Details
Stereochemistry | RACEMIC |
Molecular Formula | C18H19N3O |
Molecular Weight | 293.363 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1C2=C(C3=C1C=CC=C3)C(=O)C(CN4C=CN=C4C)CC2
InChI
InChIKey=FELGMEQIXOGIFQ-UHFFFAOYSA-N
InChI=1S/C18H19N3O/c1-12-19-9-10-21(12)11-13-7-8-16-17(18(13)22)14-5-3-4-6-15(14)20(16)2/h3-6,9-10,13H,7-8,11H2,1-2H3
Molecular Formula | C18H19N3O |
Molecular Weight | 293.363 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
DescriptionSources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020103s008s025,020605s008lbl.pdfCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/mesh/68017294 |
https://www.ncbi.nlm.nih.gov/pubmed/11474424
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020103s008s025,020605s008lbl.pdf
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/mesh/68017294 |
https://www.ncbi.nlm.nih.gov/pubmed/11474424
Ondansetron (ZOFRAN®) is a selective 5-HT3 receptor antagonist. It is effective in the treatment of nausea and vomiting caused by radiotherapy, anesthesia, surgery or cytotoxic chemotherapy drugs, including cisplatin, and has reported anxiolytic and neuroleptic properties. While its mechanism of action has not been fully characterized, ondansetron is not a dopamine-receptor antagonist. It is not certain whether ondansetron's antiemetic action is mediated centrally, peripherally, or in both sites. However, cytotoxic chemotherapy appears to be associated with release of serotonin from the enterochromaffin cells of the small intestine. The released serotonin may stimulate the vagal afferents through the 5-HT3 receptors and initiate the vomiting reflex.
CNS Activity
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9884318
Curator's Comment: Glaxo Wellcome is a predecessor of GlaxoSmithKline plc.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL1899 |
8.31 null [pKi] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Preventing | ZOFRAN Approved UsePrevention of nausea and vomiting associated with highly emetogenic cancer chemotherapy, including cisplatin ≥50 mg/m2. Prevention of nausea and vomiting associated with initial and repeat courses of moderately emetogenic cancer chemotherapy. Prevention of nausea and vomiting associated with radiotherapy in patients receiving either total body irradiation, single high-dose fraction to the abdomen, or daily fractions to the abdomen. Prevention of postoperative nausea and/or vomiting. As with other antiemetics, routine prophylaxis is not recommended for patients in whom there is little expectation that nausea and/or vomiting will occur postoperatively. In patients where nausea and/or vomiting must be avoided postoperatively, ZOFRAN® is recommended even where the incidence of postoperative nausea and/or vomiting is low. Launch Date1992 |
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Preventing | ZOFRAN Approved UsePrevention of nausea and vomiting associated with highly emetogenic cancer chemotherapy, including cisplatin ≥50 mg/m2. Prevention of nausea and vomiting associated with initial and repeat courses of moderately emetogenic cancer chemotherapy. Prevention of nausea and vomiting associated with radiotherapy in patients receiving either total body irradiation, single high-dose fraction to the abdomen, or daily fractions to the abdomen. Prevention of postoperative nausea and/or vomiting. As with other antiemetics, routine prophylaxis is not recommended for patients in whom there is little expectation that nausea and/or vomiting will occur postoperatively. In patients where nausea and/or vomiting must be avoided postoperatively, ZOFRAN® is recommended even where the incidence of postoperative nausea and/or vomiting is low. Launch Date1992 |
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Preventing | ZOFRAN Approved UsePrevention of nausea and vomiting associated with highly emetogenic cancer chemotherapy, including cisplatin ≥50 mg/m2. Prevention of nausea and vomiting associated with initial and repeat courses of moderately emetogenic cancer chemotherapy. Prevention of nausea and vomiting associated with radiotherapy in patients receiving either total body irradiation, single high-dose fraction to the abdomen, or daily fractions to the abdomen. Prevention of postoperative nausea and/or vomiting. As with other antiemetics, routine prophylaxis is not recommended for patients in whom there is little expectation that nausea and/or vomiting will occur postoperatively. In patients where nausea and/or vomiting must be avoided postoperatively, ZOFRAN® is recommended even where the incidence of postoperative nausea and/or vomiting is low. Launch Date1992 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
32.096 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00934180 |
8 mg single, oral dose: 8 mg route of administration: oral experiment type: single co-administered: |
ONDANSETRON plasma | Homo sapiens |
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30.196 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00934921 |
8 mg single, oral dose: 8 mg route of administration: oral experiment type: single co-administered: |
ONDANSETRON plasma | Homo sapiens |
|
26.2 ng/mL |
8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered: |
ONDANSETRON plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
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42.7 ng/mL |
8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered: |
ONDANSETRON plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
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125.8 ng/mL |
24 mg single, oral dose: 24 mg route of administration: Oral experiment type: SINGLE co-administered: |
ONDANSETRON plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
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194.4 ng/mL |
24 mg single, oral dose: 24 mg route of administration: Oral experiment type: SINGLE co-administered: |
ONDANSETRON plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
237.935 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00934180 |
8 mg single, oral dose: 8 mg route of administration: oral experiment type: single co-administered: |
ONDANSETRON plasma | Homo sapiens |
|
224.155 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00934180 |
8 mg single, oral dose: 8 mg route of administration: oral experiment type: single co-administered: |
ONDANSETRON plasma | Homo sapiens |
|
293.492 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00934921 |
8 mg single, oral dose: 8 mg route of administration: oral experiment type: single co-administered: |
ONDANSETRON plasma | Homo sapiens |
|
270.928 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00934921 |
8 mg single, oral dose: 8 mg route of administration: oral experiment type: single co-administered: |
ONDANSETRON plasma | Homo sapiens |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.1 h |
8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered: |
ONDANSETRON plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
3.5 h |
8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered: |
ONDANSETRON plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
4.7 h |
24 mg single, oral dose: 24 mg route of administration: Oral experiment type: SINGLE co-administered: |
ONDANSETRON plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
5.8 h |
24 mg single, oral dose: 24 mg route of administration: Oral experiment type: SINGLE co-administered: |
ONDANSETRON plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
27% |
8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered: |
ONDANSETRON plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no [IC50 >100 uM] | ||||
yes [IC50 0.15 uM] | yes (co-administration study) Comment: [PMID:23241029]: IC50 = 0.3 uM; Ondansetron treatment caused a statistically significantly higher Cmax of metformin compared with placebo and apparently decreased the renal clearance of metformin by 37% |
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yes [IC50 0.89 uM] | ||||
yes [IC50 17.4 uM] | ||||
yes [IC50 6.9 uM] | yes (co-administration study) Comment: [PMID:23241029]: IC50 = 0.16 uM; Ondansetron treatment caused a statistically significantly higher Cmax of metformin compared with placebo and apparently decreased the renal clearance of metformin by 37% |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes | ||||
yes | ||||
yes | likely (co-administration study) Comment: inducers or inhibitors of CYP1A2 may change the clearance and, hence, the half-life of ondansetron |
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yes | likely (co-administration study) Comment: inducers or inhibitors of CYP2D6 may change the clearance and, hence, the half-life of ondansetron |
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yes | yes (co-administration study) Comment: In patients treated with potent inducers of CYP3A4 (i.e., phenytoin, carbamazepine, and rifampin), the clearance of ondansetron was significantly increased and ondansetron blood concentrations were decreased. However, on the basis of available data, no dosage adjustment for ZOFRAN is recommended for patients on these drugs. |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
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Cardiorespiratory decompensation following methylprednisolone administration. | 1993 Jul-Sep |
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Extrapyramidal reaction caused by ondansetron. | 1994 Feb |
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Adjusting the dose of intravenous ondansetron plus dexamethasone to the emetogenic potential of the chemotherapy regimen. | 1995 Aug |
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The efficacy of prophylactic ondansetron, droperidol, perphenazine, and metoclopramide in the prevention of nausea and vomiting after major gynecologic surgery. | 1995 Jul |
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Inhibitory effect of ethanol on the 5-hydroxytryptamine-induced Bezold-Jarisch reflex--involvement of peripheral 5-HT3 receptors. | 1995 May 26 |
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A phase II study of ondansetron as antiemetic prophylaxis in patients receiving high-dose polychemotherapy and stem cell transplantation. | 1995 Sep |
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Nondepolarizing neuromuscular blockers inhibit the serotonin-type 3A receptor expressed in Xenopus oocytes. | 2000 Feb |
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Effect of the 5-HT3 receptor antagonist ondansetron on amphetamine-induced hyperactivity and stereotypy in rats. | 2000 Jul |
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Cloning, expression, and characterization of ferret 5-HT(3) receptor subunit. | 2000 Jul 7 |
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Randomized, double-blind, crossover, placebo-controlled trial of intravenous ondansetron for the prevention of intrathecal chemotherapy-induced vomiting in children. | 2001 Dec |
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Tropisetron vs ondansetron for prevention of postoperative nausea and vomiting after laparoscopic cholecystectomy: a randomized double-blind, placebo-controlled study. | 2002 Jul |
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Ondansetron inhibits the analgesic effects of tramadol: a possible 5-HT(3) spinal receptor involvement in acute pain in humans. | 2002 Jun |
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Ondansetron given in the acute withdrawal from a repeated cocaine sensitization dosing regimen reverses the expression of sensitization and inhibits self-administration. | 2002 Oct |
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Synthesis and structure-affinity relationships of novel N-(1-ethyl-4-methylhexahydro-1,4-diazepin-6-yl)pyridine-3-carboxamides with potent serotonin 5-HT3 and dopamine D2 receptor antagonistic activity. | 2003 Feb 27 |
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Involvement of some 5-HT receptors in methamphetamine-induced locomotor activity in mice. | 2004 Jun |
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Role of central 5-HT3 receptors in the control of blood pressure in stressed and non-stressed rats. | 2004 Nov 26 |
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Ondansetron, given during the acute cocaine withdrawal, attenuates oral cocaine self-administration. | 2004 Oct 25 |
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Ondansetron amelioration of scopolamine induced cognitive deficits in three-panel runway apparatus in rats. | 2004 Sep |
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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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The influence of dexamethasone in the decrease of chemotherapy-induced nausea and vomiting. | 2007 Apr-Jun |
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Reversal of cocaine-induced behavioral sensitization and associated phosphorylation of the NR2B and GluR1 subunits of the NMDA and AMPA receptors. | 2007 Feb |
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Interactions between metoclopramide and morphine: enhanced antinociception and motor dysfunction in rats. | 2007 Jan-Feb |
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Droperidol and ondansetron-induced QT interval prolongation: a clinical drug interaction study. | 2008 Aug |
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Comparative efficacy of maropitant and selected drugs in preventing emesis induced by centrally or peripherally acting emetogens in dogs. | 2008 Dec |
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Ondansetron-associated hypokalemia in a 2-year-old with pre-B-cell ALL. | 2008 Jan |
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Ondansetron given intravenously attenuates arterial blood pressure drop due to spinal anesthesia: a double-blind, placebo-controlled study. | 2008 Jul-Aug |
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Neonatal extrapyramidal movements. Neonatal withdrawal due to maternal citalopram and ondansetron use. | 2008 Mar |
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Ondansetron and seizures. | 2009 Dec |
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Coronary vasospasm and atrial fibrillation associated with ondansetron therapy. | 2009 Mar |
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Acute anti-emetic withdrawal associated with a hemorrhagic cerebellar arteriovenous malformation. | 2010 Aug |
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Ondansetron-induced headache in a parturient mimicking postdural puncture headache. | 2010 Feb |
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Multimodal prevention of pain, nausea and vomiting after breast cancer surgery. | 2010 Oct |
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Ondansetron-induced migraine-type headache. | 2010 Sep |
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Single-dose fosaprepitant for the prevention of chemotherapy-induced nausea and vomiting associated with cisplatin therapy: randomized, double-blind study protocol--EASE. | 2011 Apr 10 |
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In vivo assessment of antiemetic drugs and mechanism of lycorine-induced nausea and emesis. | 2011 Dec |
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Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | 2011 Jul 14 |
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Prophylaxis of radiation-induced nausea and vomiting using 5-hydroxytryptamine-3 serotonin receptor antagonists: a systematic review of randomized trials. | 2012 Jan 1 |
Sample Use Guides
To prevent nausea and vomiting associated with cancer chemotherapy the recommended adult oral dosage of ondansetron (ZOFRAN®) is a single 24-mg tablet administered 30 minutes before the start of single-day highly emetogenic chemotherapy; for moderately emetogenic cancer chemotherapy the recommended adult oral dosage is one 8-mg ondansetron (ZOFRAN®) tablet given twice a day (every 12 hours) for 1 to 2 days after completion of chemotherapy: the first dose should be administered 30 minutes before the start of emetogenic chemotherapy, with a subsequent dose 8 hours after the first dose.
To prevent nausea and vomiting associated with radiotherapy the recommended adult oral dosage is one 8-mg ondansetron (ZOFRAN®) tablet given 3 times a day; for total body irradiation, one 8-mg ondansetron (ZOFRAN®) tablet should be administered 1 to 2 hours before each fraction of radiotherapy administered each day; for single high-dose fraction radiotherapy to the abdomen, one 8-mg ondansetron (ZOFRAN®) tablet should be administered 1 to 2 hours before radiotherapy, with subsequent doses every 8 hours after the first dose for 1 to 2 days after completion of radiotherapy; for daily fractionated radiotherapy to the abdomen, one 8-mg ondansetron (ZOFRAN®) tablet should be administered 1 to 2 hours before radiotherapy, with subsequent doses every 8 hours after the first dose for each day radiotherapy is given.
To prevent postoperative nausea and vomiting the recommended adult oral dosage is 16 mg given as two 8-mg ondansetron (ZOFRAN®) tablets 1 hour before induction of anesthesia.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2969267
On the isolated vagus nerve and superior cervical ganglion of the rat, R,S-GR38032F (ondansetron) behaved as a reversible competitive antagonist of 5-HT-induced depolarization with pKB values of 8.61+/-0.08 (n=19) and 8.13+/-0.07 (n=16), respectively. The resolved R- and S-isomers of GR38032F were approximately equipotent as 5-HT antagonists on the rat vagus nerve: the pKB values were 8.95+/-0.05 (n=16) and 8.63+/-0.08 (n=17), respectively. R,S-GR38032F was also an effective antagonist of 5-HT on the rabbit isolated vagus nerve: in this case the pKB value was 9.40+/-0.14 (n=4).
Substance Class |
Chemical
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Record UNII |
4AF302ESOS
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Record Status |
Validated (UNII)
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Classification Tree | Code System | Code | ||
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WHO-ESSENTIAL MEDICINES LIST |
17.2
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WHO-ESSENTIAL MEDICINES LIST |
8.4
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LIVERTOX |
711
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NCI_THESAURUS |
C267
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NDF-RT |
N0000175818
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CFR |
21 CFR 216.24
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NDF-RT |
N0000175817
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WHO-VATC |
QA04AA01
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WHO-ATC |
A04AA01
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NCI_THESAURUS |
C94726
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FDA ORPHAN DRUG |
491115
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4AF302ESOS
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D017294
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757870
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1992
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8304
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m8213
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Ondansetron
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5965
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ONDANSETRON
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SUB09445MIG
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26225
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1478571
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99614-02-5
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4595
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2290
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DTXSID8023393
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CHEMBL46
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C1119
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DB00904
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4AF302ESOS
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Related Record | Type | Details | ||
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TARGET -> INHIBITOR | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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SALT/SOLVATE -> PARENT |
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
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METABOLIC ENZYME -> INHIBITOR |
IC50
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METABOLIC ENZYME -> SUBSTRATE | |||
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TARGET -> INHIBITOR |
IC50
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BINDER->LIGAND |
BINDING
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TRANSPORTER -> SUBSTRATE |
Related Record | Type | Details | ||
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METABOLITE INACTIVE -> PARENT | |||
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METABOLITE -> PARENT | |||
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METABOLITE ACTIVE -> PARENT |
Multiple P450 isoforms; Not found in plasma at concentrations likely to significantly contribute to the biological activity of ondansetron
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METABOLITE -> PARENT |
multiple CYP isoforms
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METABOLITE -> PARENT |
Multiple CYP isoforms
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METABOLITE -> PARENT |
Multiple CYP isoenzymes
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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Children <15 Years PHARMACOKINETIC |
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