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Ifenprodil

Chemical compound

Summary

Chemical compound

Field	Value
Verifiedfields	verified
verifiedrevid	461742484
image	Ifenprodil v2.svg
image_class	skin-invert-image
tradename	Cerocral, Dilvax, Vadilex
class	Cerebral vasodilators; NMDA receptor antagonists
ATC_prefix	C04
ATC_suffix	AX28
CAS_number_Ref
CAS_number	23210-56-2
PubChem	3689
IUPHAR_ligand	5472
ChemSpiderID_Ref
ChemSpiderID	3561
UNII_Ref
UNII	R8OE3P6O5S
KEGG_Ref
KEGG	D08064
ChEBI	93829
ChEMBL_Ref
ChEMBL	305187
synonyms	NP-120; NP 120; NP120; RC 61-91
IUPAC_name	4-[2-(4-benzylpiperidin-1-yl)-1-hydroxypropyl]phenol
C	21	H=27	N=1	O=2
SMILES	CC(C(C1=CC=C(C=C1)O)O)N2CCC(CC2)CC3=CC=CC=C3
StdInChI_Ref
StdInChI	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
StdInChIKey_Ref
StdInChIKey	UYNVMODNBIQBMV-UHFFFAOYSA-N

| Drugs.com =

| elimination_half-life =

Ifenprodil, sold under the brand names Cerocral, Dilvax, and Vadilex, is a cerebral vasodilator that has been marketed in some countries, including in Japan, Hong Kong, and France. It is currently under development for treatment of a variety of additional indications.

Ifenprodil has multiple known pharmacological actions. It is an inhibitor of the NMDA receptor, specifically of NMDA receptors containing GluN1 and GluN2B subunits, the "ifenprodil binding site". Additionally, ifenprodil inhibits GIRK channels and interacts with α1-adrenergic, serotonin, and sigma receptors.

Chemically, ifenprodil is a substituted phenethylamine and β-hydroxyamphetamine derivative. It is used pharmaceutically as the tartrate salt.

Research

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

It is currently in phase II trials for cough and idiopathic pulmonary fibrosis, among other investigational uses.

References

(2001). "The Merck Index". Merck Research Laboratories Division of Merck & Co., Inc..
(2014). "The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies". Springer US.
Schweizerischer Apotheker-Verein. (2004). "Index Nominum: International Drug Directory". Medpharm Scientific Publishers.
(2012). "Concise Dictionary of Pharmacological Agents: Properties and Synonyms". Springer Netherlands.
(November 1989). "Ifenprodil is a novel type of N-methyl-D-aspartate receptor antagonist: interaction with polyamines". Molecular Pharmacology.
(December 2011). "Neurosteroid modulation of N-methyl-D-aspartate receptors: molecular mechanism and behavioral effects". Steroids.
(March 2006). "Inhibition of G protein-activated inwardly rectifying K+ channels by ifenprodil". Neuropsychopharmacology.
(June 1995). "Ifenprodil inhibition of the 5-hydroxytryptamine3 receptor". Neuropharmacology.
(May 1993). "Further characterization of [3H]ifenprodil binding to sigma receptors in rat brain". European Journal of Pharmacology.
(January 1994). "Further characterization of [3H]ifenprodil binding in rat brain". European Journal of Pharmacology.
(February 1995). "Interactions of erythro-ifenprodil, threo-ifenprodil, erythro-iodoifenprodil, and eliprodil with subtypes of sigma receptors". European Journal of Pharmacology.
(2007). "Blockade of cochlear NMDA receptors prevents long-term tinnitus during a brief consolidation window after acoustic trauma". Hindawi Limited.
"Ifenprodil - Algernon Pharmaceuticals". Springer Nature Switzerland AG.

Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

alpha-blockers beta-hydroxyamphetamines experimental-drugs nmda-receptor-antagonists 4-hydroxyphenyl-compounds piperidines sigma-agonists vasodilators cerebral-vasodilators

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