Tebanicline

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Tebanicline
Tebaniciclina.png
Systematic (IUPAC) name
5-([(2R)-Azetidin-2-yl]methoxy)-2-chloropyridine
Identifiers
CAS Number 198283-73-7 YesY
ATC code none
PubChem CID: 3075702
IUPHAR/BPS 3989
ChemSpider 2334347 N
UNII 9KX8NKV538 YesY
ChEMBL CHEMBL430497 N
Chemical data
Formula C9H11ClN2O
Molecular mass 198.649
  • C1CN[C@H]1COC2=CN=C(C=C2)Cl
  • InChI=1S/C9H11ClN2O/c10-9-2-1-8(5-12-9)13-6-7-3-4-11-7/h1-2,5,7,11H,3-4,6H2/t7-/m1/s1 N
  • Key:MKTAGSRKQIGEBH-SSDOTTSWSA-N N
 NYesY (what is this?)  (verify)

Tebanicline (Ebanicline, ABT-594) is a potent synthetic nicotinic (non-opioid) analgesic drug developed by Abbott. It was developed as a less toxic analogue of the potent poison dart frog-derived compound epibatidine, which is some 200x stronger than morphine as an analgesic but produces extremely dangerous toxic side effects.[1][2] Like epibatidine, tebanicline showed potent analgesic activity against neuropathic pain in both animal and human trials, but with far less toxicity than its parent compound.[3][4][5][6][7][8]

Tebanicline got as far as Phase II trials in humans,[9] but was dropped from further development due to unacceptable incidence of gastrointestinal side effects.[10] However further research in this area is ongoing,[11][12][13][14] and it is expected that development of new neural nicotinic acetylcholine receptor agonists will be likely to lead to novel analgesics suitable for use in humans within the next few years.[15][16][17][18]

It acts as a partial agonist at neuronal nicotinic acetylcholine receptors, binding to both the α3β4 and the α4β2 subtypes.[19]

References

  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ Sorbera LA, Revel L, Leeson PA, Castaner J. ABT-594. Drugs Future 2001; 26: 927-934).
  8. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  9. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  10. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  11. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  12. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  13. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  14. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  15. ↑ Lloyd GK, Williams M. Neuronal Nicotinic Acetylcholine Receptors as Novel Drug Targets. Journal of Pharmacology and Experimental Therapeutics. 2000; 292:461-467.
  16. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  17. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  18. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  19. ↑ Lua error in package.lua at line 80: module 'strict' not found.


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