| Identification | Back Directory | [Name]
TANDOSPIRONE | [CAS]
87760-53-0 | [Synonyms]
Sediel
87760-53-0
TANDOSPIRONE
(3aR,4S,7R,7aS)-rel-
Tandospirone (SM3997)
TANDOSPIRONE USP/EP/BP
Tandospirone [inn:ban]
Tandospirone hydrochloride
3a,4,7,7a-Hexahydro-2-(4-(4-(2-pyrimidinyl)-1-piperazinyl)butyl)-4,7-methano-1H-isoindole-1,3(2H)-dione
(1R*,2S*,3R*,4S*)-N-(4-(4-(2-Pyrimidinyl)-1-piperazinyl)butyl)-2,3-norbornanedicarboximide citrate salt
(3aR,4S,7R,7aS)-2-(4-(4-(pyrimidin-2-yl)piperazin-1-yl)butyl)hexahydro-1H-4,7-methanoisoindole-1,3(2H)-dione
(3αα，4β，7β，7αα)-Hexahydro-2-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-4，7-methano-1H-isoindole-1，3(2H)-dione
rel-(3aR,4S,7R,7aS)-2-(4-(4-(Pyrimidin-2-yl)piperazin-1-yl)butyl)hexahydro-1H-4,7-methanoisoindole-1,3(2H)-dione
4,7-Methano-1H-isoindole-1,3(2H)-dione, hexahydro-2-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-, (3aα,4β,7β,7aα)-
4,7-Methano-1H-isoindole-1,3(2H)-dione, hexahydro-2-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-, (3aa,4b,7b,7aa)-
4,7-Methano-1H-isoindole-1,3(2H)-dione,hexahydro-2-[4-[4-(2-pyriMidinyl)-1-piperazinyl]butyl]-, (3aR,4S,7R,7aS)-rel-
4,7-Methano-1H-isoindole-1,3(2H)-dione, hexahydro-2-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-, (3aR,4S,7R,7aS)-rel- (9CI)
(3aR,4S,7R,7aS)-rel-Hexahydro-2-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-4,7-methano-1H-isoindole-1,3(2H)-dionehydrochloride | [Molecular Formula]
C21H29N5O2 | [MDL Number]
MFCD00209927 | [MOL File]
87760-53-0.mol | [Molecular Weight]
383.49 |
| Chemical Properties | Back Directory | [Melting point ]
112-113.5° | [Boiling point ]
613.9±65.0 °C(Predicted) | [density ]
1.239±0.06 g/cm3(Predicted) | [storage temp. ]
Store at +4°C | [solubility ]
DMSO: soluble38mg/mL | [form ]
Solid | [pka]
7.71±0.10(Predicted) | [color ]
White to Off-White |
| Hazard Information | Back Directory | [Description]
Sediel was launched in Japan as an anxiolytic agent and is a member of the
azapirone family. Ready access to the compound is attained from the ex0 Diels-
Alder adduct of maleic anhydride and cyclopentadiene in a four step convergent
approach. Biochemically, it is a partial agonist of the post-synaptic 5-HT1a receptor.
This metabotropic receptor is coupled to the G proteins and suppresses adenylate
cyclase and phosphatidylinositol metabolism systems. It has low affinity for
dopamine D2, 5-HT2 and α1-adreneric receptors and no affinity for benzodiazepine,
GABA or 5-HT1b binding sites. The primary metabolic product is two orders of
magnitude less active. Tandospirone is as effective as benzodiazepines in anxiolytic
activity but does not have the side-effects (low abuse potential, weak sedative, no
anticonvulsant activity). | [Originator]
Sumitomo (Japan) | [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.
| [Definition]
ChEBI: 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 N-alkylpiperazine, a N-arylpiperazine, a member of pyrimidines, a bridged compound and a dicarboximide. It is a conjugate base of a tandospirone(1+). | [Preparation]
Tandospirone is attained from the exo diels-alder adduct of maleic anhydride and cyclopentadiene in a four step convergent approach. | [Brand name]
Sediel | [Biological Activity]
5-HT 1A receptor partial agonist (K i = 27 nM) that displays selectivity over 5-HT 2 , 5-HT 1C , α 1 , α 2 , D 1 and D 2 receptors (K i values ranging from 1300-41000 nM). Inactive at 5-HT uptake sites, 5-HT 1B , β -adrenergic, muscarinic and benzodiazepine receptors. Displays anxiolytic activity. | [References]
[1] shimizu h1, hirose a, tatsuno t, nakamura m, katsube j. pharmacological properties of sm-3997: a new anxioselective anxiolytic candidate. jpn j pharmacol. 1987 dec; 45(4):493-500. |
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