Seganserin

Seganserin
Clinical data
Other names	R-56413; R56413
Drug class	Serotonin 5-HT2 receptor antagonist; Serotonin 5-HT2A receptor antagonist
ATC code	None;
Pharmacokinetic data
Onset of action	TmaxTooltip Time to peak levels: 1 hour
Elimination half-life	26 hours
Identifiers
	IUPAC name 3-[2-[4-[bis(4-fluorophenyl)methylidene]piperidin-1-yl]ethyl]-2-methylpyrido[1,2-a]pyrimidin-4-one;
CAS Number	87729-89-3;
PubChem CID	71767;
DrugBank	DB19608;
ChemSpider	64806;
UNII	197HL4EZCC;
ChEMBL	ChEMBL1742436;
CompTox Dashboard (EPA)	DTXSID50236594 ;
Chemical and physical data
Formula	C29H27F2N3O
Molar mass	471.552 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1=C(C(=O)N2C=CC=CC2=N1)CCN3CCC(=C(C4=CC=C(C=C4)F)C5=CC=C(C=C5)F)CC3;
	InChI InChI=1S/C29H27F2N3O/c1-20-26(29(35)34-16-3-2-4-27(34)32-20)15-19-33-17-13-23(14-18-33)28(21-5-9-24(30)10-6-21)22-7-11-25(31)12-8-22/h2-12,16H,13-15,17-19H2,1H3; Key:ZGUPMFYFHHSNFK-UHFFFAOYSA-N;

Seganserin (INNTooltip International Nonproprietary Name, BANTooltip British Approved Name; developmental code name R-56413) is a selective serotonin 5-HT₂ receptor antagonist which was studied for the treatment of insomnia and anxiety but was never marketed.^[2]^[3]^[1]^[4]^[5]^[6] It acts as a dual serotonin 5-HT_2A and 5-HT_2C receptor antagonist.^[3]^[4] The drug blocks the head-twitch response induced by serotonin precursor 5-hydroxytryptophan (5-HTP) and the psychedelic drug mescaline in rodents.^[7] It has been found to enhance slow wave sleep (SWS) in clinical studies.^[3]^[4]^[5]^[8]^[1] The drug's time to peak levels is 1 hour and its elimination half-life is 26 hours.^[1] Seganserin reached phase 2 clinical trials prior to the discontinuation of its development.^[2] It was first described in the scientific literature by 1985.^[9]^[10]

References

1 2 3 4 5 Dijk DJ, Beersma DG, Daan S, van den Hoofdakker RH (November 1989). "Effects of seganserin, a 5-HT2 antagonist, and temazepam on human sleep stages and EEG power spectra". European Journal of Pharmacology. 171 (2–3): 207–218. doi:10.1016/0014-2999(89)90109-x. PMID 2576000. Seganserin (R56413, Janssen Pharmaceutica, N.V.) is a highly specific 5HT 2 antagonist devoid of dopaminergic activity (Kennis et al., 1986). The plasma half-life is 26.1 ± 12.9 (S.D.) h. After oral administration maximal plasma levels are reached after 1.0 + 0.5 h (Van de Velde et al., 1986).
1 2 Baxter G, Kennett G, Blaney F, Blackburn T (March 1995). "5-HT2 receptor subtypes: a family re-united?". Trends in Pharmacological Sciences. 16 (3): 105–110. doi:10.1016/s0165-6147(00)88991-9. PMID 7792930.
1 2 3 Monti JM (March 2010). "Serotonin 5-HT(2A) receptor antagonists in the treatment of insomnia: present status and future prospects". Drugs of Today. 46 (3): 183–193. doi:10.1358/dot.2010.46.3.1437247. PMID 20467592.
1 2 3 Landolt HP, Wehrle R (May 2009). "Antagonism of serotonergic 5-HT2A/2C receptors: mutual improvement of sleep, cognition and mood?". The European Journal of Neuroscience. 29 (9): 1795–1809. doi:10.1111/j.1460-9568.2009.06718.x. PMID 19473234.
1 2 Monti JM, Torterolo P, Spence DW, Pandi-Perumal SR (6 November 2017). "Selective Serotonin 5-HT2A Receptor Antagonists and Inverse Agonists Specifically Promote Slow Wave Sleep (Stage N3) in Man". Sleep and Vigilance. 2 (1): 23–31. doi:10.1007/s41782-017-0024-7. ISSN 2510-2265. Retrieved 16 January 2026.
↑ Kennis LE, Vandenberk J, Boey JM, Mertens JC, van Heertum AH, Janssen M, et al. (1986). "The chemical development of selective and specific serotonin S 2 -antagonists". Drug Development Research. 8 (1–4): 133–140. doi:10.1002/ddr.430080116. ISSN 0272-4391. Retrieved 16 January 2026.
↑ Meert TF, Niemegeers CJ, Awouters F, Janssen PA (1988). "Partial and complete blockade of 5-hydroxytrytophan (5-HTP)-induced head twitches in the rat: A study of ritanserin (R 55 667), risperidone (R 64 766), and related compounds". Drug Development Research. 13 (4): 237–244. doi:10.1002/ddr.430130406. ISSN 0272-4391. Retrieved 16 January 2026.
↑ Dijk DJ (June 2010). "Slow-wave sleep deficiency and enhancement: implications for insomnia and its management". The World Journal of Biological Psychiatry. 11 Suppl 1: 22–28. doi:10.3109/15622971003637645. PMID 20509829.
↑ Janssen PA (1985). "Pharmacology of potent and selective S2-serotonergic antagonists". Journal of Cardiovascular Pharmacology. 7 Suppl 7: S2–11. doi:10.1097/00005344-198500077-00002. PMID 2412048.
↑ Critchley MA, Handley SL (1987). "Effects in the X-maze anxiety model of agents acting at 5-HT1 and 5-HT2 receptors". Psychopharmacology. 93 (4): 502–506. doi:10.1007/BF00207243. PMID 3124184.

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[Dijk_1989-1] 1 2 3 4 5 Dijk DJ, Beersma DG, Daan S, van den Hoofdakker RH (November 1989). "Effects of seganserin, a 5-HT2 antagonist, and temazepam on human sleep stages and EEG power spectra". European Journal of Pharmacology. 171 (2–3): 207–218. doi:10.1016/0014-2999(89)90109-x. PMID 2576000. Seganserin (R56413, Janssen Pharmaceutica, N.V.) is a highly specific 5HT 2 antagonist devoid of dopaminergic activity (Kennis et al., 1986). The plasma half-life is 26.1 ± 12.9 (S.D.) h. After oral administration maximal plasma levels are reached after 1.0 + 0.5 h (Van de Velde et al., 1986).

[Baxter_1995-2] 1 2 Baxter G, Kennett G, Blaney F, Blackburn T (March 1995). "5-HT2 receptor subtypes: a family re-united?". Trends in Pharmacological Sciences. 16 (3): 105–110. doi:10.1016/s0165-6147(00)88991-9. PMID 7792930.

[Monti_2010-3] 1 2 3 Monti JM (March 2010). "Serotonin 5-HT(2A) receptor antagonists in the treatment of insomnia: present status and future prospects". Drugs of Today. 46 (3): 183–193. doi:10.1358/dot.2010.46.3.1437247. PMID 20467592.

[Landolt_2009-4] 1 2 3 Landolt HP, Wehrle R (May 2009). "Antagonism of serotonergic 5-HT2A/2C receptors: mutual improvement of sleep, cognition and mood?". The European Journal of Neuroscience. 29 (9): 1795–1809. doi:10.1111/j.1460-9568.2009.06718.x. PMID 19473234.

[Monti_2017-5] 1 2 Monti JM, Torterolo P, Spence DW, Pandi-Perumal SR (6 November 2017). "Selective Serotonin 5-HT2A Receptor Antagonists and Inverse Agonists Specifically Promote Slow Wave Sleep (Stage N3) in Man". Sleep and Vigilance. 2 (1): 23–31. doi:10.1007/s41782-017-0024-7. ISSN 2510-2265. Retrieved 16 January 2026.

[Kennis_1986-6] Kennis LE, Vandenberk J, Boey JM, Mertens JC, van Heertum AH, Janssen M, et al. (1986). "The chemical development of selective and specific serotonin S 2 -antagonists". Drug Development Research. 8 (1–4): 133–140. doi:10.1002/ddr.430080116. ISSN 0272-4391. Retrieved 16 January 2026.

[Meert_1988-7] Meert TF, Niemegeers CJ, Awouters F, Janssen PA (1988). "Partial and complete blockade of 5-hydroxytrytophan (5-HTP)-induced head twitches in the rat: A study of ritanserin (R 55 667), risperidone (R 64 766), and related compounds". Drug Development Research. 13 (4): 237–244. doi:10.1002/ddr.430130406. ISSN 0272-4391. Retrieved 16 January 2026.

[Dijk_2010-8] Dijk DJ (June 2010). "Slow-wave sleep deficiency and enhancement: implications for insomnia and its management". The World Journal of Biological Psychiatry. 11 Suppl 1: 22–28. doi:10.3109/15622971003637645. PMID 20509829.

[Janssen_1985-9] Janssen PA (1985). "Pharmacology of potent and selective S2-serotonergic antagonists". Journal of Cardiovascular Pharmacology. 7 Suppl 7: S2–11. doi:10.1097/00005344-198500077-00002. PMID 2412048.

[Critchley_1987-10] Critchley MA, Handley SL (1987). "Effects in the X-maze anxiety model of agents acting at 5-HT1 and 5-HT2 receptors". Psychopharmacology. 93 (4): 502–506. doi:10.1007/BF00207243. PMID 3124184.

[2]

Seganserin

See also

References