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Tetracyclic antidepressants (TeCAs) are a class of 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:

• Marketed
  • Maprotiline (Deprilept, Ludiomil, Psymion)
  • Mianserin (Bolvidon, Norval, Tolvon)
  • Mirtazapine (Remeron, Avanza, Zispin)
  • Setiptiline (Tecipul)
• Never marketed
  • Aptazapine (CGS-7525A)
  • Esmirtazapine (ORG-50,081)
  • Oxaprotiline (C 49-802 BDA)

Drugs which contain four rings but not fused together that are sometimes classified as TeCAs include:

• Marketed
  • Amoxapine (Asendin) — often classified as a secondary amine tricyclic antidepressant
  • Loxapine (Loxapac, Loxitane, Adasuve) — a tricyclic antipsychotic with antidepressant properties; produces amoxapine as an active metabolite
  • Mazindol (Mazanor, Sanorex)
• Never marketed
  • Ciclazindol (WY-23,409)

Benzoctamine (Tacitin) is closely related to the TeCAs and particularly to maprotiline, with the two compounds differing only in the length of their side chain, but benzoctamine is not used as an antidepressant and is instead used as an anxiolytic.

Pharmacology

Binding profiles

The affinities (K_d (nM)) of a selection of TeCAs have been compared below at an assortment of binding sites:

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

• Noradrenergic and specific serotonergic antidepressant

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): 249–258. 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): 115–121. 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): 277–283. 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): 279–282. 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.

• Chemical classes of psychoactive drugs
• Tetracyclic antidepressants