Tetracyclic antidepressant

Chemical structure of the tetracyclic antidepressant mirtazapine. Notice its four fused rings.

Tetracyclic antidepressants (TeCAs) are a class of drugs used primarily as antidepressants that were first introduced in the 1970s. They are named after their chemical structure which contains four rings of atoms and are closely related to the tricyclic antidepressants (TCAs) which contain three rings of atoms.

List of TeCAs

The TeCAs include the following agents:

• Pharmaceutical drugs
  • Amoxapine (Asendin) — sometimes classed as a secondary amine tricyclic antidepressant; active metabolite of the typical antipsychotic, loxapine.
  • Maprotiline (Deprilept, Ludiomil, Psymion)
  • Mazindol (Mazanor, Sanorex)
  • Mianserin (Bolvidon, Norval, Tolvon)
  • Mirtazapine (Remeron, Avanza, Zispin)
  • Setiptiline (Tecipul)
  • Trazodone (Desyrel)
• Research chemicals
  • Aptazapine (CGS-7525A)
  • Ciclazindol (WY-23,409)
  • Esmirtazapine (ORG-50,081)
  • Oxaprotiline
  • Vabicaserin (SCA-136) is a selective 5-HT_2C full agonist that was being investigated as an antidepressant and atypical antipsychotic and was later dropped by its developer, Wyeth.

Pharmacology

Binding profiles

The affinities (K_d (nM)) of a selection of TeCAs have been compared below at an assortment of binding sites:^{[1][2][3][4][5][6][7][8][9]}

The selected ligands act as antagonists (or inverse agonists depending on the site in question) at all receptors listed and as inhibitors of all transporters listed.

See also

• Tricyclic antidepressant (TCA)

References

1. ↑ Brunton, Laurence (2011). Goodman & Gilman's The Pharmacological Basis of Therapeutics 12th Edition. China: McGraw-Hill. pp. 406–410. ISBN 978-0-07-162442-8. 
2. ↑ Tatsumi M, Groshan K, Blakely RD, Richelson E (December 1997). "Pharmacological profile of antidepressants and related compounds at human monoamine transporters". European Journal of Pharmacology 340 (2–3): 249–58. doi:10.1016/S0014-2999(97)01393-9. PMID 9537821. 
3. ↑ Wander TJ, Nelson A, Okazaki H, Richelson E (December 1986). "Antagonism by antidepressants of serotonin S1 and S2 receptors of normal human brain in vitro". European Journal of Pharmacology 132 (2–3): 115–21. doi:10.1016/0014-2999(86)90596-0. PMID 3816971. 
4. ↑ Richelson E, Nelson A (July 1984). "Antagonism by antidepressants of neurotransmitter receptors of normal human brain in vitro". The Journal of Pharmacology and Experimental Therapeutics 230 (1): 94–102. PMID 6086881. 
5. ↑ Tatsumi M, Jansen K, Blakely RD, Richelson E (March 1999). "Pharmacological profile of neuroleptics at human monoamine transporters". European Journal of Pharmacology 368 (2–3): 277–83. doi:10.1016/S0014-2999(99)00005-9. PMID 10193665. 
6. ↑ Wander TJ, Nelson A, Okazaki H, Richelson E (November 1987). "Antagonism by neuroleptics of serotonin 5-HT1A and 5-HT2 receptors of normal human brain in vitro". European Journal of Pharmacology 143 (2): 279–82. doi:10.1016/0014-2999(87)90544-9. PMID 2891550. 
7. ↑ Richelson E, Nelson A (August 1984). "Antagonism by neuroleptics of neurotransmitter receptors of normal human brain in vitro". European Journal of Pharmacology 103 (3–4): 197–204. doi:10.1016/0014-2999(84)90478-3. PMID 6149136. 
8. ↑ Fernández J, Alonso JM, Andrés JI, et al. (March 2005). "Discovery of new tetracyclic tetrahydrofuran derivatives as potential broad-spectrum psychotropic agents". Journal of Medicinal Chemistry 48 (6): 1709–12. doi:10.1021/jm049632c. PMID 15771415. 
9. ↑ de Boer TH, Maura G, Raiteri M, de Vos CJ, Wieringa J, Pinder RM (April 1988). "Neurochemical and autonomic pharmacological profiles of the 6-aza-analogue of mianserin, Org 3770 and its enantiomers". Neuropharmacology 27 (4): 399–408. doi:10.1016/0028-3908(88)90149-9. PMID 3419539.