Ondansetron HCl hydrate | CAS#99614-02-5 | 5-HT2 inhibitor

MedKoo Cat#: 100676 | Name: Ondansetron HCl hydrate

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ondansetron is a highly selective serotonin 5-HT3 receptor antagonist, with low affinity for dopamine receptors. It is effective in the treatment of nausea and vomiting caused by cytotoxic chemotherapy drugs, including cisplatin, and has reported anxiolytic and neuroleptic properties. in vitro studies confirm that Ondansetron inhibits AChE and BChE by non-competitive and mixed inhibition, respectively, with IC50 values 33 µM (AChE) and 2.5 µM (BChE). Ondansetron showed activity for preventing of ovarian hyperstimulation syndrome

Chemical Structure

Ondansetron HCl hydrate

CAS#103639-04-9 (HCl hydrate),

Theoretical Analysis

MedKoo Cat#: 100676

Name: Ondansetron HCl hydrate

CAS#: 103639-04-9 (HCl hydrate),

Chemical Formula: C18H24ClN3O3

Exact Mass: 365.1506

Molecular Weight: 365.86

Elemental Analysis: C, 59.09; H, 6.61; Cl, 9.69; N, 11.49; O, 13.12

Price and Availability

Size	Price	Availability	Quantity
1g	USD 400.00	2 Weeks
5g	USD 700.00	2 Weeks

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Related CAS #

99614-02-5 (free base) 99614-01-4 (HCl) 103639-04-9 (HCl hydrate)

Synonym

GR 38032F; GR-38032F;GR38032F;GRC50775; GRC-50775; GRC 50775; SN307; Ondansetron HCl hydrate

IUPAC/Chemical Name

1, 2, 3, 9-tetrahydro-9-methyl-3-[(2-methyl-1H-imidazol-1- yl)methyl]-4H-carbazol-4-one, monohydrochloride, dihydrate

InChi Key

VRSLTNZJOUZKLX-UHFFFAOYSA-N

InChi Code

InChI=1S/C18H19N3O.ClH.2H2O/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;1H;2*1H2

SMILES Code

O=C1C(CN2C=CN=C2C)CCC(N3C)=C1C4=C3C=CC=C4.[H]Cl.[H]O[H].[H]O[H]

Appearance

Solid powder

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, not in water

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.

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Ondansetron (GR 38032) hydrochloride dehydrate is an orally active, highly selective and competitive 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
	DMF	10.0	27.33
	DMSO	60.0	164.00
	DMSO:PBS (pH 7.2) (1:4)	0.2	0.55
	Ethanol	0.5	1.37
	Water	16.7	45.56

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 365.86 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:

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: Gholami A, Minai-Tehrani D, Eriksson LA. In silico and in vitro studies confirm Ondansetron as a novel acetylcholinesterase and butyrylcholinesterase inhibitor. Sci Rep. 2023 Jan 12;13(1):643. doi: 10.1038/s41598-022-27149-z. PMID: 36635365; PMCID: PMC9837033. 2: Mehta MV, Chudasama PA, Baria T. To Compare the Effectiveness of Granisetron Versus Ondansetron to Control Nausea and Vomiting During Lower Segment Cesarean Section Under Subarachnoid Block. Anesth Essays Res. 2022 Jul-Sep;16(3):378-380. doi: 10.4103/aer.aer_86_22. Epub 2022 Dec 9. PMID: 36620101; PMCID: PMC9813993. 3: Bakırcı Ş, Sağsöz N, Devrim T, Şahin Y, Bulanık M, Gözüyukarı H. Effect of ondansetron for preventing of ovarian hyperstimulation syndrome: in an experimental rat model. Gynecol Endocrinol. 2022 Dec 29:1-4. doi: 10.1080/09513590.2022.2163233. Epub ahead of print. PMID: 36579847. 4: Firew E, Huang H, Anand A, Asfaw YA, Parikh C, Khan HR. Ondansetron-induced pseudoallergy with non-ischemic myocardial injury: A rare case report of Kounis syndrome. Clin Case Rep. 2022 Dec 22;10(12):e6781. doi: 10.1002/ccr3.6781. PMID: 36578798; PMCID: PMC9780426. 5: Li H, Jia Y, Liu C. Retraction notice to "Pluronic® F127 stabilized reduced graphene oxide hydrogel for transdermal delivery of ondansetron: Ex vivo and animal studies" [Colloids Surf. B Biointerfaces, 195, (2020), 111259]. Colloids Surf B Biointerfaces. 2022 Dec 24;222:113062. doi: 10.1016/j.colsurfb.2022.113062. Epub ahead of print. PMID: 36571979. 6: Hou XM, Chen YJ, Lai L, Liu K, Shen QH. Ondansetron Reduces the Incidence of Hypotension after Spinal Anaesthesia: A Systematic Review and Meta-Analysis. Pharmaceuticals (Basel). 2022 Dec 19;15(12):1588. doi: 10.3390/ph15121588. PMID: 36559039; PMCID: PMC9787671. 7: Mansour M, Nasr M, Ahmed-Farid OAH, Ahmed RF. Intranasal ondansetron microemulsion counteracting the adverse effects of cisplatin: animal study. Pharmacol Rep. 2022 Dec 14. doi: 10.1007/s43440-022-00435-3. Epub ahead of print. PMID: 36517694. 8: Abdulhussain AS. Combination of dexamethasone and ondansetron in prophylaxis nausea and vomiting in gynecological operation. J Popul Ther Clin Pharmacol. 2022 Dec 3;29(4):e150-e157. doi: 10.47750/jptcp.2022.984. PMID: 36464494. 9: Ali HG, ELatief NA. Comparison of Prophylactic Phenylephrine Infusion Versus Intravenous Ondansetron on Hypotension During Spinal Anesthesia for Cesarean Section. Anesth Essays Res. 2022 Apr-Jun;16(2):226-230. doi: 10.4103/aer.aer_48_22. Epub 2022 Sep 19. PMID: 36447915; PMCID: PMC9701336. 10: Reis ACC, Jorge BC, Stein J, Moreira SDS, Manoel BM, Aquino AM, Valente LC, Kassuya CAL, Scarano WR, Arena AC. Safety evaluation of ondansetron after gestational exposure on male reproductive parameters in rats. Regul Toxicol Pharmacol. 2023 Jan;137:105302. doi: 10.1016/j.yrtph.2022.105302. Epub 2022 Nov 26. PMID: 36442580. 11: Rezvani Kakhki B, Ghasemi T, Vafadar Moradi E, Abbasi Shaye Z, Mousavi SM. Aromatherapy with Isopropyl Alcohol versus Intravenous Ondansetron in Management of Mild Brain Trauma Nausea and Vomiting; a Randomized Clinical Trial. Arch Acad Emerg Med. 2022 Oct 31;10(1):e87. doi: 10.22037/aaem.v10i1.1792. PMID: 36426172; PMCID: PMC9676696. 12: Shayan M, Eslami F, Khosravi A, Rashidian A, Jafari RM, Maroufi SF, Golroudbari HT, Dehpour AR. The Possible Protective Effects of Ondansetron and Tropisetron on Optic Nerve Crush Injury in Rats. Drug Res (Stuttg). 2022 Nov 24. doi: 10.1055/a-1969-4600. Epub ahead of print. PMID: 36423625. 13: Feiz Disfani H, Kamandi M, Hoseini SB, Shirazi N, Panahi M. Nausea control in mild head trauma patients: Effectiveness of metoclopramide and ondansetron in the emergency department in a double-blind study. Caspian J Intern Med. 2022 Fall;13(4):699-704. doi: 10.22088/cjim.13.4.699. PMID: 36420343; PMCID: PMC9659822. 14: Black K, Brenn BR, Gaedigk A, Wanderer JP, Van Driest SL. Pediatric CYP2D6 metabolizer status and post-tonsillectomy nausea and vomiting after ondansetron. Clin Transl Sci. 2022 Nov 9. doi: 10.1111/cts.13447. Epub ahead of print. PMID: 36350309. 15: Wu M, Cheng Z, Le AT, Tan Y, Peltz G. Optimizing a therapy for opiate use disorders: Characterizing ondansetron pharmacokinetics in blood and brain. Clin Transl Sci. 2022 Oct 28. doi: 10.1111/cts.13440. Epub ahead of print. PMID: 36305236. 16: Vashishth S, Lal J, Bangarwa N, Wadhwani J, Smriti M. Efficacy of Variable Doses of Prophylactic Intravenous Ondansetron in Attenuating Spinal Induced Hypotension in Parturients Undergoing Caesarean Delivery: A Randomised Control Trial. Cureus. 2022 Sep 22;14(9):e29440. doi: 10.7759/cureus.29440. PMID: 36299981; PMCID: PMC9587515. 17: Wongyingsinn M, Peanpanich P, Charoensawan S. A randomized controlled trial comparing incidences of postoperative nausea and vomiting after laparoscopic cholecystectomy for preoperative intravenous fluid loading, ondansetron, and control groups in a regional hospital setting in a developing country. Medicine (Baltimore). 2022 Oct 21;101(42):e31155. doi: 10.1097/MD.0000000000031155. PMID: 36281094; PMCID: PMC9592396. 18: Das S, Kumar A, Gupta A, Kumar A. A Randomised Controlled Trial to Compare the Effect of Ramosetron and Ondansetron in Prevention of Postoperative Nausea and Vomiting in Patients Undergoing Laparoscopic Gynaecological Procedures. Cureus. 2022 Sep 15;14(9):e29200. doi: 10.7759/cureus.29200. PMID: 36258972; PMCID: PMC9569150. 19: Somsundar RG, Shivakumar G, Santhosh MCB, Krishna K. A Comparative Clinical Study of Methylprednisolone with Ondansetron versus Ramosetron in Preventing Postoperative Nausea and Vomiting in Patients Undergoing Middle-Ear Surgeries. Anesth Essays Res. 2022 Jan-Mar;16(1):60-64. doi: 10.4103/aer.aer_2_22. Epub 2022 Jun 27. PMID: 36249137; PMCID: PMC9558658. 20: Li C, Cui W, Song P, Liu W, Wang X, Yang Q. Effect of ondansetron for preventing postoperative nausea and vomiting after breast cancer surgery. Am J Transl Res. 2022 Sep 15;14(9):6689-6695. PMID: 36247242; PMCID: PMC9556477.