Ondansetron

Base Information

• Chemical Name: Ondansetron
• CAS No.: 99614-02-5
• Deprecated CAS: 108303-49-7,116002-70-1,116002-70-1,808754-64-5
• Molecular Formula: C₁₈H₁₉N₃O
• Molecular Weight: 293.368
• Hs Code.: 29339900
• European Community (EC) Number: 619-449-4
• UNII: 4AF302ESOS
• DSSTox Substance ID: DTXSID8023393
• Nikkaji Number: J245.610I
• Wikipedia: Ondansetron
• Wikidata: Q410011
• NCI Thesaurus Code: C1119
• RXCUI: 26225
• Pharos Ligand ID: BC9RKCW7SR4N
• Metabolomics Workbench ID: 38717
• ChEMBL ID: CHEMBL46
• Mol file: 99614-02-5.mol

Synonyms:4H-Carbazol-4-one, 1,2,3,9-tetrahydro-9-methyl-3-((2-methyl-1H-imidazol-1-yl)methyl)-;Dihydrate, Ondansetron Monohydrochloride;GR 38032F;GR-38032F;GR38032F;Hydrochloride, Ondansetron;Monohydrochloride Dihydrate, Ondansetron;Monohydrochloride, Ondansetron;ODT, Zofran;Ondansetron;Ondansetron Hydrochloride;Ondansetron Monohydrochloride;Ondansetron Monohydrochloride Dihydrate;Ondansetron, (+,-)-Isomer;Ondansetron, (R)-Isomer;Ondansetron, (S)-Isomer;SN 307;SN-307;SN307;Zofran;Zofran ODT

Chemical Property of Ondansetron

Chemical Property:

• Appearance/Colour: White or almost White Powder
• Melting Point: 231 - 232oC
• Refractive Index: 1.691
• Boiling Point: 546 °C at 760 mmHg
• PKA: pKa 7.4 (Uncertain)
• Flash Point: 284 °C
• PSA: 39.82000
• Density: 1.27 g/cm³
• LogP: 3.12850
• Storage Temp.: −20°C
• Solubility.: H2O: >5 mg/mL
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 293.152812238
• Heavy Atom Count: 22
• Complexity: 440

Purity/Quality:

99% ^*data from raw suppliers

Ondansetron ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,Xi
• Hazard Codes: T,Xi
• Statements: 25-36/37/38
• Safety Statements: 45-37/39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=NC=CN1CC2CCC3=C(C2=O)C4=CC=CC=C4N3C
• Recent ClinicalTrials: A Proof of Principle Study of Ondansetron for the Prevention of Vasovagal Syncope: The Eleventh Prevention of Syncope Trial (POST11)
• Recent EU Clinical Trials: A 24-Week, Multicenter, Randomized, Double-Blind, Placebo-Controlled, Parallel-Group, Phase 3 Clinical Study to Evaluate the Efficacy, Safety and Tolerability of AD04 (Ondansetron) in Adults with Alcohol Use Disorder (AUD) and Selected Polymorphisms in the Serotonin Transporter and Receptor Genes (ONWARD)
• Recent NIPH Clinical Trials: With ondansetron, comparison of desflurane and remimazolam besilate for the prevention of postoperative nausea and vomiting.
• Description: Ondansetron (hydrochloride) (CRM) (Item No. 21710) is a certified reference material categorized as an antiemetic. Formulations containing ondansetron have been used to reduce alcohol consumption and mood disturbances in early-onset alcoholics. This product is intended for research and forensic applications.
• Indications: Ondansetron (Zofran) is potent antagonists of 5-HT3 receptors,which is found peripherally on vagal nerve terminals and centrally in the CTZ. During chemotherapy that induces vomiting, mucosal enterochromaffin cells in the GI tract release serotonin, which stimulates 5-HT3 receptors.
• Clinical Use: Ondansetron
• Drug interactions: Potentially hazardous interactions with other drugs Cytotoxics: possible increased risk of ventricular arrhythmias with panobinostat and vandetanib. Dopaminergics: possible increased risk of hypotension with apomorphine - avoid.

Technology Process of Ondansetron

There total 28 articles about Ondansetron which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

2-methylimidazole (693-98-1) + 9-methyl-3-methylene-1,2,3,9-tetrahydro-4H-carbazol-4-one (99614-64-9) → ondanserton (99614-02-5,99614-58-1,99614-60-5,116002-70-1)

Guidance literature:

Montmorillonite K₁₀; In toluene; for 6h; Product distribution / selectivity; Heating / reflux;

Reference yield: 98.0%

N-(trimethylsilyl)-2-methylimidazole (60498-72-8) + 9-methyl-3-methylene-1,2,3,9-tetrahydro-4H-carbazol-4-one (99614-64-9) → ondanserton (99614-02-5,99614-58-1,99614-60-5,116002-70-1)

Guidance literature:

tetrabutyl ammonium fluoride; In acetonitrile; for 2.16667h; Product distribution / selectivity; Heating / reflux;

Reference yield: 92.0%

Ondansetron hydrochloride (99614-01-4,146475-23-2) → ondanserton (99614-02-5,99614-58-1,99614-60-5,116002-70-1)

Guidance literature:

With sodium hydroxide; In ethanol; water; Heating / reflux;

upstream raw materials:

2-methylimidazole

9-methyl-3-methylene-1,2,3,9-tetrahydro-4H-carbazol-4-one

9-methyl-1,2,3,9-tetrahydro-4H-carbazol-4-one

N-ethyloxazolidine

Downstream raw materials:

1,2,3,9-Tetrahydro-3-[(2-methyl-1H-imidazolyl-1-yl)methyl]-4H-carbazol-4-one

8-Hydroxyondansetron

9-methyl-3-methylene-1,2,3,9-tetrahydro-4H-carbazol-4-one

3-[(dimethylamino)methyl]-1,2,3,9-tetrahydro-9-methyl-4H-carbazol-4-one

Refernces

• 1、 -. "IMIDAZOLYL MODULATORS OF 5-HT3 RECEPTORS". . . Retrieved 2010/06/11.
• 2、 -. "A ONE-POT PROCESS FOR THE PREPARATION OF ANTIEMETIC AGENT, 1,2,3,9-TETRAHYDRO-9-METHYL-3[(2-METHYL)-1H-IMIDAZOLE-1-YL)METHYL]-4H-CARBAZOL-4-O". Page/Page column 18-19. . Retrieved 2008/06/13.