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
 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

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  3. Donnelly-Roberts, D. L.; Puttfarcken, P. S.; Kuntzweiler, T. A.; Briggs, C. A.; Anderson, D. J.; Campbell, J. E.; Piattoni-Kaplan, M.; McKenna, D. G.; Wasicak, J. T.; Holladay, M. W.; Williams, M.; Arneric, S. P. (1998). "ABT-594 (R)-5-(2-azetidinylmethoxy)-2-chloropyridine: a novel, orally effective analgesic acting via neuronal nicotinic acetylcholine receptors: I. In vitro characterization". The Journal of Pharmacology and Experimental Therapeutics. 285 (2): 777–786. PMID 9580626.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  4. Bannon, A. W.; Decker, M. W.; Curzon, P.; Buckley, M. J.; Kim, D. J.; Radek, R. J.; Lynch, J. K.; Wasicak, J. T.; Lin, N. H.; Arnold, W. H.; Holladay, M. W.; Williams, M.; Arneric, S. P. (1998). "ABT-594 (R)-5-(2-azetidinylmethoxy)-2-chloropyridine: a novel, orally effective antinociceptive agent acting via neuronal nicotinic acetylcholine receptors: II. In vivo characterization". The Journal of Pharmacology and Experimental Therapeutics. 285 (2): 787–794. PMID 9580627.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
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  7. Sorbera LA, Revel L, Leeson PA, Castaner J. ABT-594. Drugs Future 2001; 26: 927-934).
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  15. Lloyd GK, Williams M. Neuronal Nicotinic Acetylcholine Receptors as Novel Drug Targets. Journal of Pharmacology and Experimental Therapeutics. 2000; 292:461-467.
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  19. Jain, K. K. (2004). "Modulators of nicotinic acetylcholine receptors as analgesics". Current opinion in investigational drugs (London, England : 2000). 5 (1): 76–81. PMID 14983978.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>