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Seganserin

From Wikipedia, the free encyclopedia

Pharmaceutical compound
Seganserin
Clinical data
Other namesR-56413; R56413
Drug classSerotonin5-HT2 receptorantagonist;Serotonin 5-HT2A receptor antagonist
ATC code
  • None
Pharmacokinetic data
Onset of actionTmaxTooltip Time to peak levels: 1 hour[1]
Eliminationhalf-life26 hours[1]
Identifiers
  • 3-[2-[4-[bis(4-fluorophenyl)methylidene]piperidin-1-yl]ethyl]-2-methylpyrido[1,2-a]pyrimidin-4-one
CAS Number
PubChemCID
DrugBank
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC29H27F2N3O
Molar mass471.552 g·mol−1
3D model (JSmol)
  • CC1=C(C(=O)N2C=CC=CC2=N1)CCN3CCC(=C(C4=CC=C(C=C4)F)C5=CC=C(C=C5)F)CC3
  • 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 nameR-56413) is aselectiveserotonin5-HT2 receptorantagonist which was studied for the treatment ofinsomnia andanxiety but was never marketed.[2][3][1][4][5][6] It acts as a dual serotonin5-HT2A and5-HT2C receptor antagonist.[3][4] The drug blocks thehead-twitch response induced byserotonin precursor5-hydroxytryptophan (5-HTP) and thepsychedelic drugmescaline in rodents.[7] It has been found to enhanceslow wave sleep (SWS) inclinical studies.[3][4][5][8][1] The drug'stime to peak levels is 1 hour and itselimination half-life is 26 hours.[1] Seganserin reachedphase 2clinical trials prior to the discontinuation of its development.[2] It was first described in thescientific literature by 1985.[9][10]

See also

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References

[edit]
  1. ^abcdeDijk 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).
  2. ^abBaxter 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.
  3. ^abcMonti 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.
  4. ^abcLandolt 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.
  5. ^abMonti 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. Retrieved16 January 2026.
  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. Retrieved16 January 2026.
  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. Retrieved16 January 2026.
  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.
  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.
  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.
5-HT1
5-HT1A
5-HT1B
5-HT1D
5-HT1E
5-HT1F
5-HT2
5-HT2A
5-HT2B
5-HT2C
5-HT37
5-HT3
5-HT4
5-HT5A
5-HT6
5-HT7
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