Pelanserin

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]

Other namesTR2515; TR-2515

Routes of
administrationOral^[1]

Drug classSerotonin 5-HT_2A receptor antagonist; α₁-Adrenergic receptor antagonist

ATC code

None

Quick facts Clinical data, Other names ...

Pelanserin
Clinical data

Other names	TR2515; TR-2515
Routes of administration	Oral^[1]
Drug class	Serotonin 5-HT_2A receptor antagonist; α₁-Adrenergic receptor antagonist
ATC code	None
Pharmacokinetic data
Onset of action	<1 hour (T_maxTooltip time to peak levels)^[1]
Elimination half-life	3.8 hours^[1]
Identifiers
IUPAC name 3-[3-(4-phenylpiperazin-1-yl)propyl]quinazoline-2,4(1H,3H)-dione
CAS Number	2208-51-7^Y
PubChem CID	65435
ChemSpider	58898
UNII	6SNR96E409
CompTox Dashboard (EPA)	DTXSID60176578
Chemical and physical data
Formula	C₂₁H₂₄N₄O₂
Molar mass	364.449 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C1CN(CCN1CCCN2C(=O)C3=CC=CC=C3NC2=O)C4=CC=CC=C4
InChI 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

Pharmacology

Pharmacokinetics

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

Synthesis

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]

References

[1]
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]
"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]
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.