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Details

Stereochemistry ACHIRAL
Molecular Formula C21H29N5O2
Molecular Weight 383.4881
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TANDOSPIRONE

SMILES

C(CCN1C(=O)[C@]2([H])[C@@]3([H])CC[C@]([H])(C3)[C@]2([H])C1=O)CN4CCN(CC4)c5ncccn5

InChI

InChIKey=CEIJFEGBUDEYSX-FZDBZEDMSA-N
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-

HIDE SMILES / InChI

Molecular Formula C21H29N5O2
Molecular Weight 383.4881
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/17516698| https://www.ncbi.nlm.nih.gov/pubmed/11579010

Sediel (generic name: tandospirone citrate, marketed as Sediel in Japan) is a new type of antianxiety drug developed independently by Sumitomo Pharmaceuticals. It acts selectively on only the serotonin nerves in the brain that play an important part in the formation of anxiety and depression, and demonstrates antianxiety and anti-depression effects. Since it does not act on the other nerves that are so extensive in the brain, there is virtually no hypnotic or sedative effect, and the drug displays virtually no drug-dependence or side effects such as drowsiness and dizziness. Sediel has been on sale in Japan since December 1996, and is recognized for recognized as effective in the treatment of generalized anxiety disorders. Tandospirone acts as a potent and selective 5-HT1A receptor partial agonist. It was also investigated the usefulness of 5-HT1A agonists for enhancing some types of cognitive performance and possibly social and work function in patients with schizophrenia, and related to this was discovered, that tandospirone in combination with atypical antipsychotic drugs can improve cognitive function in Schizophrenia.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
27.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Sediel

Approved Use

Unknown

Launch Date

1.07239683E12
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Agonist and antagonist actions of antipsychotic agents at 5-HT1A receptors: a [35S]GTPgammaS binding study.
1998 Aug 21
Patents

Patents

Sample Use Guides

oral, 30 mg/day
Route of Administration: Oral
In Vitro Use Guide
Under voltage-clamp conditions, tandospirone (TDS) (3*10(-7) M) induced an inward rectifying K+ current in a concentration-dependent manner. In the inside-out patch recording mode, TDS-activated single K+ channel currents (iTDS) which also showed an inward rectification. When the GDP in cytosolic side was completely replaced with GTP, the open probability of iTDS significantly increased. These results indicate that the activation of 5-HT1A receptors by TDS directly opens the inward rectifying K+ channels via a G-protein mediated process.
Substance Class Chemical
Created
by admin
on Sat Jun 26 15:07:18 UTC 2021
Edited
by admin
on Sat Jun 26 15:07:18 UTC 2021
Record UNII
190230I669
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TANDOSPIRONE
INN   MI   WHO-DD  
INN  
Official Name English
TANDOSPIRONE [WHO-DD]
Common Name English
4,7-METHANO-1H-ISOINDOLE-1,3(2H)-DIONE, HEXAHYDRO-2-(4-(4-(2-PYRIMIDINYL)-1-PIPERAZINYL)BUTYL)-, (3A.ALPHA.,4.BETA.,7.BETA.,7A.ALPHA.)-
Common Name English
4,7-METHANO-1H-ISOINDOLE-1,3(2H)-DIONE, HEXAHYDRO-2-(4-(4-(2-PYRIMIDINYL)-1-PIPERAZINYL)BUTYL)-, (3AR,4S,7R,7AS)-REL-
Common Name English
TANDOSPIRONE [INN]
Common Name English
(1R*,2S*,3R*,4S*)-N-(4-(4-(2-PYRIMIDINYL)-1-PIPERAZINYL)BUTYL)-2,3-NORBORNANEDICARBOXIMIDE
Common Name English
TANDOSPIRONE [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C47794
Created by admin on Sat Jun 26 15:07:19 UTC 2021 , Edited by admin on Sat Jun 26 15:07:19 UTC 2021
Code System Code Type Description
DRUG BANK
DB12833
Created by admin on Sat Jun 26 15:07:19 UTC 2021 , Edited by admin on Sat Jun 26 15:07:19 UTC 2021
PRIMARY
ChEMBL
CHEMBL274047
Created by admin on Sat Jun 26 15:07:19 UTC 2021 , Edited by admin on Sat Jun 26 15:07:19 UTC 2021
PRIMARY
EPA CompTox
87760-53-0
Created by admin on Sat Jun 26 15:07:19 UTC 2021 , Edited by admin on Sat Jun 26 15:07:19 UTC 2021
PRIMARY
WIKIPEDIA
Tandospirone
Created by admin on Sat Jun 26 15:07:19 UTC 2021 , Edited by admin on Sat Jun 26 15:07:19 UTC 2021
PRIMARY
MESH
C055267
Created by admin on Sat Jun 26 15:07:19 UTC 2021 , Edited by admin on Sat Jun 26 15:07:19 UTC 2021
PRIMARY
NCI_THESAURUS
C87208
Created by admin on Sat Jun 26 15:07:19 UTC 2021 , Edited by admin on Sat Jun 26 15:07:19 UTC 2021
PRIMARY
INN
6332
Created by admin on Sat Jun 26 15:07:19 UTC 2021 , Edited by admin on Sat Jun 26 15:07:19 UTC 2021
PRIMARY
PUBCHEM
91273
Created by admin on Sat Jun 26 15:07:19 UTC 2021 , Edited by admin on Sat Jun 26 15:07:19 UTC 2021
PRIMARY
DRUG CENTRAL
2563
Created by admin on Sat Jun 26 15:07:19 UTC 2021 , Edited by admin on Sat Jun 26 15:07:19 UTC 2021
PRIMARY
CAS
87760-53-0
Created by admin on Sat Jun 26 15:07:19 UTC 2021 , Edited by admin on Sat Jun 26 15:07:19 UTC 2021
PRIMARY
EVMPD
SUB10829MIG
Created by admin on Sat Jun 26 15:07:19 UTC 2021 , Edited by admin on Sat Jun 26 15:07:19 UTC 2021
PRIMARY
FDA UNII
190230I669
Created by admin on Sat Jun 26 15:07:19 UTC 2021 , Edited by admin on Sat Jun 26 15:07:19 UTC 2021
PRIMARY
MERCK INDEX
M10453
Created by admin on Sat Jun 26 15:07:19 UTC 2021 , Edited by admin on Sat Jun 26 15:07:19 UTC 2021
PRIMARY Merck Index
Related Record Type Details
ACTIVE MOIETY