SynCED: Naftidrofuryl

Record Information

Version

1.0

Creation Date

2009-07-03 21:54:23 UTC

Update Date

2026-05-14 19:35:01 UTC

Accession Number

CHEM002059

Identification

Common Name

Naftidrofuryl

Class

Small Molecule

Description

Naftidrofuryl (INN, also known as nafronyl or as the oxalate salt nafronyl oxalate) is a drug used in the management of peripheral and cerebral vascular disorders. It is claimed to enhance cellular oxidative capacity and to be a spasmolytic. It may also be a 5-HT2 receptor antagonist (2).

Contaminant Sources

STOFF IDENT Compounds
T3DB toxins

Contaminant Type

Amine
Drug
Ester
Ether
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Drosunal	Kegg
Artocoron	MeSH
Dusodril	MeSH
Lipha brand OF naftidrofuryl oxalate	MeSH
Merck brand OF nafronyl oxalate	MeSH
Nafti ratiopharm	MeSH
Nafti-puren	MeSH
Naftilux	MeSH
Oxalate, nafronyl	MeSH
Oxalate, naftifurin	MeSH
Praxilene	MeSH
Ratiopharm brand OF naftidrofuryl oxalate	MeSH
Alpharma brand OF naftidrofuryl oxalate	MeSH
Azunaftil	MeSH
Di actane	MeSH
Di-actane	MeSH
DiActane	MeSH
Gévatran	MeSH
Menarini brand OF naftidrofuryl oxalate	MeSH
Merck lipha santé brand 2 OF naftidrofuryl oxalate	MeSH
Nafronyl oxalate	MeSH
Nafronyloxalate	MeSH
Nafti-ratiopharm	MeSH
NaftiPuren	MeSH
Naftiratiopharm	MeSH
CT Arzneimittel brand OF naftidrofuryl oxalate	MeSH
CT-Arzneimittel brand OF naftidrofuryl oxalate	MeSH
Abbott brand OF naftidrofuryl oxalate	MeSH
Hexal brand OF naftidrofuryl oxalate	MeSH
Azupharma brand OF naftidrofuryl oxalate	MeSH
Faes brand OF naftidrofuryl oxalate	MeSH
Merck lipha santé brand 1 OF naftidrofuryl oxalate	MeSH
Nafti puren	MeSH
Naftifurin oxalate	MeSH
Naftilong	MeSH
Thérabel brand OF naftidrofuryl oxalate	MeSH
Nafti von CT	MeSH

Chemical Formula

C₂₄H₃₃NO₃

Average Molecular Mass

383.524 g/mol

Monoisotopic Mass

383.246 g/mol

CAS Registry Number

31329-57-4

IUPAC Name

2-(diethylamino)ethyl 3-(naphthalen-1-yl)-2-(oxolan-2-ylmethyl)propanoate

Traditional Name

naftidrofuryl

SMILES

CCN(CC)CCOC(=O)C(CC1CCCO1)CC1=C2C=CC=CC2=CC=C1

InChI Identifier

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

InChI Key

KBAFPSLPKGSANY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Not Available

Direct Parent

Naphthalenes

Alternative Parents

Substituents

Naphthalene
Fatty acid ester
Fatty acyl
Tetrahydrofuran
Amino acid or derivatives
Carboxylic acid ester
Tertiary amine
Tertiary aliphatic amine
Carboxylic acid derivative
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Carbonyl group
Organopnictogen compound
Organic nitrogen compound
Organic oxide
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Amine
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	190°C at 5.00E-01 mm Hg
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.00064 g/L	ALOGPS
logP	4.73	ALOGPS
logP	4.58	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Basic)	8.96	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	38.77 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	113.77 m³·mol⁻¹	ChemAxon
Polarizability	44.63 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Toxicity Profile

Route of Exposure

Oral (1).

Mechanism of Toxicity

Naftidrofuryl blocks the type 2 serotonin (5-HT2) receptors and thereby inhibits the effects of serotonin-induced vasoconstriction or platelet aggregation. It is also a stimulator of metabolism by improving aerobic glucose metabolism and by these means preserving cell function in ischemic conditions. Overdosage may result in disturbance of the atrioventricular conduction time, ventricular arrhythmia, convulsions, acute renal failure or acute hepatic necrosis (1).

Metabolism

Not Available

Toxicity Values

LD50: 1890 mg/kg (Oral, Rat) (4)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Naftidrofuryl is a drug used in the management of peripheral and cerebral vascular disorders (2).

Minimum Risk Level

Not Available

Health Effects

Naftidrofuryl increases the peripheric circulation of blood, e.g. in peripheral vascular disease (PAOD), Raynaud's phenomenon, cerebrovascular diseases, diffuse circulatory insufficiency in the elderly going along with confusion or behavioral disturbances. Overdosage may result in disturbance of the atrioventricular conduction time, ventricular arrhythmia, convulsions, acute renal failure or acute hepatic necrosis (1).

Symptoms

Convulsions, Nausea and epigastric pain, rash, hepatitis or hepatic failure, calcium oxalate stones (1, 3).

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB13588

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Naftidrofuryl

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

4417

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Naftidrofuryl (CHEM002059)

Structure for CHEM002059: Naftidrofuryl