Tandospirone

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Tandospirone
File:Tandospirone.svg
Systematic (IUPAC) name
(1R,2R,6S,7S)-4-{4-[4-(pyrimidin-2-yl)piperazin-1-yl]butyl}-4-azatricyclo[5.2.1.02,6]decane-3,5-dione
Clinical data
Routes of
administration		 Oral
Legal status
Legal status
  • ℞ (Prescription only)
Pharmacokinetic data
Biological half-life 1.2–1.4 hours
Identifiers
CAS Number 112457-95-1
ATC code none
PubChem CID 91273
IUPHAR/BPS 55
Chemical data
Formula C21H29N5O2
Molar mass 383.487 g/mol[[Script error: No such module "String".]]
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Tandospirone (Sediel), also known as metanopirone, is an anxiolytic and antidepressant used in China and Japan, where it is marketed by Dainippon Sumitomo Pharma. It is a member of the azapirone and piperazine chemical classes and is closely related to other agents like buspirone and gepirone.

Pharmacology

Tandospirone acts as a potent and selective 5-HT1A receptor partial agonist, with a Ki affinity value of 27 ± 5 nM[1] and approximately 55-85% intrinsic activity.[2][3] It has weak but clinically negligible 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 (SERT), and benzodiazepine (BDZ) allosteric site of the GABAA receptor (all of which are > 100,000).[1] 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), however.[4][5]

Dosage

Tandospirone is typically used at a dose of 30 mg/daily[6] taken in divided doses of 10 mg three times per day due to its short half-life. Though originally considered a relatively weak anxiolytic agent,[6] a clinical study found that doubling the dose to 60 mg/daily resulted in a "remarkable anxiolytic effect with an early onset of action, and without significant adverse effects", as well as "excellent anxiolytic efficacy that is comparable to that of the benzodiazepines".[6] [7]

Side effects

Side effects of tandospirone and other 5-HT1A partial agonists are relatively mild and may include nausea, diarrhea, headache, dizziness, and restlessness.[8]

Chemistry

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Yevich, Joseph P.; New, James S.; Smith, David W.; Lobeck, Walter G.; Catt, John D.; Minielli, Joseph L.; Eison, Michael S.; Taylor, Duncan P.; Riblet, Leslie A. (1986). "Synthesis and biological evaluation of 1-(1,2-benzisothiazol-3-yl)- and (1,2-benzisoxazol-3-yl)piperazine derivatives as potential antipsychotic agents". Journal of Medicinal Chemistry. 29 (3): 359. doi:10.1021/jm00153a010. PMID 2869146. 

See also

References

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GABAA PAMs
Others
α2δ VDCC Blockers
5-HT1A Agonists
Azapirones: Buspirone • Gepirone • Tandospirone; Others: Flesinoxan • Oxaflozane
H1 Antagonists
Diphenylmethanes: Captodiame • Hydroxyzine; Others: Brompheniramine • Chlorpheniramine • Pheniramine
CRH1 Antagonists
NK2 Antagonists
MCH1 antagonists
mGluR2/3 Agonists
mGluR5 NAMs
TSPO agonists
σ1 agonists
Others

M: PSO/PSI

dsrd (o, p, m, p, a, d, s), sysi/epon, spvo

proc, drug(N5A/5B/5C/6A/6B/6D)

ja:タンドスピロン
  1. ↑ 1.0 1.1 Hamik; Oksenberg, D; Fischette, C; Peroutka, SJ (1990). "Analysis of tandospirone (SM-3997) interactions with neurotransmitter receptor binding sites". Biological psychiatry. 28 (2): 99–109. doi:10.1016/0006-3223(90)90627-E. PMID 1974152. 
  2. ↑ Tanaka; Tatsuno, T; Shimizu, H; Hirose, A; Kumasaka, Y; Nakamura, M (1995). "Effects of tandospirone on second messenger systems and neurotransmitter release in the rat brain". General pharmacology. 26 (8): 1765–72. doi:10.1016/0306-3623(95)00077-1. PMID 8745167. 
  3. ↑ Yabuuchi, Kazuki; Tagashira, Rie; Ohno, Yukihiro (2004). "Effects of tandospirone, a novel anxiolytic agent, on human 5-HT1A receptors expressed in Chinese hamster ovary cells (CHO cells)". Biogenic Amines. 18: 319. doi:10.1163/1569391041501933. 
  4. ↑ Blier; Curet, O; Chaput, Y; De Montigny, C (1991). "Tandospirone and its metabolite, 1-(2-pyrimidinyl)-piperazine--II. Effects of acute administration of 1-PP and long-term administration of tandospirone on noradrenergic neurotransmission". Neuropharmacology. 30 (7): 691–701. doi:10.1016/0028-3908(91)90176-C. PMID 1681447. 
  5. ↑ Miller; Thompson, ML; Byrnes, JJ; Greenblatt, DJ; Shemer, A (1992). "Kinetics, brain uptake, and receptor binding of tandospirone and its metabolite 1-(2-pyrimidinyl)-piperazine". Journal of clinical psychopharmacology. 12 (5): 341–5. PMID 1362206. 
  6. ↑ 6.0 6.1 6.2 Nishitsuji; To, H; Murakami, Y; Kodama, K; Kobayashi, D; Yamada, T; Kubo, C; Mine, K (2004). "Tandospirone in the treatment of generalised anxiety disorder and mixed anxiety-depression : results of a comparatively high dosage trial". Clinical drug investigation. 24 (2): 121–6. PMID 17516698. 
  7. ↑ Evans; Troisi Jr, 2nd; Griffiths, RR (1994). "Tandospirone and alprazolam: comparison of behavioral effects and abuse liability in humans". The Journal of pharmacology and experimental therapeutics. 271 (2): 683–94. PMID 7965783. 
  8. ↑ Feighner JP, Boyer WF (1989). "Serotonin-1A anxiolytics: an overview". Psychopathology. 22 Suppl 1: 21–6. PMID 2567039. 
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