Clinical data | |
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Trade names | Sediel |
Other names | Metanopirone |
AHFS/ Drugs.com | International Drug Names |
Routes of administration | Oral |
ATC code |
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Legal status | |
Legal status |
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Pharmacokinetic data | |
Metabolites | 1-PP |
Elimination half-life | Tandospirone: 2–3 hours 1-PP : 3–5 hours |
Excretion | Urine (70%; 0.1% as unchanged drug) |
Identifiers | |
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CAS Number | |
PubChem CID | |
IUPHAR/BPS | |
ChemSpider | |
UNII | |
ChEBI | |
ChEMBL | |
CompTox Dashboard ( EPA) | |
ECHA InfoCard | 100.210.461 |
Chemical and physical data | |
Formula | C21H29N5O2 |
Molar mass | 383.496 g·mol−1 |
3D model ( JSmol) | |
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(what is this?) (verify) |
Tandospirone, sold under the brand name Sediel, is an anxiolytic and antidepressant medication used in Japan and China, where it is marketed by Dainippon Sumitomo Pharma. It is a member of the azapirone class of drugs and is closely related to other azapirones like buspirone and gepirone.
Tandospirone was introduced for medical use in Japan in 1996 [1] and in China in 2004. [2]
Tandospirone is most commonly used as a treatment for anxiety and depressive disorders, such as generalised anxiety disorder and dysthymia respectively. [3] For both indications it usually takes a couple of weeks for therapeutic effects to begin to be seen, [3] although at higher doses more rapid anxiolytic responses have been seen. [4] It has also been used successfully as a treatment for bruxism. [5]
Tandospirone can be used as an effective augmentation,[ clarification needed] especially when coupled with fluoxetine or clomipramine. [6]
Tandospirone has been tried successfully as an adjunctive treatment for cognitive symptoms[ clarification needed] in schizophrenic individuals. [7]
Common adverse effects include: [3] [1]
Adverse effects with unknown frequency include: [3]
It is not believed to be addictive but is known to produce mild withdrawal effects (e.g., anorexia) after abrupt discontinuation. [3]
Tandospirone acts as a potent and selective 5-HT1A receptor partial agonist, with a Ki affinity value of 27 ± 5 nM [8] and approximately 55 to 85% intrinsic activity. [9] [10] It has relatively weak affinity for the 5-HT2A (1,300 ± 200), 5-HT2C (2,600 ± 60), α1-adrenergic (1,600 ± 80), α2-adrenergic (1,900 ± 400), D1 (41,000 ± 10,000), and D2 (1,700 ± 300) receptors, and is essentially inactive at the 5-HT1B, 5-HT1D, β-adrenergic, and muscarinic acetylcholine receptors, serotonin transporter, and benzodiazepine allosteric site of the GABAA receptor (all of which are > 100,000). [8] There is evidence of tandospirone having low but significant antagonistic activity at the α2-adrenergic receptor through its active metabolite 1-(2-pyrimidinyl)piperazine (1-PP). [11] [12]
The catalytic hydrogenation of cis-5-Norbornene-exo-2,3-dicarboxylic anhydride [129-64-6] (1) gives Norbornane-2exo,3exo-dicarboxylic Acid-anhydride [14166-28-0] (2). Reaction with aqueous ammonia leads to Exo-2,3-norbornanedicarboximide [14805-29-9] (3). Alkylation with 1,4-dibromobutane [110-52-1] (4) gives CID:10661911 (5). Alkylation of the remaining halogen with 2-(1-Piperazinyl)Pyrimidine [20980-22-7] (6) completed the synthesis of Tandospirone (7).
Tandospirone was introduced in Japan for the treatment of anxiety disorders in 1996. [1] It was subsequently also introduced in China in 2004. [2]
Tandospirone is also known as metanopirone and by the developmental code name SM-3997. [20] [21] [22] [5] It is marketed in Japan under the brand name Sediel. [20] [21] [22] [5]
Clinical data | |
---|---|
Trade names | Sediel |
Other names | Metanopirone |
AHFS/ Drugs.com | International Drug Names |
Routes of administration | Oral |
ATC code |
|
Legal status | |
Legal status |
|
Pharmacokinetic data | |
Metabolites | 1-PP |
Elimination half-life | Tandospirone: 2–3 hours 1-PP : 3–5 hours |
Excretion | Urine (70%; 0.1% as unchanged drug) |
Identifiers | |
| |
CAS Number | |
PubChem CID | |
IUPHAR/BPS | |
ChemSpider | |
UNII | |
ChEBI | |
ChEMBL | |
CompTox Dashboard ( EPA) | |
ECHA InfoCard | 100.210.461 |
Chemical and physical data | |
Formula | C21H29N5O2 |
Molar mass | 383.496 g·mol−1 |
3D model ( JSmol) | |
| |
| |
(what is this?) (verify) |
Tandospirone, sold under the brand name Sediel, is an anxiolytic and antidepressant medication used in Japan and China, where it is marketed by Dainippon Sumitomo Pharma. It is a member of the azapirone class of drugs and is closely related to other azapirones like buspirone and gepirone.
Tandospirone was introduced for medical use in Japan in 1996 [1] and in China in 2004. [2]
Tandospirone is most commonly used as a treatment for anxiety and depressive disorders, such as generalised anxiety disorder and dysthymia respectively. [3] For both indications it usually takes a couple of weeks for therapeutic effects to begin to be seen, [3] although at higher doses more rapid anxiolytic responses have been seen. [4] It has also been used successfully as a treatment for bruxism. [5]
Tandospirone can be used as an effective augmentation,[ clarification needed] especially when coupled with fluoxetine or clomipramine. [6]
Tandospirone has been tried successfully as an adjunctive treatment for cognitive symptoms[ clarification needed] in schizophrenic individuals. [7]
Common adverse effects include: [3] [1]
Adverse effects with unknown frequency include: [3]
It is not believed to be addictive but is known to produce mild withdrawal effects (e.g., anorexia) after abrupt discontinuation. [3]
Tandospirone acts as a potent and selective 5-HT1A receptor partial agonist, with a Ki affinity value of 27 ± 5 nM [8] and approximately 55 to 85% intrinsic activity. [9] [10] It has relatively weak affinity for the 5-HT2A (1,300 ± 200), 5-HT2C (2,600 ± 60), α1-adrenergic (1,600 ± 80), α2-adrenergic (1,900 ± 400), D1 (41,000 ± 10,000), and D2 (1,700 ± 300) receptors, and is essentially inactive at the 5-HT1B, 5-HT1D, β-adrenergic, and muscarinic acetylcholine receptors, serotonin transporter, and benzodiazepine allosteric site of the GABAA receptor (all of which are > 100,000). [8] There is evidence of tandospirone having low but significant antagonistic activity at the α2-adrenergic receptor through its active metabolite 1-(2-pyrimidinyl)piperazine (1-PP). [11] [12]
The catalytic hydrogenation of cis-5-Norbornene-exo-2,3-dicarboxylic anhydride [129-64-6] (1) gives Norbornane-2exo,3exo-dicarboxylic Acid-anhydride [14166-28-0] (2). Reaction with aqueous ammonia leads to Exo-2,3-norbornanedicarboximide [14805-29-9] (3). Alkylation with 1,4-dibromobutane [110-52-1] (4) gives CID:10661911 (5). Alkylation of the remaining halogen with 2-(1-Piperazinyl)Pyrimidine [20980-22-7] (6) completed the synthesis of Tandospirone (7).
Tandospirone was introduced in Japan for the treatment of anxiety disorders in 1996. [1] It was subsequently also introduced in China in 2004. [2]
Tandospirone is also known as metanopirone and by the developmental code name SM-3997. [20] [21] [22] [5] It is marketed in Japan under the brand name Sediel. [20] [21] [22] [5]