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Pelanserin

From Wikipedia, the free encyclopedia

Pharmaceutical compound
Pelanserin
Clinical data
Other namesTR2515; TR-2515
Routes of
administration
Oral[1]
Drug classSerotonin 5-HT2A receptor antagonist;α1-Adrenergic receptor antagonist
ATC code
  • None
Pharmacokinetic data
Onset of action<1 hour (TmaxTooltip time to peak levels)[1]
Eliminationhalf-life3.8 hours[1]
Identifiers
  • 3-[3-(4-phenylpiperazin-1-yl)propyl]quinazoline-2,4(1H,3H)-dione
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC21H24N4O2
Molar mass364.449 g·mol−1
3D model (JSmol)
  • C1CN(CCN1CCCN2C(=O)C3=CC=CC=C3NC2=O)C4=CC=CC=C4
  • InChI=1S/C21H24N4O2/c26-20-18-9-4-5-10-19(18)22-21(27)25(20)12-6-11-23-13-15-24(16-14-23)17-7-2-1-3-8-17/h1-5,7-10H,6,11-16H2,(H,22,27)
  • Key:WPKPLSFHHBBLRY-UHFFFAOYSA-N

Pelanserin (developmental code nameTR-2515) is aserotonin5-HT2 andα1-adrenergic receptorantagonist which was under development for the treatment ofhypertension but was never marketed.[2][3] Its development was discontinued in 2001.[2]

Pharmacology

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Pharmacokinetics

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Thepharmacokinetics of pelanserin have been studied.[4] It has a relatively shortelimination half-life.[5][4] The drug'stime to peak levels was less than 1 hour and its half-life was 3.8 hours in a single subject in ananalytical study.[1]

Chemistry

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Synthesis

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Synthesis of pelanserin

Pelanserin (3) can besynthesized by a reaction betweenisatoic anhydride (1) and 1-(3-aminopropyl)-4-phenylpiperazine (2) in the presence ofphosgene.[6][7][8][9][10][11][12][13]

See also

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References

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  1. ^abcdFlores-Murrieta FJ, Hong E, Castañeda-Hernández G (June 1988). "Sensitive high-performance liquid chromatographic assay of pelanserin, a novel antihypertensive agent, in plasma samples".Journal of Chromatography.428 (1):167–172.doi:10.1016/s0378-4347(00)83903-1.PMID 3170670.
  2. ^ab"Pelanserin".AdisInsight. 30 August 2002. Retrieved17 January 2026.
  3. ^Villalobos-Molina R, Ibarra M, Hong E (April 1995). "The 5-HT2 receptor antagonist, pelanserin, inhibits alpha 1-adrenoceptor-mediated vasoconstriction in vitro".European Journal of Pharmacology.277 (2–3):181–185.doi:10.1016/0014-2999(95)00074-u.PMID 7493607.
  4. ^abFlores-Murrieta FJ, Herrera JE, Castañeda-Hernández G, Hong E (1992). "Pharmacokinetics of pelanserin in healthy volunteers".Proceedings of the Western Pharmacology Society.35:113–116.PMID 1502209.
  5. ^Espinoza R, Hong E, Villafuerte L (May 2000). "Influence of admixed citric acid on the release profile of pelanserin hydrochloride from HPMC matrix tablets".International Journal of Pharmaceutics.201 (2):165–173.doi:10.1016/s0378-5173(00)00406-3.PMID 10878323.Pelanserin is a weakly basic experimental drug with a short half-life and a prolonged release formulation was developed using hydroxypropyl methylcellulose (HPMC) and citric acid to set up a system bringing about gradual release of this drug.
  6. ^Hayao S, Havera HJ, Strycker WG, Leipzig TJ, Kulp RA, Hartzler HE (November 1965). "New sedative and hypotensive 3-substituted 2,4(1H,3H)-quinazolinediones".Journal of Medicinal Chemistry.8 (6):807–815.doi:10.1021/jm00330a017.PMID 5885076.
  7. ^Havera HJ, Vidrio H (December 1979). "Derivatives of 1,3-disubstituted 2,4(1H,3H)-quinazolinediones as possible peripheral vasodilators or antihypertensive agents".Journal of Medicinal Chemistry.22 (12):1548–1550.doi:10.1021/jm00198a024.PMID 231656.
  8. ^Garcia JD, Somanathan R, Rivero IA, Aguirre G, Hellberg LH (2000). "Synthesis of Deuterium-Labeled Antihypertensive 3-(4-Phenyl-1′-Piperazinyl)-Propyl-2,4-Quinazolinedione".Synthetic Communications.30 (15):2707–2711.doi:10.1080/00397910008086895.
  9. ^Li X, Lee YR, Kim SH (2011). "Concise Synthesis of Pelanserine, Goshuyuamide II, and Wuchuyuamide II with Quinazolinedione Nuclei".Bulletin of the Korean Chemical Society.32 (9):3480–3482.doi:10.5012/bkcs.2011.32.9.3480.
  10. ^Cortez R, Rivero IA, Somanathan R, Aguirre G, Ramirez F, Hong E (1991). "Synthesis of Quinazolinedione Using Triphosgene".Synthetic Communications.21 (2):285–292.doi:10.1080/00397919108020823.
  11. ^AT 269143B, "Verfahren zur Herstellung von neuen Chinazolindionderivaten und ihrer Säureadditionssalze bzw. ihrer entsprechenden Piperaziniumverbindungen [Process for the preparation of new quinazolinedione derivatives and their acid addition salts or their corresponding piperazinium compounds]", published 1969-03-10, assigned to Miles Laboratories, Inc. 
  12. ^US 3274194, Shin H, "Quinazolinedione derivatives", issued 20 September 1966, assigned to Bayer Corp. 
  13. ^US 3919425, Vidrio H, "Method of producing vasodilation using certain 3-substituted-quinazoline derivatives", issued 11 November 1975, assigned to Bayer Corp. 
α1
Agonists
Antagonists
α2
Agonists
Antagonists
β
Agonists
Antagonists
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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