TANDOSPIRONE CITRATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H29N5O2.C6H8O7
Molecular Weight	575.6108
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)CC(O)(CC(O)=O)C(O)=O.[H][C@@]12[C@H]3CC[C@H](C3)[C@]1([H])C(=O)N(CCCCN4CCN(CC4)C5=NC=CC=N5)C2=O

InChI

InChIKey=DMLGUJHNIWGCKM-DPFKZJTMSA-N

InChI=1S/C21H29N5O2.C6H8O7/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;7-3(8)1-6(13,5(11)12)2-4(9)10/h3,6-7,15-18H,1-2,4-5,8-14H2;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/t15-,16+,17+,18-;

HIDE SMILES / InChI

Description
Sources: http://www.ds-pharma.com/release/sumitomo/2004/20040224.html
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serotonin 1a (5-HT1a) receptor 172 Target ID: CHEMBL214 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1974152	Partial Agonist 290		27.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Generalized anxiety disorder 32 Sources: http://www.ds-pharma.com/release/sumitomo/2004/20040224.html	Primary		Approved 8429	Sediel Approved Use Unknown Launch Date 2003
Schizophrenia 298 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11579010	Primary		Phase IV 63	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Agonist and antagonist actions of antipsychotic agents at 5-HT1A receptors: a [35S]GTPgammaS binding study.	1998 Aug 21	9760039

Patents

Sample Use Guides

In Vivo Use Guide

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.

Name

Type

Language

TANDOSPIRONE CITRATE

Official Name

English

TANDOSPIRONE CITRATE [USAN]

Common Name

English

Tandospirone citrate [WHO-DD]

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-, 2-HYDROXY-1,2,3-PROPANETRICARBOXYLATE (1:1)

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.)-, 2-HYDROXY-1,2,3-PROPANETRICARBOXYLATE

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.)-, 2-HYDROXY-1,2,3-PROPANETRICARBOXYLATE (1:1)

Common Name

English

(1R*,2S*,3R*,4S*)-N-(4-(4-(2-PYRIMIDINYL)-1-PIPERAZINYL)BUTYL)-2,3-NORBORNANEDICARBOXIMIDE CITRATE (1:1)

Common Name

English

SEDIEL

Brand Name

English

TANDOSPIRONE CITRATE [MI]

Common Name

English

TANDOSPIRONE CITRATE [JAN]

Common Name

English

SM-3997

Code

English

TANDOSPIRONE CITRATE [MART.]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C28197