Page last updated: 2024-11-04

nafronyl

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Nafronyl: 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. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1310) It may also be an antagonist at 5HT-2 serotonin receptors. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID4417
CHEMBL ID1439099
CHEMBL ID1620794
CHEBI ID91817
SCHEMBL ID34062
MeSH IDM0014423

Synonyms (106)

Synonym
2-(diethylamino)ethyl 3-(naphthalen-1-yl)-2-(tetrahydrofuran-2-ylmethyl)propanoate
STL344054
BRD-A67862938-034-05-7
2-furanpropionic acid, tetrahydro-.alpha.-(1-naphthylmethyl)-, 2-(diethylamino)ethyl ester
2-furanpropanoic acid, tetrahydro-.alpha.-(1-naphthalenylmethyl)-, 2-(diethylamino)ethyl ester
KBIO1_000338
DIVK1C_000338
2-(diethylamino)ethyl 3-naphthalen-1-yl-2-(tetrahydrofuran-2-ylmethyl)propanoate
31329-57-4
nafronyl
SPECTRUM_001731
BSPBIO_003196
ls 84
naftidrofurilo [inn-spanish]
tridus
brn 1296059
tetrahydro-alpha-(1-naphthylmethyl)-2-furanpropanoic acid 2-(diethylamino)ethyl ester
c24h33no3
gevatran
naftidrofuryl [inn:ban]
2-furanpropanoic acid, tetrahydro-alpha-(1-naphthalenylmethyl)-, 2-(diethylamino)ethyl ester
2-furanpropionic acid, tetrahydro-alpha-(1-naphthylmethyl)-, 2-(diethylamino)ethyl ester
naftidrofurylum [inn-latin]
alpha-tetrahydrofurfuryl-1-naphthalenepropionic acid 2-(diethylamino)ethyl ester
n-diethylaminoethyl beta-(1-naphthyl)-beta-tetrahydrofuryl isobutyrate
naphtidrofuryl
2-(diethylamino)ethyl tetrahydro-alpha-(1-naphthylmethyl)-2-furanpropionate
3-(1-naphthyl)-2-tetrahydrofurfurylpropionic acid 2-(diethylamino)ethyl ester
einecs 250-572-2
naftidrofuryl
tetrahydro-alpha-(1-naphthalenylmethyl)-2-furanpropanoic acid 2-(diethylamino)ethyl ester
BSPBIO_000533
SPECTRUM5_001127
PRESTWICK3_000377
NCGC00178213-01
NCGC00178213-02
BPBIO1_000587
IDI1_000338
nafronyl oxalate(usan)
2-diethylaminoethyl 2-(1-naphthylmethyl)-3-tetrahydrofuran-2-yl-propanoate
nsc225233
2-furanpropionic acid, tetrahydro-.alpha.-(1-naphthylmethyl)-, 2-(diethylamino)ethyl esteroxalate (1:1)
2-(diethylamino)ethyl tetrahydro-.alpha.-(1-naphthylmethyl)-2-furanpropionate oxalate (1:1)
oxalte
2-furanpropanoic acid, tetrahydro-.alpha.-(1-naphthalenylmethyl)-, 2-(diethylamino)ethyl ester, ethanedioate (1:1)
2-(diethylamino)ethyl 3-(1-naphthyl)-2-(tetrahydro-2-furanylmethyl)propanoate oxalate
dubimax
AB00053667
KBIO3_002696
KBIO2_007347
KBIO2_004779
KBIO2_002211
KBIOGR_001489
KBIOSS_002211
PRESTWICK0_000377
PRESTWICK1_000377
SPECTRUM4_000855
SPECTRUM3_001598
SPBIO_002454
NINDS_000338
SPBIO_000915
SPECTRUM2_000868
PRESTWICK2_000377
drosunal (tn)
naftidrofuryl (inn)
D08244
AKOS005068111
CHEMBL1439099 ,
CHEMBL1620794
drosunal
bdbm50347133
42h8pq0nmj ,
naftidrofurylum
naftidrofurilo
unii-42h8pq0nmj
FT-0630558
naftidrofuryl [inn]
naftidrofuryl [who-dd]
tetrahydro-.alpha.-(1-naphthalenylmethyl)-2-furanpropanoic acid 2-(diethylamino)ethyl ester
2-(diethylamino)ethyl tetrahydro-.alpha.-(1-naphthylmethyl)-2-furanpropionate
tetrahydro-.alpha.-(1-naphthylmethyl)-2-furanpropionic acid 2-(diethylamino)ethyl ester
2-furanpropanoic acid, tetrahydro-a-(1-naphthalenylmethyl)-, 2-(diethylamino)ethyl ester
nafronyl [mi]
SCHEMBL34062
n-diethylaminoethyl .beta.-(1-naphthyl)-.beta.-tetrahydrofuryl isobutyrate
tetrahydro-.alpha.-(1-naphthylmethyl)-2-furanpropanoic acid 2-(diethylamino)ethyl ester
2-(diethylamino)ethyl ester tetrahydro-.alpha.-(1-naphthalenylmethyl)-2-furanpropanic acid
KBAFPSLPKGSANY-UHFFFAOYSA-N
.alpha.-tetrahydrofurfuryl-1-naphthalenepropionic acid 2-(diethylamino)ethyl ester
2-(diethylamino)ethyl 3-(1-naphthyl)-2-(tetrahydro-2-furanylmethyl)propanoate
2-(diethylamino)ethyl tetrahydro-.alpha.-(1-naphthylmethyl)-2-furanpropionate ester
dubimax (salt/mix)
2-(diethylamino)ethyl 3-(naphthalen-1-yl)-2-((tetrahydrofuran-2-yl)methyl)propanoate
AB00053667_10
DTXSID3023344
2-(1-naphthalenylmethyl)-3-(2-oxolanyl)propanoic acid 2-(diethylamino)ethyl ester
CHEBI:91817
J-018381
SBI-0051824.P002
Q425867
DB13588
2-(diethylamino)ethyl 2-(naphthalen-1-ylmethyl)-3-(oxolan-2-yl)propanoate
BRD-A67862938-034-09-9
NCGC00178213-04
EN300-7439215
2-(diethylamino)ethyl 3-(naphthalen-1-yl)-2-[(oxolan-2-yl)methyl]propanoate

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" According to our results, buflomedil is more effective and safe than naftidrofuryl in the treatment of patients with intermittent claudication."( Comparison of safety and efficacy of buflomedil and naftidrofuryl in the treatment of intermittent claudication.
Cerdeyra, C; Lucas, MA; Parano, JR; Rosas, G; Villa, JJ, 1981
)
0.26

Pharmacokinetics

ExcerptReferenceRelevance
"The present pharmacokinetic study of a drug used in geriatric patients with multiple diseases reveals that the half-life in the elderly was extended for about three times as long as in the corresponding control group."( [Pharmacokinetics of naftidrofuryl in multimorbidity in geriatric patients].
Horn, HJ; Mühlberg, W; Platt, D; Rieck, W; Schmitt-Rüth, R,
)
0.13

Bioavailability

ExcerptReferenceRelevance
" The bioavailability of its oral form, gelatin capsules, is good, if in the same person the area under the plasma curves after oral administration is compared to the one after intravenous injection."( [Pharmacokinetics and bioavailability of naftidrofuryl capsules in man].
D'Athis, P; Lartigue-Mattei, C; Lhoste, F; Tillement, JP, 1978
)
0.26
"The relative bioavailability of the vasodilator naftidrofuryl from formulations containing its oxalate or citrate salt has been estimated using a specific HPLC assay, and a less specific fluorimetric assay, to measure plasma drug concentrations."( Plasma concentrations and relative bioavailability of naftidrofuryl from different salt forms.
Alun-Jones, V; Brodie, RR; Chasseaud, LF; Hunter, JO; Taylor, T; Walmsley, LM; Wilkinson, PA,
)
0.13

Dosage Studied

ExcerptRelevanceReference
" Cumulative dose-response curves and maximal contraction in response to serotonin were recorded and this was repeated in the presence of NFT at 10(-6) and 10(-3) mol/l."( Serotonin-induced contractility in human saphenous vein is inhibited by naftidrofuryl.
Leathard, HL; O'Malley, MK; Sharp, EJ; Sian, M; Vashisht, R, 1992
)
0.28
" Naf shows a significant antithrombotic property, beginning with a dosage of 1 mg/kg which further increases relative to the dosage, and the stability of thrombi decreased."( Antithrombotic efficacy and its time course after application of naftidrofuryl in vivo.
Grosse-Heitmeyer, A; Herrmann, KS; Kreuzer, H, 1986
)
0.27
"In a single-blind study, 12 men (mean age 63 years) with senile dementia were given nafronyl in a dosage of 100 mg eight times daily for a week, followed by 100 mg four times daily for 12 weeks."( Effect of nafronyl on lactate and pyruvate in the cerebrospinal fluid of patients with senile dementia.
Berger, PA; Hollister, LE; Tinklenberg, JR; Yesavage, JA, 1982
)
0.89
" Cinnarizine potentiated the effect of PGI2 shifting the anti-hypoxic dose-response curve of PGI2 to the left."( Study on the anti-hypoxic effect of cinnarizine and its interaction with prostacyclin.
Milanova, D; Nikolov, R; Nikolova, M, 1984
)
0.27
" Since the vascular type of primary dementia is found to be associated with metabolic variations which resemble that of a cerebral hypoxia, hypoxic brain damage was produced by means of a sublethal dosage of cyanide in two-year-old rats."( The effect of naftidrofuryl on cyanide-induced hypoxic damage to glucose and energy metabolism in brain cortex of rats.
Hoyer, S, 1984
)
0.27
"A retrospective analysis was performed on all five published clinical trials in which naftidrofuryl was given at a dosage of 600 mg daily."( Naftidrofuryl in intermittent claudication: a retrospective analysis.
Brown, TM; Comte, S; Gamand, S; Lehert, P, 1994
)
0.29
" Evaluation criteria were pain assessment using a visual analogue scale, analgesic consumption considering both the power (WHO scale: level I paracetamol, level II dextropropoxyphene, level III morphine) and the dosage of the analgesic used (analgesic score), index of therapeutic success including the level of pain reduction and the absence of analgesic use."( [Evaluation of the analgesic effect of naftidrofuryl in permanent ischemia in patients with arterial diseases. Double-blind versus placebo study].
Glanddier, G; Guidicelli, H; Mosnier, M; Testart, J, 1994
)
0.29
" Cumulative dose-response curves were derived with and without NFT at 10(-9) and 10(-6) mol/l concentrations."( Microvascular disease and anastomotic dehiscence in the colon.
Dawson, PM; Fawcett, A; Nott, DM; O'Malley, MK; Shankar, A; Springall, RG; Vashisht, R, 1995
)
0.29
"5 years) of whom 49 had been treated orally with naftidrofuryl oxalate at a mean dosage of 485 +/- 120 mg/24h."( Calcium oxalate crystalluria in elderly patients and treatment with naftidrofuryl oxalate.
Bouthier, F; Charmes, JP; Leroux-Robert, C; Moesch, C, 1995
)
0.29
" Blood samples were taken over a period of 24 h after dosing for evaluation of the pharmacokinetics of naftidrofuryl."( Influence of age on the pharmacokinetics of naftidrofuryl after single oral administration in elderly versus young healthy volunteers.
Ahtoy, P; Bromet, M; Dupain, T; Gamand, S; Hulot, T, 1998
)
0.3
" Following an initial one month placebo run-in, patients were randomised to either naftidrofuryl, at a dosage of 200 mg three times daily, or matching placebo, for 6 months."( Naftidrofuryl can enhance the quality of life in patients with intermittent claudication.
Brown, TM; Lehert, P; Poth, J; Spengel, F, 1999
)
0.3
"Following an initial one month placebo run-in 235 patients, with stable IC for at least 3 months, were randomized to either naftidrofuryl (Praxilene), at a dosage of 200 mg three times daily, or matching placebo, for 6 months."( Naftidrofuryl in quality of life (NIQOL). A Belgian study.
Clement, DL; D'Hooge, D; Lehert, P, 2001
)
0.31
" Meta-analysis was neither possible nor considered appropriate due to the differences in the type of vasodilators used, dosage and duration of treatment."( Vasodilators and vasoactive substances for idiopathic sudden sensorineural hearing loss.
Agarwal, L; Pothier, DD, 2009
)
0.35
" Moreover, there were differences in the type, dosage and duration of vasodilator used in each study."( Vasodilators and vasoactive substances for idiopathic sudden sensorineural hearing loss.
Agarwal, L; Pothier, DD, 2009
)
0.35
" The proposed methods were validated according to ICH guidelines and were successfully applied for the determination of VN and NF in their tablet dosage forms."( Application of π acceptors to the spectrophotometric and spectrofluorimetric determination of vincamine and naftidrofuryl oxalate in their pharmaceutical preparations.
Badr El-Dien, MM; Elbrashy, AM; Ibrahim, FA; Nasr, JJM, 2017
)
0.46
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
naphthalenesAny benzenoid aromatic compound having a skeleton composed of two ortho-fused benzene rings.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (3)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
cytochrome P450 family 3 subfamily A polypeptide 4Homo sapiens (human)Potency0.47720.01237.983543.2770AID1645841
cytochrome P450 2D6Homo sapiens (human)Potency3.37860.00108.379861.1304AID1645840
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Bile salt export pumpHomo sapiens (human)IC50 (µMol)11.04000.11007.190310.0000AID1449628
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (22)

Processvia Protein(s)Taxonomy
fatty acid metabolic processBile salt export pumpHomo sapiens (human)
bile acid biosynthetic processBile salt export pumpHomo sapiens (human)
xenobiotic metabolic processBile salt export pumpHomo sapiens (human)
xenobiotic transmembrane transportBile salt export pumpHomo sapiens (human)
response to oxidative stressBile salt export pumpHomo sapiens (human)
bile acid metabolic processBile salt export pumpHomo sapiens (human)
response to organic cyclic compoundBile salt export pumpHomo sapiens (human)
bile acid and bile salt transportBile salt export pumpHomo sapiens (human)
canalicular bile acid transportBile salt export pumpHomo sapiens (human)
protein ubiquitinationBile salt export pumpHomo sapiens (human)
regulation of fatty acid beta-oxidationBile salt export pumpHomo sapiens (human)
carbohydrate transmembrane transportBile salt export pumpHomo sapiens (human)
bile acid signaling pathwayBile salt export pumpHomo sapiens (human)
cholesterol homeostasisBile salt export pumpHomo sapiens (human)
response to estrogenBile salt export pumpHomo sapiens (human)
response to ethanolBile salt export pumpHomo sapiens (human)
xenobiotic export from cellBile salt export pumpHomo sapiens (human)
lipid homeostasisBile salt export pumpHomo sapiens (human)
phospholipid homeostasisBile salt export pumpHomo sapiens (human)
positive regulation of bile acid secretionBile salt export pumpHomo sapiens (human)
regulation of bile acid metabolic processBile salt export pumpHomo sapiens (human)
transmembrane transportBile salt export pumpHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
protein bindingBile salt export pumpHomo sapiens (human)
ATP bindingBile salt export pumpHomo sapiens (human)
ABC-type xenobiotic transporter activityBile salt export pumpHomo sapiens (human)
bile acid transmembrane transporter activityBile salt export pumpHomo sapiens (human)
canalicular bile acid transmembrane transporter activityBile salt export pumpHomo sapiens (human)
carbohydrate transmembrane transporter activityBile salt export pumpHomo sapiens (human)
ABC-type bile acid transporter activityBile salt export pumpHomo sapiens (human)
ATP hydrolysis activityBile salt export pumpHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (12)

Processvia Protein(s)Taxonomy
basolateral plasma membraneBile salt export pumpHomo sapiens (human)
Golgi membraneBile salt export pumpHomo sapiens (human)
endosomeBile salt export pumpHomo sapiens (human)
plasma membraneBile salt export pumpHomo sapiens (human)
cell surfaceBile salt export pumpHomo sapiens (human)
apical plasma membraneBile salt export pumpHomo sapiens (human)
intercellular canaliculusBile salt export pumpHomo sapiens (human)
intracellular canaliculusBile salt export pumpHomo sapiens (human)
recycling endosomeBile salt export pumpHomo sapiens (human)
recycling endosome membraneBile salt export pumpHomo sapiens (human)
extracellular exosomeBile salt export pumpHomo sapiens (human)
membraneBile salt export pumpHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (2)

Assay IDTitleYearJournalArticle
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
AID1449628Inhibition of human BSEP expressed in baculovirus transfected fall armyworm Sf21 cell membranes vesicles assessed as reduction in ATP-dependent [3H]-taurocholate transport into vesicles incubated for 5 mins by Topcount based rapid filtration method2012Drug metabolism and disposition: the biological fate of chemicals, Dec, Volume: 40, Issue:12
Mitigating the inhibition of human bile salt export pump by drugs: opportunities provided by physicochemical property modulation, in silico modeling, and structural modification.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (393)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990205 (52.16)18.7374
1990's113 (28.75)18.2507
2000's48 (12.21)29.6817
2010's23 (5.85)24.3611
2020's4 (1.02)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 37.10

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index37.10 (24.57)
Research Supply Index6.30 (2.92)
Research Growth Index4.21 (4.65)
Search Engine Demand Index54.93 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (37.10)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials113 (26.34%)5.53%
Reviews47 (10.96%)6.00%
Case Studies26 (6.06%)4.05%
Observational0 (0.00%)0.25%
Other243 (56.64%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]