Ifenprodil

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
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.041.341 Edit 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 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.[5]

Ifenprodil has multiple known pharmacological actions.[5] It is an inhibitor of the NMDA receptor,[6] specifically of NMDA receptors containing GluN1 and GluN2B subunits, the "ifenprodil binding site".[7] Additionally, ifenprodil inhibits GIRK channels[8] and interacts with α1-adrenergic,[5] serotonin,[9] and sigma receptors.[10][11][12][5]

Chemically, ifenprodil is a substituted phenethylamine and β-hydroxyamphetamine derivative.[2][3] It is used pharmaceutically as the tartrate salt.[1][2][3]

Research

Ifenprodil has been studied as a possible medication to prevent tinnitus after acoustic trauma.[13]

It is currently in phase II trials for cough and idiopathic pulmonary fibrosis, among other investigational uses.[5]

See also

  • Traxoprodil (another β-hydroxyamphetamine NMDA receptor antagonist)

References

  1. ^ a b The Merck Index (Thirteenth ed.). Whitehouse Station, NJ: Merck Research Laboratories Division of Merck & Co., Inc. 2001. p. 878.
  2. ^ a b c Elks J (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 676. ISBN 978-1-4757-2085-3. Retrieved 2 September 2024.
  3. ^ a b c Schweizerischer Apotheker-Verein (2004). Index Nominum: International Drug Directory. Medpharm Scientific Publishers. p. 625. ISBN 978-3-88763-101-7. Retrieved 2 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. Retrieved 2 September 2024.
  5. ^ a b c d e "Ifenprodil - Algernon Pharmaceuticals". AdisInsight. Springer Nature Switzerland AG. Retrieved March 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. 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. Hindawi Limited: 80904. doi:10.1155/2007/80904. PMC 2246076. PMID 18301716.

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