Ifenprodil

Source: Wikipedia, the free encyclopedia.
Ifenprodil
Names
IUPAC name
4-[2-(4-Benzylpiperidin-1-yl)-1-hydroxypropyl]phenol
Identifiers
3D model (
JSmol
)
ChEMBL
ChemSpider
ECHA InfoCard
100.041.341 Edit this at Wikidata
IUPHAR/BPS
KEGG
UNII
  • InChI=1S/C21H27NO2/c1-16(21(24)19-7-9-20(23)10-8-19)22-13-11-18(12-14-22)15-17-5-3-2-4-6-17/h2-10,16,18,21,23-24H,11-15H2,1H3 checkY
    Key: UYNVMODNBIQBMV-UHFFFAOYSA-N checkY
  • InChI=1/C21H27NO2/c1-16(21(24)19-7-9-20(23)10-8-19)22-13-11-18(12-14-22)15-17-5-3-2-4-6-17/h2-10,16,18,21,23-24H,11-15H2,1H3
    Key: UYNVMODNBIQBMV-UHFFFAOYAU
  • OC(c1ccc(O)cc1)C(N2CCC(CC2)Cc3ccccc3)C
Properties
C21H27NO2
Molar mass 325.445
Pharmacology
C04AX28 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Ifenprodil is an inhibitor of the NMDA receptor,[1] specifically of GluN1 (glycine-binding NMDA receptor subunit 1) and GluN2B (glutamate-binding NMDA receptor subunit 2) subunits.[2] Additionally, ifenprodil inhibits GIRK channels, and interacts with alpha1 adrenergic, serotonin, and sigma receptors.[3]

NMDA receptors are multimeric

glutamate receptors composed of four subunits. GluN1
is obligate for functional expression. Other subunits include GluN2A, GluN2B, and the more recently discovered GluN3 subunits. Ifenprodil selectively inhibits NMDA receptors containing the GluN2B subunit.

As ifenprodil tartrate, it has been marketed in some countries, including Japan and France, as a cerebral vasodilator, under the trade names Cerocral, Dilvax, and Vadilex.[4]

Ifenprodil has been studied as a possible medication to prevent tinnitus after acoustic trauma.[5]

It is currently in

SARS-CoV2 infection and phase II trials for idiopathic pulmonary fibrosis.[6]

References

  1. .
  2. .
  3. .
  4. ^ The Merck Index (Thirteenth ed.). Whitehouse Station, NJ: Merck Research Laboratories Division of Merck & Co., Inc. 2001. p. 878.
  5. PMID 18301716
    .
  6. ^ "Ifenprodil - Algernon Pharmaceuticals - AdisInsight". adisinsight.springer.com. Retrieved March 25, 2021.