Movatterモバイル変換

[0]ホーム
URL:

Jump to content
WikipediaThe Free Encyclopedia
Search

HP-505

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
HP-505
Identifiers
  • 3-phenyl-3H-spiro[isobenzofuran-1,4'-piperidine]
CAS Number
PubChemCID
ChemSpider
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC18H19NO
Molar mass265.356 g·mol−1
3D model (JSmol)
  • C1(C2OC3(CCNCC3)C4=C2C=CC=C4)=CC=CC=C1
  • InChI=1S/C18H19NO/c1-2-6-14(7-3-1)17-15-8-4-5-9-16(15)18(20-17)10-12-19-13-11-18/h1-9,17,19H,10-13H2
  • Key:ZFJQWOMHWFYLPD-UHFFFAOYSA-N

HP-505 is atriple reuptake inhibitor that was investigated byHoechst-Roussel Pharmaceuticals.[1] In mice, HP-505 was a potent inhibitor oftetrabenazine-inducedptosis which may indicate antidepressant activity.[2]

Pharmacology

[edit]
HP-505 IC50 (μM)[1]
5-HTNEDANE:5-HTDA:5-HT
0.19 ± 0.040.34 ± 0.10.66 ± 0.151.83.5

The inhibitory effect of HP-505 onserotonin reuptake is approximately 1.8 and 3.5 times stronger than onnorepinephrine anddopamine, respectively.[1] Subsequent investigations have found that HP-505 acts on presynaptic dopamine transporters and is devoid ofanticholinergic effects.[3]

Synthesis

[edit]

TheN-methylated analog is calledHP-365 [59142-29-9].

An older synthesis is available, although more modern methods exist now:[4]

HP-365 patent:[5]

References

[edit]
  1. ^abcMeyerson LR, Ong HH, Martin LL, Ellis DB (June 1980). "Effect of antidepressant agents on beta-adrenergic receptor and neurotransmitter regulatory systems".Pharmacology, Biochemistry, and Behavior.12 (6):943–948.doi:10.1016/0091-3057(80)90457-8.PMID 6105676.S2CID 45400599.
  2. ^Klioze SS, Bauer VJ, Geyer HM (April 1977). "Synthesis of spiro[isobenzofuran-1(3H),4'-piperidines] as potential central nervous system agents. 2. Compounds containing a heteroatom attached to nitrogen".Journal of Medicinal Chemistry.20 (4):610–612.doi:10.1021/jm00214a039.PMID 850252.
  3. ^Puri SK, Mantione CR, Petko W, Ellis DB (1979). "Spiroisobenzofuran Piperidine Derivatives. Interaction with Pre- and Post-Synaptic Dopaminergic Sites". In Usdin E, Kopin IJ, Barchas J (eds.).Catecholamines: Basic and Clinical Frontiers. Pergamon. pp. 514–516.doi:10.1016/B978-1-4832-8363-0.50158-0.ISBN 978-1-4832-8363-0.
  4. ^Maier, C. A., Wünsch, B. (1 January 2002). "Novel Spiropiperidines as Highly Potent and Subtype Selective σ-Receptor Ligands. Part 1".Journal of Medicinal Chemistry.45 (2):438–448.doi:10.1021/jm010992z.ISSN 0022-2623.
  5. ^Victor J. Bauer & Raymond W. Kosley, Jr.,U.S. patent 3,959,475 (1976 to CNA Holdings LLC).


Stub icon

Thisdrug article relating to thenervous system is astub. You can help Wikipedia byexpanding it.

Retrieved from "https://en.wikipedia.org/w/index.php?title=HP-505&oldid=1223662377"
Categories:
Hidden categories:
[8]ページ先頭
©2009-2025 Movatter.jp