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
Routes of administration	Oral
Legal status
Legal status	UK: POM (Prescription only)
Pharmacokinetic data
Metabolism	Hepatic
Biological half-life	1 - 3.5 hours
Identifiers
CAS Number	31329-57-4
ATC code	C04AX21 (WHO)
PubChem	CID 4417
ChemSpider	4264
UNII	42H8PQ0NMJ
ChEMBL	CHEMBL1620794
Chemical data
Formula	C24H33NO3
Molar 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 Key:KBAFPSLPKGSANY-UHFFFAOYSA-N
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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.^[1] 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.^[2]

Naftidrofuryl may be effective for relieving the pain of muscle cramps.^[3]

Synthesis

Prepn: Szarvasi, Bayssat, FR 1363948  corresp to U.S. Patent 3,334,096 (1964, 1967 both to LIPHA);^[4] eidem^[5]

Adverse Effects

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

References

1. Brayfield, A, ed. (14 January 2014). "Naftidrofuryl Oxalate". Martindale: The Complete Drug Reference. Pharmaceutical Press. Retrieved 6 August 2014.
2. http://www.der-arzneimittelbrief.de/Jahrgang2004/Ausgabe12Seite89.htm
3. Katzberg HD, Khan AH, So YT (February 2010). "Assessment: Symptomatic treatment for muscle cramps (an evidence-based review): Report of the Therapeutics and Technology Assessment Subcommittee of the American Academy of Neurology". Neurology 74 (8): 691–6. doi:10.1212/WNL.0b013e3181d0ccca. PMID 20177124.
4. Szarvasi et al., Compt. Rend. 260, 3095 (1965).
5. Bull. Soc. Chim. Fr. 1966, 1838.