Timing of administration of dolasetron affects dose necessary to prevent postoperative nausea and vomiting. | 2004 Aug |
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Selective serotonin 5-HT3 receptor antagonists for postoperative nausea and vomiting: are they all the same? | 2005 |
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Pharmacokinetics of palonosetron in combination with aprepitant in healthy volunteers. | 2005 Apr |
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Dolasetron versus ondansetron for the treatment of postoperative nausea and vomiting. | 2005 Feb |
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Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
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Prevention and treatment of postoperative nausea and vomiting. | 2005 Jun 15 |
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Prophylaxis of postoperative nausea and vomiting in patients scheduled for breast surgery. | 2006 |
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Drugs for preventing postoperative nausea and vomiting. | 2006 Jul 19 |
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Relative efficacy of ondansetron, granisetron, dolasetron and palonosetron in controlling acute nausea and vomiting associated with platinum-based chemotherapy. | 2006 Jun |
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Anesthesiologists' practice patterns for treatment of postoperative nausea and vomiting in the ambulatory Post Anesthesia Care Unit. | 2006 Jun 1 |
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New antiemetic drugs. | 2006 Mar |
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Meta-analysis of the use of rescue antiemetics following PONV prophylactic failure with 5-HT3 antagonist/dexamethasone versus single-agent therapies. | 2006 May |
|
Prophylaxis of postoperative vomiting in children undergoing tonsillectomy: a systematic review and meta-analysis. | 2006 Nov |
Patents
Sample Use Guides
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:
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N0000175817
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LIVERTOX |
321
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A04AA04
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NCI_THESAURUS |
C94726
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NDF-RT |
N0000175818
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WHO-VATC |
QA04AA04
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NCI_THESAURUS |
C267
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M4728
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139014-62-3
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CHEMBL2368925
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DTXSID4048276
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82WI2L7Q6E
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68091
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3931
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Dolasetron
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115956-12-2
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C060344
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SUB06352MIG
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C61735
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82WI2L7Q6E
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ACTIVE MOIETY
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