Tandospirone

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Tandospirone
Clinical data
Trade namesSediel
Other namesMetanopirone
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • In general: ℞ (Prescription only)
1-PPTooltip 1-(2-Pyrimidinyl)piperazine: 3–5 hours
ExcretionUrine (70%; 0.1% as unchanged drug)
Identifiers
  • (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
JSmol)
  • O=C1N(C(=O)[C@H]3[C@@H]1[C@@H]2CC[C@H]3C2)CCCCN5CCN(c4ncccn4)CC5
  • 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- checkY
  • Key:CEIJFEGBUDEYSX-FZDBZEDMSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Tandospirone, sold under the brand name Sediel, is an

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]

Medical uses

Anxiety and depression

Tandospirone is most commonly used as a treatment for

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]

Augmentation for depression

Tandospirone can be used as an effective augmentation,[clarification needed] especially when coupled with fluoxetine or clomipramine.[6]

Other uses

Tandospirone has been tried successfully as an adjunctive treatment for cognitive symptoms[clarification needed] in schizophrenic individuals.[7]

Side effects

Common adverse effects include:[3][1]

  • Dizziness
  • Drowsiness
  • Insomnia
  • Headache
  • Gastrointestinal disorders
  • Dry mouth
  • Negative influence on explicit memory function[3]
  • Nausea[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]

Pharmacology

Pharmacodynamics

Tandospirone acts as a

1-(2-pyrimidinyl)piperazine (1-PP).[11][12]

Chemistry

Synthesis
Radiolabelled:[18] Mannich reaction method:[19]

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).

History

Tandospirone was introduced in Japan for the treatment of anxiety disorders in 1996.[1] It was subsequently also introduced in China in 2004.[2]

Society and culture

Name

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]

References

  1. ^
    ISBN 978-3-0348-8470-9
    . Retrieved 2023-10-07.
  2. ^
    ISBN 978-3-030-62059-2
    . Retrieved 2023-10-07.
  3. ^
    doi:10.2165/00023210-199605020-00006
    .
  4. S2CID 38339009
    .
  5. ^ a b c "Tandospirone". Martindale: The Complete Drug Reference. The Royal Pharmaceutical Society of Great Britain. 23 September 2011. Retrieved 14 November 2013.
  6. PMID 29254282
    .
  7. PMID 11579010
    .
  8. ^
    S2CID 25608914
    .
  9. PMID 8745167
    .
  10. doi:10.1163/1569391041501933
    .
  11. S2CID 44297577
    .
  12. S2CID 22449352
    .
  13. PMID 1687114
    .
  14. S2CID 83676454
    .
  15. doi:10.1358/dof.1986.011.11.53048
    .
  16. ^ EP 0082402, Ishizumi K, Antoku F, Asami Y, published 1986, assigned to Sumitomo Chemical Company, Limited) 
  17. ^ CN 101880274A, Zhang J, Li L, published 2010, assigned to PKUCare Southwest Synthetic Pharmaceutical Corp., Ltd. 
  18. ISSN 0362-4803
    .
  19. ^ WO 2012016569, Hansen JB, Thomsen MS, assigned to Conrig Pharma ApS 
  20. ^
    ISBN 978-1-4757-2085-3
    . Retrieved 2023-10-07.
  21. ^
    ISBN 978-3-88763-101-7
    . Retrieved 2023-10-07.
  22. ^
    ISBN 978-94-011-4439-1
    . Retrieved 2023-10-07.
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