Dolasetron

Base Information

• Chemical Name: Dolasetron
• CAS No.: 115956-12-2
• Molecular Formula: C₁₉H₂₀N₂O₃
• Molecular Weight: 324.379
• European Community (EC) Number: 601-402-4,601-404-5
• UNII: 82WI2L7Q6E
• DSSTox Substance ID: DTXSID4048276
• Wikipedia: Dolasetron
• Wikidata: Q1829318,Q27166396
• NCI Thesaurus Code: C61735
• RXCUI: 68091
• Pharos Ligand ID: UHCDNF4QXV1T,UHCQQX86RQ4A
• Metabolomics Workbench ID: 43057
• ChEMBL ID: CHEMBL2368925
• Mol file: 115956-12-2.mol

Synonyms:1H-indole-3-carboxylic acid, (6R,9AS)-octahydro-3-oxo-2,6-methano-2H-quinolizin-8-yl ester, rel-, methanesulfonate, hydrate (1:1:1);1H-indole-3-carboxylic acid, octahydro-3-oxo-2,6-methano-2H-quinolizin-8-yl ester, (2-alpha,6-alpha,8-alpha,9a-beta)-;1H-indole-3-carboxylic acid-trans-octahydro-3-oxo-2,6-methano-2H-quinolizin-8-yl ester methanesulfonate;Anzemet;dolasetron;dolasetron mesilate monohydrate;dolasetron mesylate;dolasetron mesylate monohydrate;indole-3-carboxylic acid, ester with (8R)-hexahydro-8-hydroxy-2,6-methano-2H-quinolizin-3(4H)-one;MDL 73,147EF;MDL 73147EF;MDL-73147EF;octahydro-3-oxo-2,6-methano-2H-quinolizin-8-yl 1H-indole-3-carboxylate

Chemical Property of Dolasetron

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 4.08E-10mmHg at 25°C
• Melting Point: 278 °C
• Refractive Index: 1.76
• Boiling Point: 535.1 °C at 760 mmHg
• PKA: 15.36±0.30(Predicted)
• Flash Point: 277.4 °C
• PSA: 62.40000
• Density: 1.37 g/cm³
• LogP: 2.45690
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Sparingly)
• Water Solubility.: Soluble
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 324.14739250
• Heavy Atom Count: 24
• Complexity: 535

Purity/Quality:

99% ^*data from raw suppliers

Dolasetron ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C2CC3CC(CC1N3CC2=O)OC(=O)C4=CNC5=CC=CC=C54
• Isomeric SMILES: C1[C@@H]2CC(C[C@H]3N2CC(=O)C1C3)OC(=O)C4=CNC5=CC=CC=C54
• Recent ClinicalTrials: The Pharmacokinetic Interaction Between Oral Casopitant and Oral Dolasetron, Granisetron or Rosiglitazone in Subjects
• Description: Dolasetron is an antagonist of the serotonin (5-HT) receptor subtype 5-HT3 (Ki = 20 nM). It is selective for 5-HT3 receptors over 5-HT1A, 5-HT1B, 5-HT2, dopamine D2, α1-, α2-, β-adrenergic, M1-5 muscarinic acetylcholine, and neurokinin-1 (NK1) receptors (IC50s = >10 μM for all). Dolasetron inhibits 5-HT-induced membrane currents in NG 108-15 cells (IC50 = 3.8 nM). It increases the latency to emesis and reduces the number of vomiting and retching episodes induced by cisplatin in ferrets when administered at doses of 0.5 or 2 mg/kg. Formulations containing dolasetron have been used in the prevention of postoperative or chemotherapy-induced nausea.
• Uses: prevention and treatment of postoperative nausea and vomiting Dolasetron is a bridged pseudopelletierine derivative; specific serotonin (5HT3) receptor antagonist.It is used as antiemetic. Bridged pseudopelletierine derivative; specific serotonin (5HT3) receptor antagonist. Antiemetic.

Technology Process of Dolasetron

There total 14 articles about Dolasetron 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: 98.0%

1H-indole-3-carboxylic acid (771-50-6) + endo-hexahydro-8-hydroxy-2,6-methano-2H-quinolizin-3(4H)-one (115956-07-5) → dolasetron (115956-12-2)

Guidance literature:

1H-indole-3-carboxylic acid; With trifluoroacetic acid; trifluoroacetic anhydride; In toluene; at 20 - 25 ℃; for 0.333333h;

endo-hexahydro-8-hydroxy-2,6-methano-2H-quinolizin-3(4H)-one; In toluene; at 30 - 35 ℃; for 2h;

With sodium carbonate; In water; toluene; Product distribution / selectivity;

Reference yield: 88.0%

endo-5-hydroxy-8-azatricyclo[5.3.1.03,8]-undecan-10-one (143343-85-5,115956-07-5) → indole-3-carboxylic acid octahydro-3-oxo-2,6-methano-2H-quinolizin-8-yl ester (139014-62-3,115956-12-2)

Guidance literature:

1H-indole-3-carboxylic acid; With trifluoroacetic anhydride; In dichloromethane; at 20 - 25 ℃; for 0.333333h;

endo-5-hydroxy-8-azatricyclo[5.3.1.0³,⁸]-undecan-10-one; dmap; In dichloromethane; at 30 - 35 ℃; for 4h;

With sodium hydrogencarbonate; In dichloromethane; water; Product distribution / selectivity;

Reference yield: 85.0%

1H-indole-3-carboxylic acid (771-50-6) + trans-hexahydro-8-hydroxy-2,6-methano-2H-quinolizin-3(4H)-one methanesulfonate → dolasetron (115956-12-2)

Guidance literature:

1H-indole-3-carboxylic acid; trans-hexahydro-8-hydroxy-2,6-methano-2H-quinolizin-3(4H)-one methanesulfonate; With oxalyl dichloride; In butanone; at 76 - 78 ℃; for 2.5h;

With potassium carbonate; In water; butanone; at 70 ℃;

upstream raw materials:

1H-indole-3-carboxylic acid

endo-hexahydro-8-hydroxy-2,6-methano-2H-quinolizin-3(4H)-one

endo-hexahydro-8-hydroxy-2.6-methano-2H-quinolizin-3(4H)-one

endo-5-hydroxy-8-azatricyclo[5.3.1.0³,⁸]-undecan-10-one

Downstream raw materials:

dolasetron mesylate

CH₄O₃S*C₁₉H₂₀N₂O₃

endo-hexahydro-8-(3-indolylcarbonyloxy)-2,6-methano-2H-quinolizin-3(4H)-one mesylate

endo-hexahydro-8-(3-indolylcarbonyloxy)-2,6-methano-2H-quinolizin-3(4H)-one methanesulphonate monohydrate

Refernces

• 1、 -. "Dolasetron oxide and preparation method and application thereof". Paragraph 0092-0094. . Retrieved 2020/05/14.
• 2、 -. "Polymorphs of Dolasetron base and process for preparation thereof". Page/Page column 6. . Retrieved 2009/02/11.