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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
Structure of ONDANSETRON

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

HIDE SMILES / InChI

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 ( + / - )

Description
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.

Originator

Curator's Comment: Glaxo Wellcome is a predecessor of GlaxoSmithKline plc.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
8.31 null [pKi]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
ZOFRAN

Approved Use

Prevention 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 Date

1992
Preventing
ZOFRAN

Approved Use

Prevention 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 Date

1992
Preventing
ZOFRAN

Approved Use

Prevention 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 Date

1992
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
32.096 ng/mL
8 mg single, oral
dose: 8 mg
route of administration: oral
experiment type: single
co-administered:
ONDANSETRON plasma
Homo sapiens
30.196 ng/mL
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
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
237.935 ng*h/mL
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
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
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
8 mg single, oral
dose: 8 mg
route of administration: oral
experiment type: single
co-administered:
ONDANSETRON plasma
Homo sapiens
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Funbound

ValueDoseCo-administeredAnalytePopulation
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

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer








Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical 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%
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

Drug as victim

TargetModalityActivityMetaboliteClinical 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
yes
likely (co-administration study)
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

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Cardiorespiratory decompensation following methylprednisolone administration.
1993 Jul-Sep
Extrapyramidal reaction caused by ondansetron.
1994 Feb
Adjusting the dose of intravenous ondansetron plus dexamethasone to the emetogenic potential of the chemotherapy regimen.
1995 Aug
The efficacy of prophylactic ondansetron, droperidol, perphenazine, and metoclopramide in the prevention of nausea and vomiting after major gynecologic surgery.
1995 Jul
Inhibitory effect of ethanol on the 5-hydroxytryptamine-induced Bezold-Jarisch reflex--involvement of peripheral 5-HT3 receptors.
1995 May 26
A phase II study of ondansetron as antiemetic prophylaxis in patients receiving high-dose polychemotherapy and stem cell transplantation.
1995 Sep
Nondepolarizing neuromuscular blockers inhibit the serotonin-type 3A receptor expressed in Xenopus oocytes.
2000 Feb
Effect of the 5-HT3 receptor antagonist ondansetron on amphetamine-induced hyperactivity and stereotypy in rats.
2000 Jul
Cloning, expression, and characterization of ferret 5-HT(3) receptor subunit.
2000 Jul 7
Randomized, double-blind, crossover, placebo-controlled trial of intravenous ondansetron for the prevention of intrathecal chemotherapy-induced vomiting in children.
2001 Dec
Tropisetron vs ondansetron for prevention of postoperative nausea and vomiting after laparoscopic cholecystectomy: a randomized double-blind, placebo-controlled study.
2002 Jul
Ondansetron inhibits the analgesic effects of tramadol: a possible 5-HT(3) spinal receptor involvement in acute pain in humans.
2002 Jun
Ondansetron given in the acute withdrawal from a repeated cocaine sensitization dosing regimen reverses the expression of sensitization and inhibits self-administration.
2002 Oct
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
Involvement of some 5-HT receptors in methamphetamine-induced locomotor activity in mice.
2004 Jun
Role of central 5-HT3 receptors in the control of blood pressure in stressed and non-stressed rats.
2004 Nov 26
Ondansetron, given during the acute cocaine withdrawal, attenuates oral cocaine self-administration.
2004 Oct 25
Ondansetron amelioration of scopolamine induced cognitive deficits in three-panel runway apparatus in rats.
2004 Sep
Selective serotonin 5-HT3 receptor antagonists for postoperative nausea and vomiting: are they all the same?
2005
The influence of dexamethasone in the decrease of chemotherapy-induced nausea and vomiting.
2007 Apr-Jun
Reversal of cocaine-induced behavioral sensitization and associated phosphorylation of the NR2B and GluR1 subunits of the NMDA and AMPA receptors.
2007 Feb
Interactions between metoclopramide and morphine: enhanced antinociception and motor dysfunction in rats.
2007 Jan-Feb
Droperidol and ondansetron-induced QT interval prolongation: a clinical drug interaction study.
2008 Aug
Comparative efficacy of maropitant and selected drugs in preventing emesis induced by centrally or peripherally acting emetogens in dogs.
2008 Dec
Ondansetron-associated hypokalemia in a 2-year-old with pre-B-cell ALL.
2008 Jan
Ondansetron given intravenously attenuates arterial blood pressure drop due to spinal anesthesia: a double-blind, placebo-controlled study.
2008 Jul-Aug
Neonatal extrapyramidal movements. Neonatal withdrawal due to maternal citalopram and ondansetron use.
2008 Mar
Ondansetron and seizures.
2009 Dec
Coronary vasospasm and atrial fibrillation associated with ondansetron therapy.
2009 Mar
Acute anti-emetic withdrawal associated with a hemorrhagic cerebellar arteriovenous malformation.
2010 Aug
Ondansetron-induced headache in a parturient mimicking postdural puncture headache.
2010 Feb
Multimodal prevention of pain, nausea and vomiting after breast cancer surgery.
2010 Oct
Ondansetron-induced migraine-type headache.
2010 Sep
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
In vivo assessment of antiemetic drugs and mechanism of lycorine-induced nausea and emesis.
2011 Dec
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011 Jul 14
Prophylaxis of radiation-induced nausea and vomiting using 5-hydroxytryptamine-3 serotonin receptor antagonists: a systematic review of randomized trials.
2012 Jan 1
Patents

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
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
Created
by admin
on Mon Mar 31 19:36:59 GMT 2025
Edited
by admin
on Mon Mar 31 19:36:59 GMT 2025
Record UNII
4AF302ESOS
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
A04AA01
Preferred Name English
ONDANSETRON
INN   JAN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
INN  
Official Name English
ONDANSETRON [MI]
Common Name English
(±)-2,3-DIHYDRO-9-METHYL-3-((2-METHYLIMIDAZOL-1-YL)METHYL)CARBAZOL-4(1H)-ONE
Systematic Name English
ONDANSETRON [MART.]
Common Name English
EUR-1025
Code English
ondansetron [INN]
Common Name English
4H-CARBAZOL-4-ONE, 1,2,3,9-TETRAHYDRO-9-METHYL-3-((2-METHYL-1H-IMIDAZOL-1-YL)METHYL)- (±)-
Systematic Name English
NSC-757870
Code English
ONDANSETRON [VANDF]
Common Name English
ONDANSETRON [USP MONOGRAPH]
Common Name English
ZOFRAN ODT
Brand Name English
ONDANSETRON [ORANGE BOOK]
Common Name English
ONDANSETRON [JAN]
Common Name English
Ondansetron [WHO-DD]
Common Name English
ONDANSETRON [USP-RS]
Common Name English
Classification Tree Code System Code
WHO-ESSENTIAL MEDICINES LIST 17.2
Created by admin on Mon Mar 31 19:36:59 GMT 2025 , Edited by admin on Mon Mar 31 19:36:59 GMT 2025
WHO-ESSENTIAL MEDICINES LIST 8.4
Created by admin on Mon Mar 31 19:36:59 GMT 2025 , Edited by admin on Mon Mar 31 19:36:59 GMT 2025
LIVERTOX 711
Created by admin on Mon Mar 31 19:36:59 GMT 2025 , Edited by admin on Mon Mar 31 19:36:59 GMT 2025
NCI_THESAURUS C267
Created by admin on Mon Mar 31 19:36:59 GMT 2025 , Edited by admin on Mon Mar 31 19:36:59 GMT 2025
NDF-RT N0000175818
Created by admin on Mon Mar 31 19:36:59 GMT 2025 , Edited by admin on Mon Mar 31 19:36:59 GMT 2025
CFR 21 CFR 216.24
Created by admin on Mon Mar 31 19:36:59 GMT 2025 , Edited by admin on Mon Mar 31 19:36:59 GMT 2025
NDF-RT N0000175817
Created by admin on Mon Mar 31 19:36:59 GMT 2025 , Edited by admin on Mon Mar 31 19:36:59 GMT 2025
WHO-VATC QA04AA01
Created by admin on Mon Mar 31 19:36:59 GMT 2025 , Edited by admin on Mon Mar 31 19:36:59 GMT 2025
WHO-ATC A04AA01
Created by admin on Mon Mar 31 19:36:59 GMT 2025 , Edited by admin on Mon Mar 31 19:36:59 GMT 2025
NCI_THESAURUS C94726
Created by admin on Mon Mar 31 19:36:59 GMT 2025 , Edited by admin on Mon Mar 31 19:36:59 GMT 2025
FDA ORPHAN DRUG 491115
Created by admin on Mon Mar 31 19:36:59 GMT 2025 , Edited by admin on Mon Mar 31 19:36:59 GMT 2025
Code System Code Type Description
FDA UNII
4AF302ESOS
Created by admin on Mon Mar 31 19:36:59 GMT 2025 , Edited by admin on Mon Mar 31 19:36:59 GMT 2025
PRIMARY
MESH
D017294
Created by admin on Mon Mar 31 19:36:59 GMT 2025 , Edited by admin on Mon Mar 31 19:36:59 GMT 2025
PRIMARY
NSC
757870
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PRIMARY
DRUG CENTRAL
1992
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PRIMARY
HSDB
8304
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PRIMARY
MERCK INDEX
m8213
Created by admin on Mon Mar 31 19:36:59 GMT 2025 , Edited by admin on Mon Mar 31 19:36:59 GMT 2025
PRIMARY Merck Index
LACTMED
Ondansetron
Created by admin on Mon Mar 31 19:36:59 GMT 2025 , Edited by admin on Mon Mar 31 19:36:59 GMT 2025
PRIMARY
INN
5965
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PRIMARY
WIKIPEDIA
ONDANSETRON
Created by admin on Mon Mar 31 19:36:59 GMT 2025 , Edited by admin on Mon Mar 31 19:36:59 GMT 2025
PRIMARY
EVMPD
SUB09445MIG
Created by admin on Mon Mar 31 19:36:59 GMT 2025 , Edited by admin on Mon Mar 31 19:36:59 GMT 2025
PRIMARY
RXCUI
26225
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PRIMARY RxNorm
RS_ITEM_NUM
1478571
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PRIMARY
CAS
99614-02-5
Created by admin on Mon Mar 31 19:36:59 GMT 2025 , Edited by admin on Mon Mar 31 19:36:59 GMT 2025
SUPERSEDED
PUBCHEM
4595
Created by admin on Mon Mar 31 19:36:59 GMT 2025 , Edited by admin on Mon Mar 31 19:36:59 GMT 2025
PRIMARY
IUPHAR
2290
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PRIMARY
EPA CompTox
DTXSID8023393
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PRIMARY
ChEMBL
CHEMBL46
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PRIMARY
NCI_THESAURUS
C1119
Created by admin on Mon Mar 31 19:36:59 GMT 2025 , Edited by admin on Mon Mar 31 19:36:59 GMT 2025
PRIMARY
DRUG BANK
DB00904
Created by admin on Mon Mar 31 19:36:59 GMT 2025 , Edited by admin on Mon Mar 31 19:36:59 GMT 2025
PRIMARY
DAILYMED
4AF302ESOS
Created by admin on Mon Mar 31 19:36:59 GMT 2025 , Edited by admin on Mon Mar 31 19:36:59 GMT 2025
PRIMARY
CAS
99614-02-5
Created by admin on Mon Mar 31 19:36:59 GMT 2025 , Edited by admin on Mon Mar 31 19:36:59 GMT 2025
PRIMARY
SMS_ID
100000092334
Created by admin on Mon Mar 31 19:36:59 GMT 2025 , Edited by admin on Mon Mar 31 19:36:59 GMT 2025
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
METABOLIC ENZYME -> SUBSTRATE
SALT/SOLVATE -> PARENT
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
METABOLIC ENZYME -> INHIBITOR
IC50
METABOLIC ENZYME -> SUBSTRATE
TARGET -> INHIBITOR
IC50
BINDER->LIGAND
BINDING
TRANSPORTER -> SUBSTRATE
Related Record Type Details
METABOLITE INACTIVE -> PARENT
METABOLITE -> PARENT
METABOLITE ACTIVE -> PARENT
Multiple P450 isoforms; Not found in plasma at concentrations likely to significantly contribute to the biological activity of ondansetron
METABOLITE -> PARENT
multiple CYP isoforms
METABOLITE -> PARENT
Multiple CYP isoforms
METABOLITE -> PARENT
Multiple CYP isoenzymes
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC Children <15 Years
PHARMACOKINETIC