Synonym
GR 38032; GR-38032; GR38032; GR 38032X; Ondansetron
IUPAC/Chemical Name
4H-Carbazol-4-one, 1,2,3,9-tetrahydro-9-methyl-3-((2-methyl-1H-imidazol-1-yl)methyl)-
InChi Key
FELGMEQIXOGIFQ-UHFFFAOYSA-N
InChi Code
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
SMILES Code
O=C1C(CN2C=CN=C2C)CCC(N3C)=C1C4=C3C=CC=C4
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
The 5-HT3 receptors are present both peripherally on vagal nerve terminals and centrally in the chemoreceptor trigger zone of the area postrema in the medulla. Serotonin is released by the enterochromaffin cells of the small intestine in response to chemotherapeutic agents and may stimulate vagal afferents (via 5-HT3 receptors) to initiate the vomiting reflex. It is thought that ondansetron's antiemetic action is mediated mostly via antagonism of vagal afferents with a minor contribution from antagonism of central receptors.
Biological target:
Ondansetron(GR 38032; SN 307) is a serotonin 5-HT3 receptor antagonist.
In vitro activity:
In this study, the effect of 5-HT3 receptor antagonist, ondansetron, on BON was examined. Ondansetron did not affect growth of BON cells and also affected neither stimulation of phosphatidylinositol hydrolysis or inhibition of cyclic AMP production evoked by 5-HT in BON cells. Ondansetron, however, inhibited mobilization of intracellular calcium evoked by 5-HT.
Reference: Surg Oncol. 1993 Aug;2(4):221-5. https://pubmed.ncbi.nlm.nih.gov/8252212/
In vivo activity:
The present study assessed the effects of both acute and chronically administered ondansetron on auditory gating in DBA/2 mice. Auditory gating is defined as a decrease in amplitude of response to the second of a paired identical auditory stimulus presented 0.5 s following an initial auditory stimulus. Acute ondansetron administration at the lowest dose (0.1 mg/kg, IP) tested had no effect, while other doses (0.33 and 1 mg/kg, IP) produced improvements in auditory gating. The improvements were produced through both an increase in response to the first auditory stimulus and a decrease in the response to the second auditory stimulus.
Reference: Brain Res. 2009 Dec 1;1300:41-50. https://pubmed.ncbi.nlm.nih.gov/19728991/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
5.1 |
17.21 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
293.37
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Ishizuka J, Hsieh AC, Townsend CM Jr, Thompson JC. Effect of 5-HT3 receptor antagonist (ondansetron) on functioning human pancreatic carcinoid cells. Surg Oncol. 1993 Aug;2(4):221-5. doi: 10.1016/0960-7404(93)90010-v. PMID: 8252212.
2. Koulu M, Lappalainen J, Hietala J, Sjöholm B. Effects of chronic administration of ondansetron (GR38032F), a selective 5-HT3 receptor antagonist, on monoamine metabolism in mesolimbic and nigrostriatal dopaminergic neurons and on striatal D2-receptor binding. Psychopharmacology (Berl). 1990;101(2):168-71. doi: 10.1007/BF02244121. PMID: 2140903.
3. Wildeboer KM, Zheng L, Choo KS, Stevens KE. Ondansetron results in improved auditory gating in DBA/2 mice through a cholinergic mechanism. Brain Res. 2009 Dec 1;1300:41-50. doi: 10.1016/j.brainres.2009.08.075. Epub 2009 Sep 1. PMID: 19728991; PMCID: PMC2784252.
4. Khedhaier A, Ben Attia M, Gadacha W, Sani M, Bouzouita K, Chouchane L, Mechkouri M, Reinberg A, Boughattas NA. Circadian rhythms in toxic effects of the serotonin antagonist ondansetron in mice. Chronobiol Int. 2003 Nov;20(6):1103-16. doi: 10.1081/cbi-120025532. PMID: 14680146.
In vitro protocol:
1. Ishizuka J, Hsieh AC, Townsend CM Jr, Thompson JC. Effect of 5-HT3 receptor antagonist (ondansetron) on functioning human pancreatic carcinoid cells. Surg Oncol. 1993 Aug;2(4):221-5. doi: 10.1016/0960-7404(93)90010-v. PMID: 8252212.
2. Koulu M, Lappalainen J, Hietala J, Sjöholm B. Effects of chronic administration of ondansetron (GR38032F), a selective 5-HT3 receptor antagonist, on monoamine metabolism in mesolimbic and nigrostriatal dopaminergic neurons and on striatal D2-receptor binding. Psychopharmacology (Berl). 1990;101(2):168-71. doi: 10.1007/BF02244121. PMID: 2140903.
In vivo protocol:
1. Wildeboer KM, Zheng L, Choo KS, Stevens KE. Ondansetron results in improved auditory gating in DBA/2 mice through a cholinergic mechanism. Brain Res. 2009 Dec 1;1300:41-50. doi: 10.1016/j.brainres.2009.08.075. Epub 2009 Sep 1. PMID: 19728991; PMCID: PMC2784252.
2. Khedhaier A, Ben Attia M, Gadacha W, Sani M, Bouzouita K, Chouchane L, Mechkouri M, Reinberg A, Boughattas NA. Circadian rhythms in toxic effects of the serotonin antagonist ondansetron in mice. Chronobiol Int. 2003 Nov;20(6):1103-16. doi: 10.1081/cbi-120025532. PMID: 14680146.
1: Billio A, Morello E, Clarke MJ. Serotonin receptor antagonists for highly emetogenic chemotherapy in adults. Cochrane Database Syst Rev. 2010 Jan 20;(1):CD006272. Review. PubMed PMID: 20091591.
2: Frost F, Dailler F, Duflo F. [Ondansetron: a meta-analysis on its efficacy to prevent postoperative nausea and vomiting after craniotomy in adults and children]. Ann Fr Anesth Reanim. 2010 Jan;29(1):19-24. Epub 2010 Jan 15. French. PubMed PMID: 20080017.
3: Pikó B, Bassam A. [Treatment of tumor therapy-induced nausea and vomiting]. Magy Onkol. 2009 Mar;53(1):39-45. Review. Hungarian. PubMed PMID: 19318325.
4: Saito M, Aogi K, Sekine I, Yoshizawa H, Yanagita Y, Sakai H, Inoue K, Kitagawa C, Ogura T, Mitsuhashi S. Palonosetron plus dexamethasone versus granisetron plus dexamethasone for prevention of nausea and vomiting during chemotherapy: a double-blind, double-dummy, randomised, comparative phase III trial. Lancet Oncol. 2009 Feb;10(2):115-24. Epub 2009 Jan 8. Erratum in: Lancet Oncol. 2010 Mar;11(3)226. PubMed PMID: 19135415.
5: Reddy GK, Gralla RJ, Hesketh PJ. Novel neurokinin-1 antagonists as antiemetics for the treatment of chemotherapy-induced emesis. Support Cancer Ther. 2006 Apr 1;3(3):140-2. PubMed PMID: 18632487.
