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Ifenprodil

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
Ifenprodil
Clinical data
Trade namesCerocral, Dilvax, Vadilex
Other namesNP-120; NP 120; NP120; RC 61-91
Drug classCerebral vasodilators;NMDA receptor antagonists
ATC code
Identifiers
  • 4-[2-(4-benzylpiperidin-1-yl)-1-hydroxypropyl]phenol
CAS Number
PubChemCID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.041.341Edit this at Wikidata
Chemical and physical data
FormulaC21H27NO2
Molar mass325.452 g·mol−1
3D model (JSmol)
  • CC(C(C1=CC=C(C=C1)O)O)N2CCC(CC2)CC3=CC=CC=C3
  • 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
  (verify)

Ifenprodil, sold under the brand namesCerocral,Dilvax, andVadilex, is acerebral vasodilator that has been marketed in some countries, including inJapan,Hong Kong, andFrance.[1][2][3][4] It is currently under development for treatment of a variety of additional indications.[5]

Ifenprodil has multiple knownpharmacological actions.[5] It is aninhibitor of theNMDA receptor,[6] specifically of NMDA receptors containingGluN1 andGluN2Bsubunits, the "ifenprodil binding site".[7] Additionally, ifenprodil inhibitsGIRK channels[8] and interacts withα1-adrenergic,[5]serotonin,[9] andsigmareceptors.[10][11][12][5]

Chemically, ifenprodil is asubstituted phenethylamine andβ-hydroxyamphetaminederivative.[2][3] It is usedpharmaceutically as thetartratesalt.[1][2][3]

Research

[edit]

Ifenprodil has been studied as a possible medication to preventtinnitus afteracoustic trauma.[13]

It is currently inphase II trials forcough andidiopathic pulmonary fibrosis, among other investigational uses.[5]

See also

[edit]
  • Traxoprodil (another β-hydroxyamphetamine NMDA receptor antagonist)

References

[edit]
  1. ^abThe Merck Index (Thirteenth ed.). Whitehouse Station, NJ: Merck Research Laboratories Division of Merck & Co., Inc. 2001. p. 878.
  2. ^abcElks J (2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 676.ISBN 978-1-4757-2085-3. Retrieved2 September 2024.
  3. ^abcSchweizerischer Apotheker-Verein (2004).Index Nominum: International Drug Directory. Medpharm Scientific Publishers. p. 625.ISBN 978-3-88763-101-7. Retrieved2 September 2024.
  4. ^Morton IK, Hall JM (2012).Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Netherlands. p. 150.ISBN 978-94-011-4439-1. Retrieved2 September 2024.
  5. ^abcde"Ifenprodil - Algernon Pharmaceuticals".AdisInsight. Springer Nature Switzerland AG. RetrievedMarch 25, 2021.
  6. ^Reynolds IJ, Miller RJ (November 1989). "Ifenprodil is a novel type of N-methyl-D-aspartate receptor antagonist: interaction with polyamines".Molecular Pharmacology.36 (5):758–765.doi:10.1016/S0026-895X(25)09662-2.PMID 2555674.
  7. ^Korinek M, Kapras V, Vyklicky V, Adamusova E, Borovska J, Vales K, et al. (December 2011). "Neurosteroid modulation of N-methyl-D-aspartate receptors: molecular mechanism and behavioral effects".Steroids.76 (13):1409–1418.doi:10.1016/j.steroids.2011.09.002.PMID 21925193.S2CID 195681796.
  8. ^Kobayashi T, Washiyama K, Ikeda K (March 2006)."Inhibition of G protein-activated inwardly rectifying K+ channels by ifenprodil".Neuropsychopharmacology.31 (3):516–524.doi:10.1038/sj.npp.1300844.PMID 16123769.
  9. ^McCool BA, Lovinger DM (June 1995). "Ifenprodil inhibition of the 5-hydroxytryptamine3 receptor".Neuropharmacology.34 (6):621–629.doi:10.1016/0028-3908(95)00030-a.PMID 7566498.
  10. ^Hashimoto K, London ED (May 1993)."Further characterization of [3H]ifenprodil binding to sigma receptors in rat brain".European Journal of Pharmacology.236 (1):159–163.doi:10.1016/0014-2999(93)90241-9.PMID 8319742.
  11. ^Hashimoto K, Mantione CR, Spada MR, Neumeyer JL, London ED (January 1994)."Further characterization of [3H]ifenprodil binding in rat brain".European Journal of Pharmacology.266 (1):67–77.doi:10.1016/0922-4106(94)90211-9.PMID 7907988.
  12. ^Hashimoto K, London ED (February 1995)."Interactions of erythro-ifenprodil, threo-ifenprodil, erythro-iodoifenprodil, and eliprodil with subtypes of sigma receptors".European Journal of Pharmacology.273 (3):307–310.doi:10.1016/0014-2999(94)00763-w.PMID 7737340.
  13. ^Guitton MJ, Dudai Y (2007)."Blockade of cochlear NMDA receptors prevents long-term tinnitus during a brief consolidation window after acoustic trauma".Neural Plasticity.2007 80904. Hindawi Limited.doi:10.1155/2007/80904.PMC 2246076.PMID 18301716.
Phenylethanolamine derivatives
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