Ifenprodil Explained

Verifiedfields:verified
Verifiedrevid:461742484
Tradename:Cerocral, Dilvax, Vadilex
Class:Cerebral vasodilators; NMDA receptor antagonists
Atc Prefix:C04
Atc Suffix:AX28
Cas Number:23210-56-2
Pubchem:3689
Iuphar Ligand:5472
Chemspiderid:3561
Unii:R8OE3P6O5S
Kegg:D08064
Chebi:93829
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: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:UYNVMODNBIQBMV-UHFFFAOYSA-N

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.[1] [2] [3] [4] 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,[5] specifically of NMDA receptors containing GluN1 and GluN2B subunits, the "ifenprodil binding site".[6] Additionally, ifenprodil inhibits GIRK channels[7] and interacts with α1-adrenergic, serotonin,[8] and sigma receptors.[9] [10] [11]

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.[12]

It is currently in phase II trials for cough and idiopathic pulmonary fibrosis, among other investigational uses.[13]

See also

Notes and References

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

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