PNU-142633

PNU-142633
Names
	Preferred IUPAC name (1S)-1-{2-[4-(4-Carbamoylphenyl)piperazin-1-yl]ethyl}-N-methyl-3,4-dihydro-1H-2-benzopyran-6-carboxamide
	Other names PNU-142633F
Identifiers
CAS Number	187665-65-2 ; 249765-69-3 (maleate) ;
3D model (JSmol)	Interactive image;
ChemSpider	8020862;
PubChem CID	9845148;
UNII	B54P1BQ73L ; VF98F3655P (maleate) ;
CompTox Dashboard (EPA)	DTXSID00431734 ;
	InChI InChI=1S/C24H30N4O3/c1-26-24(30)19-4-7-21-18(16-19)9-15-31-22(21)8-10-27-11-13-28(14-12-27)20-5-2-17(3-6-20)23(25)29/h2-7,16,22H,8-15H2,1H3,(H2,25,29)(H,26,30)/t22-/m0/s1 Key: PNTVCCRNJOGKGA-QFIPXVFZSA-N; InChI=1/C24H30N4O3/c1-26-24(30)19-4-7-21-18(16-19)9-15-31-22(21)8-10-27-11-13-28(14-12-27)20-5-2-17(3-6-20)23(25)29/h2-7,16,22H,8-15H2,1H3,(H2,25,29)(H,26,30)/t22-/m0/s1 Key: PNTVCCRNJOGKGA-QFIPXVFZBB;
	SMILES NC(C(C=C1)=CC=C1N2CCN(CC[C@@H]3OCCC4=C3C=CC(C(NC)=O)=C4)CC2)=O;
Properties
Chemical formula	C24H30N4O3
Molar mass	422.529 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

PNU-142633 is an experimental drug candidate for the treatment of migraine. It exerts its effect as a selective, high affinity 5-HT_1D receptor antagonist.[1][2] PNU-142633 is well tolerated after oral administration.[3]

It was an interesting candidate due to its greater affinity for 5-HT_1D compared to 5-HT_1B receptors (typical migraine drugs such as triptans are agonists for both receptors), but experimental results were disappointing.[4]

The structure can be compared favorably with Sonepiprazole.

References

Pregenzer, JF; Alberts, GL; Im, WB; Slightom, JL; Ennis, MD; Hoffman, RL; Ghazal, NB; Tenbrink, RE (1999). "Differential pharmacology between the guinea-pig and the gorilla 5-HT1D receptor as probed with isochromans (5-HT1D-selective ligands)". British Journal of Pharmacology. 127 (2): 468–72. doi:10.1038/sj.bjp.0702532. PMC 1566017. PMID 10385247.
PNU 142633, Santa Cruz Biotechnology
Fleishaker, JC; Pearson, LK; Knuth, DW; Gomez-Mancilla, B; Francom, SF; McIntosh, MJ; Freestone, S; Azie, NE (1999). "Pharmacokinetics and tolerability of a novel 5-HT1D agonist, PNU-142633F". International Journal of Clinical Pharmacology and Therapeutics. 37 (10): 487–92. PMID 10543315.
The serotonin system : history, neuropharmacology, and pathology. M. D. Tricklebank, Eileen Daly. London, United Kingdom. 2019. ISBN 978-0-12-813324-8. OCLC 1105199268.{{cite book}}: CS1 maint: others (link)

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[1] Pregenzer, JF; Alberts, GL; Im, WB; Slightom, JL; Ennis, MD; Hoffman, RL; Ghazal, NB; Tenbrink, RE (1999). "Differential pharmacology between the guinea-pig and the gorilla 5-HT1D receptor as probed with isochromans (5-HT1D-selective ligands)". British Journal of Pharmacology. 127 (2): 468–72. doi:10.1038/sj.bjp.0702532. PMC 1566017. PMID 10385247.

[2] PNU 142633, Santa Cruz Biotechnology

[3] Fleishaker, JC; Pearson, LK; Knuth, DW; Gomez-Mancilla, B; Francom, SF; McIntosh, MJ; Freestone, S; Azie, NE (1999). "Pharmacokinetics and tolerability of a novel 5-HT1D agonist, PNU-142633F". International Journal of Clinical Pharmacology and Therapeutics. 37 (10): 487–92. PMID 10543315.

[4] The serotonin system : history, neuropharmacology, and pathology. M. D. Tricklebank, Eileen Daly. London, United Kingdom. 2019. ISBN 978-0-12-813324-8. OCLC 1105199268.{{cite book}}: CS1 maint: others (link)