Tandospirone

Base Information

• Chemical Name: Tandospirone
• CAS No.: 87760-53-0
• Molecular Formula: C21H29N5O2
• Molecular Weight: 383.494
• European Community (EC) Number: 685-029-2
• UNII: 190230I669
• DSSTox Substance ID: DTXSID6048836
• Nikkaji Number: J353.759E
• Wikipedia: Tandospirone
• Wikidata: Q6151362
• NCI Thesaurus Code: C87208
• Pharos Ligand ID: W8L4V9BB6GBS
• Metabolomics Workbench ID: 144600
• ChEMBL ID: CHEMBL274047
• Mol file: 87760-53-0.mol

Synonyms:3a,4,7,7a-hexahydro-2-(4-(4-(2-pyrimidinyl)-1-piperazinyl)butyl)-4,7-methano-1H-isoindole-1,3(2H)-dione;SM 3997;SM-3997;tandospirone

Chemical Property of Tandospirone

Chemical Property:

• Vapor Pressure: 5.23E-15mmHg at 25°C
• Melting Point: 112-113.5°
• Refractive Index: 1.589
• Boiling Point: 613.9 °C at 760 mmHg
• PKA: 7.71±0.10(Predicted)
• Flash Point: 325.1 °C
• PSA: 69.64000
• Density: 1.239g/cm³
• LogP: 1.35070
• Storage Temp.: Store at +4°C
• Solubility.: DMSO: soluble38mg/mL
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 383.23212518
• Heavy Atom Count: 28
• Complexity: 572

Purity/Quality:

99% ^*data from raw suppliers

Tandospirone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CC2CC1C3C2C(=O)N(C3=O)CCCCN4CCN(CC4)C5=NC=CC=N5
• Isomeric SMILES: C1C[C@H]2C[C@@H]1[C@H]3[C@@H]2C(=O)N(C3=O)CCCCN4CCN(CC4)C5=NC=CC=N5
• Recent ClinicalTrials: Comparison of Tandospirone, Amlodipine and Their Combination in Adults With Hypertension and Anxiety
• Recent EU Clinical Trials: The Safety and Efficacy of AL-8309B Ophthalmic Solution for the Treatment of
• Recent NIPH Clinical Trials: Effect of augmentation therapy with tandospirone on cognition and social function in schizophrenia
• Description: Tandospirone is another 5-HT1A receptor agonist under development by Sumitomo Pharmaceutical Co., Ltd., in Japan and Pfizer in the United States. Results of phase II and phase III clinical trials show that tandospirone is effective for the treatment of anxiety neurosis. Significant improvement is also observed in patients with psychosomatic disease, phobia, and depersonalization (Murasaki 1995). The results have shown that initial treatment should be started at 30 mg daily, and the dose should be increased up to 60 mg daily according to symptoms (Murasaki 1995). A double-blind comparative study with diazepam revealed that tandospirone tends to be superior to diazepam in patients with depressive neurosis, whereas diazepam may be more effective than tandospirone in severely ill patients (Murasaki et al. 1992).
• Uses: Tandospirone is a 5HT1A receptor partial agonist. Studies indicate that tandospirone significantly reduces haloperidol-induced bradykinesia in a dose dependent manner. The potency of Tandospirone is equal to that of buspirone and approximate one-half that of diazepam. The potency of Tandospirone at dopamine antagonistic action is less than 1/4 that of buspirone.

Technology Process of Tandospirone

There total 11 articles about Tandospirone 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: 88.6%

(1R*,2S*,3R*,4S*)-N-<4-<4-(2-Pyrimidinyl)-1-piperazinyl>-2-butynyl>-2,3-bicyclo<2.2.1>heptanedicarboximide (120596-77-2) → tandospirone (87760-53-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; for 1.5h; Ambient temperature;

DOI:10.1248/cpb.39.2288

Reference yield: 81.3%

N-(2-pyridinyl)piperazine (20980-22-7) + (1R,2S,3R,4S)-N-(4-bromobutyl)-2,3-bicyclo<2.2.1>heptanedicarboximide (99095-09-7) → tandospirone (87760-53-0)

Guidance literature:

With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 90 ℃; for 1h;

DOI:10.1248/cpb.39.2288

Reference yield: 59.0%

exo-bicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride (14166-28-0) + 1-(pyrimidin-2-yl)-4-(4-aminobutyl)piperazine (33386-20-8) → tandospirone (87760-53-0)

Guidance literature:

In pyridine; Heating;

DOI:10.1248/cpb.39.2288

upstream raw materials:

1,4-dibromo-butane

N-(2-pyridinyl)piperazine

(3aR,4S,7R,7aS)?4,7?methylene?1H?isoindole?1,3(2H)-dione

(1R,2S,3R,4S)-N-(4-bromobutyl)-2,3-bicyclo<2.2.1>heptanedicarboximide

Downstream raw materials:

tandospirone citrate

Refernces

• 1、 Ishizumi,Kojima,Antoku. "Synthesis and anxiolytic activity of N-substituted cyclic imides (1R*,2S*3R*,4S*)-N-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-2,3-b icyclo[2.2.1]heptanedicarboxime (Tandospirone) and related compounds". . p. 2288 - 2300. Retrieved 2007/10/02.