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Pelanserin

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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]
Elimination half-life3.8 hours[1]
Identifiers
  • 3-[3-(4-phenylpiperazin-1-yl)propyl]quinazoline-2,4(1H,3H)-dione
CAS Number
PubChem CID
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 name TR-2515) is a serotonin 5-HT2 and α1-adrenergic receptor antagonist which was under development for the treatment of hypertension but was never marketed.[2][3] Its development was discontinued in 2001.[2]

Pharmacology

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Pharmacokinetics

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The pharmacokinetics of pelanserin have been studied.[4] It has a relatively short elimination half-life.[5][4] The drug's time to peak levels was less than 1 hour and its half-life was 3.8 hours in a single subject in an analytical study.[1]

Chemistry

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Synthesis

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Synthesis of pelanserin

Pelanserin (3) can be synthesized by a reaction between isatoic anhydride (1) and 1-(3-aminopropyl)-4-phenylpiperazine (2) in the presence of phosgene.[6][7][8][9][10][11][12][13]

See also

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References

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  1. 1 2 3 4 Flores-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. 1 2 "Pelanserin". AdisInsight. 30 August 2002. Retrieved 17 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. 1 2 Flores-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.
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