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Naftidrofuryl

Chemical compound From Wikipedia, the free encyclopedia

Naftidrofuryl, also known as nafronyl and sold under the brand name Praxilene among others, is a serotonin 5-HT2 receptor antagonist which is used as a vasodilator in the treatment of peripheral and cerebral vascular disorders.[1][2][3][4][5] It is taken orally.[1]

Trade namesPraxilene, others
Other namesNafronyl; Naftidrofurile; Naftifurine; EU-1806; EU1806; LS-121; LS121
Quick facts Clinical data, Trade names ...
Naftidrofuryl
Clinical data
Trade namesPraxilene, others
Other namesNafronyl; Naftidrofurile; Naftifurine; EU-1806; EU1806; LS-121; LS121
AHFS/Drugs.comInternational Drug Names
Routes of
administration
Oral[1]
Drug classSerotonin 5-HT2A receptor antagonist; Vasodilator
ATC code
Legal status
Legal status
  • UK: POM (Prescription only)
Pharmacokinetic data
Bioavailability20–78% (in different studies)[1]
Protein binding80%[1]
MetabolismHepatic[1]
Onset of action0.8–1.0 hours (TmaxTooltip time to peak levels)[1]
Elimination half-life1.2–2 hours[1]
Duration of action2–3 hours[1]
Identifiers
  • (RS)-2-(diethylamino)ethyl 3-(1-naphthyl)-2-(tetrahydrofuran-2-ylmethyl)propanoate
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.045.960 Edit this at Wikidata
Chemical and physical data
FormulaC24H33NO3
Molar mass383.532 g·mol−1
3D model (JSmol)
  • O=C(OCCN(CC)CC)C(Cc2c1ccccc1ccc2)CC3OCCC3
  • InChI=1S/C24H33NO3/c1-3-25(4-2)14-16-28-24(26)21(18-22-12-8-15-27-22)17-20-11-7-10-19-9-5-6-13-23(19)20/h5-7,9-11,13,21-22H,3-4,8,12,14-18H2,1-2H3 checkY
  • Key:KBAFPSLPKGSANY-UHFFFAOYSA-N checkY
  (verify)
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Medical uses

Naftidrofuryl is used as a vasodilator in the treatment of peripheral and cerebral vascular disorders.[1][2][5] It is also licensed for the treatment of intermittent claudication due to peripheral arterial disease.[1] Historically, it has been used to treat sudden idiopathic hearing loss and acute tinnitus.[6] Naftidrofuryl may be effective for relieving the pain of muscle cramps.[7]

Adverse effects

Naftidrofuryl has been associated with nausea, abdominal pain, and rash.[8][1] Rarely, hepatitis and liver failure have been reported.[1][8]

Pharmacology

Pharmacodynamics

Naftidrofuryl acts as a selective antagonist of 5-HT2 receptors (with action as an inverse agonist of the 5-HT2A receptor specifically characterized).[1][5][9][10]

Pharmacokinetics

The oral bioavailability of naftidrofuryl is 20 to 78% in different studies.[1] Its time to peak levels is 0.8 to 1.0 hours.[1] There is some evidence that naftidrofuryl crosses the blood–brain barrier and penetrates into the central nervous system.[11][12] The drug's plasma protein binding is 80%.[1] It is metabolized in the liver.[1] The elimination half-life of naftidrofuryl is 1.2 to 2 hours.[1] Its half-life is longer in the elderly than in younger people.[1] The drug's duration of effects is 2 to 3 hours and closely parallels circulating levels of naftidrofuryl.[1]

History

Naftidrofuryl was first described in the scientific literature by at least 1966.[4]

Society and culture

Names

Naftidrofuryl is the generic name of the drug and its (INNTooltip International Nonproprietary Name, BANTooltip British Approved Name, DCFTooltip Dénomination Commune Française, and JANTooltip Japanese Accepted Name.[2][3][4][5] It is also known as naftidrofurile (DCITTooltip Denominazione Comune Italiana) or as nafronyl (USANTooltip United States Adopted Name.[2][3][4][5] Naftidrofuryl is marketed under a variety of trade names, including Artocoron, Azunaftil, Di-Actane, Dusodril, Enelbin, Frilix, Gevatran, Iridus, Iridux, Luctor, Nafti, Naftilong, Naftodril, Nafoxal, Praxilene, Sodipryl Retard, Stimlor, and Vascuprax, among others.[2][3][4]

Availability

Naftidrofuryl is marketed and used widely throughout the world.[2][3]

See also

References

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