Naftidrofuryl

Naftidrofuryl

Systematic (IUPAC) name
(RS)-2-(diethylamino)ethyl 3-(1-naphthyl)-2-(tetrahydrofuran-2-ylmethyl)propanoate
Clinical data
Trade names	Praxilene
AHFS/Drugs.com	International Drug Names
Legal status	UK: POM (Prescription only)
Routes of administration	Oral
Pharmacokinetic data
Metabolism	Hepatic
Biological half-life	1 - 3.5 hours
Identifiers
CAS Number	31329-57-4 Y
ATC code	C04AX21 (WHO)
PubChem	CID: 4417
ChemSpider	4264 Y
UNII	42H8PQ0NMJ Y
ChEMBL	CHEMBL1620794
Chemical data
Formula	C24H33NO3
Molecular mass	383.524 g/mol
SMILES O=C(OCCN(CC)CC)C(Cc2c1ccccc1ccc2)CC3OCCC3
InChI 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 Y Key:KBAFPSLPKGSANY-UHFFFAOYSA-N Y
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Naftidrofuryl (INN, also known as nafronyl or as the oxalate salt naftidrofuryl oxalate or nafronyl oxalate) is a drug used in the management of peripheral and cerebral vascular disorders as a vasodilator. It is also claimed to enhance cellular oxidative capacity, and may also be a 5-HT₂ receptor antagonist. It is also licensed for the treatment of intermittent claudication due to peripheral arterial disease.

Naftidrofuryl is marketed under the trade names Artocoron; Azunaftil; Di-Actane; Dusodril; Enelbin; Frilix; Gevatran; Iridus; Iridux; Luctor; Nafti; Naftoling; Naftodril; Nafoxal; Praxilene; Sodipryl retard; Vascuprax.

Historically, it has been used to treat sudden idiopathic hearing loss and acute tinnitus.

Naftidrofuryl may be effective for relieving the pain of muscle cramps.

Synthesis

Prepn: Szarvasi, Bayssat, FR 1363948  corresp to U.S. Patent 3,334,096 (1964, 1967 both to LIPHA); eidem

Adverse Effects

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