Basic information
- CAS
87760-53-0- Standard SMILES
O=C1[C@@H]2[C@H]3CC[C@H](C3)[C@@H]2C(=O)N1CCCCN1CCN(c2ncccn2)CC1- InChIKey
CEIJFEGBUDEYSX-FZDBZEDMSA-N- Molecular formula
- C21H29N5O2
- Average molar mass
- 383.5 g/mol
- Monoisotopic mass
- 383.23212518
Overview
Tandospirone is a dicarboximide that is (3aR,4S,7R,7aS)-hexahydro-1H-4,7-methanoisoindole-1,3(2H)-dione which is substituted by a 4-[4-(pyrimidin-2-yl)piperazin-1-yl]butyl group at position 2. It is a potent and selective 5-HT1A receptor partial agonist (Ki = 27 nM). It has a role as an antidepressant and an anxiolytic drug. It is a dicarboximide, a bridged compound, a member of pyrimidines, a N-alkylpiperazine and a N-arylpiperazine. It is a conjugate base of a tandospirone(1+).
Names & identifiers
- Preferred name
- Tandospirone
- IUPAC
- (1S,2R,6S,7R)-4-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]-4-azatricyclo[5.2.1.02,6]decane-3,5-dione
- English name
- Tandospirone
- Molecular formula
- C21H29N5O2
- Molecular weight
- 383.49
Names & synonyms
Tandospirone87760-53-0tandospironatandospironumDTXSID6048836DTXCID3028762CHEBI:145673190230I669SM-3997(1R*,2S*,3R*,4S*)-N-(4-(4-(2-PYRIMIDINYL)-1-PIPERAZINYL)BUTYL)-2,3-NORBORNANEDICARBOXIMIDE(1R,2S,6R,7S)-4-(4-(4-(pyrimidin-2-yl)piperazin-1-yl)butyl)-4-azatricyclo(5.2.1.0^(2,6))decane-3,5-dione(1R,2S,6R,7S)-4-{4-[4-(pyrimidin-2-yl)piperazin-1-yl]butyl}-4-azatricyclo[5.2.1.0^{2,6}]decane-3,5-dione
Show more names
Sediel(3aR,4S,7R,7aS)-rel-Tandospirone (SM3997)Tandospirone [inn:ban]TANDOSPIRONE USP/EP/BPTandospirone hydrochloride(1R*,2S*,3R*,4S*)-N-(4-(4-(2-Pyrimidinyl)-1-piperazinyl)butyl)-2,3-norbornanedicarboximide citrate salt
(1S,2R,6S,7R)-4-(4-(4-Pyrimidin-2-yl-piperazin-1-yl)-butyl)-4-aza-tricyclo(5.2.1.0*2,6*)decane-3,5-dione(1S,2R,6S,7R)-4-[4-(4-Pyrimidin-2-yl-piperazin-1-yl)-butyl]-4-aza-tricyclo[5.2.1.0*2,6*]decane-3,5-dioneRefChem:1873773a,4,7,7a-hexahydro-2-(4-(4-(2-pyrimidinyl)-1-piperazinyl)butyl)-4,7-methano-1H-isoindole-1,3(2H)-dione4,7-Methano-1H-Isoindole-1,3(2h)-Dione, Hexahydro-2-(4-(4-(2-Pyrimidinyl)-1-Piperazinyl)Butyl)-, (3a-Alpha,4Beta,7Beta,7a-Alpha)-685-029-2MFCD00904852(3aR,4S,7R,7aS)-2-(4-(4-(pyrimidin-2-yl)piperazin-1-yl)butyl)hexahydro-1H-4,7-methanoisoindole-1,3(2H)-dione
Properties
Computed structural properties
- XLogP
- 1.9
- Topological polar surface area
- 69.6 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 6
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 572
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Physicochemical properties
- Melting point
- 112 · 112-113.5°
- Boiling point
- 613.9 · 613.9±65.0 °C(Predicted)
- Density
- 1.239 · 1.239±0.06 g/cm3(Predicted)
- storage temp.
- 4 °C · Store at +4°C
- solubility
- 38 mg/mL · DMSO: soluble38mg/mL
- pka
- 7.71 · 7.71±0.10(Predicted)
- form
- Solid
- color
- White to Off-White
- InChI
- 1S/C21H29N5O2/c27-19-17-15-4-5-16(14-15)18(17)20(28)26(19)9-2-1-8-24-10-12-25(13-11-24)21-22-6-3-7-23-21/h3,6-7,15-18H,1-2,4-5,8-14H2/t15-,16+,17+,18-
- InChIKey
- CEIJFEGBUDEYSX-FZDBZEDMSA-N
- SMILES
- O=C1[C@@H]2[C@H]3CC[C@H](C3)[C@@H]2C(=O)N1CCCCN4CCN(CC4)c5ncccn5
- FDA UNII
- 190230 I669 · 190230I669
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Toxicology
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Tandospirone
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
Safety data
- wgk
- 3
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P305+P351+P338
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Agents that alleviate ANXIETY, tension, and ANXIETY DISORDERS, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions. ADRENERGIC BETA-ANTAGONISTS are commonly used in the symptomatic treatment of anxiety but are not included here.
Endogenous compounds and drugs that bind to and activate SEROTONIN RECEPTORS. Many serotonin receptor agonists are used as ANTIDEPRESSANTS; ANXIOLYTICS; and in the treatment of MIGRAINE DISORDERS.
Applications
DescriptionTandospirone 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).
UsesTandospirone 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.
Preparation methods
PreparationTandospirone is attained from the exo diels-alder adduct of maleic anhydride and cyclopentadiene in a four step convergent approach.
Upstream & downstream products
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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