Ifenprodil

Ifenprodil

Names
IUPAC name 4-[2-(4-benzylpiperidin-1-yl)-1-hydroxypropyl]phenol
Identifiers
ChEMBL	ChEMBL305187
ChemSpider	3561
IUPHAR/BPS	5472
Jmol interactive 3D	Image
KEGG	D08064
PubChem	3689
UNII	R8OE3P6O5S
InChI 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 Key: UYNVMODNBIQBMV-UHFFFAOYSA-N 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
SMILES OC(c1ccc(O)cc1)C(N2CCC(CC2)Cc3ccccc3)C
Properties
Chemical formula	C21H27NO2
Molar mass	325.445
Pharmacology
ATC code	C04AX28
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Ifenprodil is a selective inhibitor of the NMDA receptor.^[1] Its effect is specific to receptors composed of the GluN1 (glycine-binding NMDA receptor subunit 1) and GluN2B (glutamate-binding NMDA receptor subunit 2) subunits.^[2]

NMDA receptors are multimeric ionotropic 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 blocks NMDA receptors containing the GluN2B subunit.

References

1. Reynolds IJ, Miller RJ (1989). "Ifenprodil is a novel type of N-methyl-D-aspartate receptor antagonist: interaction with polyamines". Mol. Pharmacol. 36 (5): 758–65. PMID 2555674.
2. Korinek M, Kapras V, Vyklicky V, Adamusova E, Borovska J, Vales K, Stuchlik A, Horak M, Chodounska H, Vyklicky L Jr (Dec 2011). "Neurosteroid modulation of N-methyl-d-aspartate receptors: Molecular mechanism and behavioral effects". Steroids 76 (13): 1409–18. doi:10.1016/j.steroids.2011.09.002. PMID 21925193.