Tetracyclic antidepressant
Tetracyclic antidepressants (TeCAs) are a class of antidepressants that were first introduced in the 1970s. They are named after their tetracyclic chemical structure, containing four rings of atoms, and are closely related to the tricyclic antidepressants (TCAs), which contain three rings of atoms.
List of TeCAs
Marketed
- secondary amines
- Mianserin (Tolvon)
- Mirtazapine (Remeron)
- Setiptiline (Tecipul)
Drugs that contain four rings not all fused together but are sometimes still classified as TeCAs include:
- Amoxapine (Asendin) – often classified as a TCA and grouped with the secondary amines
- Quetiapine (Seroquel) - an atypical antipsychotic sometimes used as an adjunct antidepressant
Miscellaneous
- Benzoctamine (Tacitin) – a tetracyclic compound and is closely related 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
- Loxapine (Adasuve, Loxitane) – a typical antipsychotic that produces amoxapine as a major metabolite and is said to have antidepressant effects, but it is not usually regarded as a TeCA
Drugs that contain four rings not all fused together but could still be classified as tetracyclic include:
- appetite suppressantand with potential antidepressant effects, but not classified as a TeCA
Never marketed
- Aptazapine (CGS-7525A) – a close analogue of mirtazapine
- Esmirtazapine (ORG-50,081) – the (S)-(+) enantiomer of mirtazapine
- Oxaprotiline (C 49-802 BDA) – a close analogue of maprotiline
Drugs that contain four rings not all fused together but could still be classified as tetracyclic include:
- Ciclazindol (WY-23,409) – a close analogue of mazindol
Pharmacology
TeCAs have diverse
Binding profiles
The binding profiles of various TeCAs in terms of their
Compound | SERT | NET | DAT | 5-HT1A | 5-HT2A | 5-HT2B | 5-HT2C | 5-HT3 | 5-HT6 | 5-HT7 | α1 | α2 | D2 |
H1 |
H2 |
mACh |
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Amoxapine | 58 | 16 | 4,310 | ND | 0.5 | ND | 2.0 | ND | 6.0–50 | 41 | 50 | 2,600 | 3.6–160 | 7.9–25 | ND | 1,000 |
Maprotiline | 5,800 | 11–12 | 1,000 | ND | 51 | ND | 122 | ND | ND | 50 | 90 | 9,400 | 350–665 | 0.79–2.0 | 776 | 570 |
Mianserin | 4,000 | 71 | 9,400 | 400–2,600 | 1.6–20 | 1.6–55 | 0.63–6.5 | 5.8–300 | 55–81 | 48–56 | 34 | 3.8–73 | ≥2,100 | 0.30–1.7 | 437 | 820 |
Mirtazapine | >10,000 | ≥4,600 | >10,000 | ≥3,330 | 6.3–69 | 200 | 8.9–39 | 7.9 | ND | 265 | 316–1,815 | 18–88 | >5,454 | 0.14–1.6 | >10,000 | 670 |
Setiptiline | >10,000 | 220 | >10,000 | ND | ND | ND | ND | ND | ND | ND | ND | 24 | ND | ND | ND | ND |
Values are Ki (nM). The smaller the value, the more strongly the drug binds to the site. For assay species and references, see the individual drug articles. Most but not all values are for human proteins. |
The TeCAs act as
inhibitors
of the transporters.
See also
References
- ISSN 0300-7995.
- S2CID 28546654.
- ^ Roth, BL; Driscol, J. "PDSP Ki Database". Psychoactive Drug Screening Program (PDSP). University of North Carolina at Chapel Hill and the United States National Institute of Mental Health. Retrieved 14 August 2017.