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Details

Stereochemistry MIXED
Molecular Formula C24H33NO3.C6H8O7
Molecular Weight 575.6472
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NAFTIDROFURYL CITRATE

SMILES

OC(=O)CC(O)(CC(O)=O)C(O)=O.CCN(CC)CCOC(=O)C(CC1CCCO1)CC2=C3C=CC=CC3=CC=C2

InChI

InChIKey=LKLQMEYKQKAQCX-UHFFFAOYSA-N
InChI=1S/C24H33NO3.C6H8O7/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;7-3(8)1-6(13,5(11)12)2-4(9)10/h5-7,9-11,13,21-22H,3-4,8,12,14-18H2,1-2H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/1369714

Naftidrofuryl (INN), also known as nafronyl or as the oxalate salt naftidrofuryl oxalate or nafronyl oxalate, is a vasodilator used in the management of peripheral and cerebral vascular disorders. The drug act as a selective antagonist of 5-HT2 receptors. Naftidrofuryl is marketed under a variety of trade names, including Artocoron, Azunaftil, Di-Actane, Dusodril, Enelbin, Frilix, Gevatran, Iridus, Iridux, Luctor, Nafti, Naftoling, Naftodril, Nafoxal, Praxilene, Sodipryl retard, and Vascuprax. Praxilene belongs to a group of medicines known as ‘metabolic activators’. These are used to treat different types of blood circulation problems. Praxilene allows the body to make better use of the oxygen in your blood. Praxilene is used to treat the following symptoms: cramp-like pains; cramps in legs at night; severe pain in r legs when people are resting (rest pain); pale or blue fingers or toes which get worse when it is cold; numbness, tingling or burning feelings in the fingers or toes (Raynaud’s syndrome or acrocyanosis); open sores on the legs or feet (trophic ulcers); poor circulation caused by diabetes (diabetic arteriopathy).

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.06 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Praxilene

Approved Use

Unknown

Launch Date

2016
PubMed

PubMed

TitleDatePubMed
Naftidrofuryl oxalate, nootropic effects on the scopolamine- and the basal forebrain lesion-induced amnesia in rats.
1991 Aug
Behavioral studies of the effects of moderate oligemic hypoxia caused by bilateral clamping of carotid arteries in mice. Impairment of spatial working memory.
1998 Jul-Oct
[Effect of naftidrofuryl on physiological walking distance in patients with intermittent claudication].
2001 Apr
New treatment options in intermittent claudication: the US experience.
2001 Apr
Naftidrofuryl in the treatment of vascular dementia.
2001 Dec
[Deleterious cardiac effects of serotonin in myocardial ischemia: role of naftidrofuryl].
2001 Jun
A new study demonstrates the efficacy of naftidrofuryl in the treatment of intermittent claudication. Findings of the Naftidrofuryl Clinical Ischemia Study (NCIS).
2001 Mar
Inhibition of purified pig and human liver retinyl ester hydrolase by pharmacologic agents.
2001 May
Treatment alternatives for nocturnal leg cramps.
2001 May 21
Pharmacotherapy of intermittent claudication.
2001 Nov
[Current EMNID survey on peripheral arterial occlusive disease].
2002
Effect of naftidrofuryl on intramuscular partial oxygen pressure (pO2) prior to, during and after physical load on the treadmill in apparently healthy subjects.
2002
Reduction of endothelin-1 binding and inhibition of endothelin-1-mediated detrusor contraction by naftidrofuryl.
2002 Aug
Vitamin A metabolism is altered in brown Norway and long-Evans rats infused with naftidrofuryl or erythromycin intravenously.
2002 Jul
Findings of the Naftidrofuryl in Quality of Life (NIQOL) European study program.
2002 Mar
[Application of prostaglandin E1 and Naftidrofuryl in combined treatment of purulent-necrotic complications of the diabetic foot syndrome].
2002 Nov-Dec
Nocturnal leg cramps in older people.
2002 Oct
Naftidrofuryl-induced liver injury.
2003 Jun
Calcium oxalate deposition in renal allografts: morphologic spectrum and clinical implications.
2004 Aug
[Secondary prevention and conservative therapy of obliterative arteriosclerosis].
2004 May 16
Acral necrosis after inadequate excessive administration of bleomycin in a testicular cancer patient.
2005 Jan
[Vasoactive agents and prostanoids in the therapy of PAD: facts, questions, disproven assumptions].
2006 Aug
[Inpatient infusion treatment for acute tinnitus with and without adjuvant psychotherapeutic intervention. A comparison of psychological effectiveness].
2006 Oct
Peripheral arterial disease in the elderly.
2007
Naftidrofuryl for acute stroke.
2007 Apr 18
A novel inhibitor of Mycobacterium tuberculosis pantothenate synthetase.
2007 Feb
Management of peripheral arterial disease in the elderly: focus on cilostazol.
2008
Naftidrofuryl for intermittent claudication: meta-analysis based on individual patient data.
2009 Mar 10
Current approach to the diagnosis and treatment of femoral-popliteal arterial disease. A systematic review.
2009 Nov
Muscle cramps: quinine derivatives likely to be effective but not recommended for routine use due to toxicity; vitamin B complex, naftidrofuryl and calcium channel blockers possibly effective.
2010 Aug
Patents

Patents

Sample Use Guides

The recommended dose is one or two capsules (100 mg naftidrofuryl oxalate) three times a day, for a minimum of three months
Route of Administration: Oral
In Vitro Use Guide
After culture in a rat serum enriched with naftidrofuryl at concentration of 20 uM, we observed a protective effect of this drug toward the disruption of axonal microtubules by vinka alkaloids
Name Type Language
NAFTIDROFURYL CITRATE
Common Name English
NAFRONYL CITRATE
Common Name English
2-FURANPROPANOIC ACID, TETRAHYDRO-.ALPHA.-(1-NAPHTHALENYLMETHYL)-, 2-(DIETHYLAMINO)ETHYL ESTER, 2-HYDROXY-1,2,3-PROPANETRICARBOXYLATE (1:1)
Systematic Name English
Code System Code Type Description
ECHA (EC/EINECS)
286-639-8
Created by admin on Sat Dec 16 09:40:58 GMT 2023 , Edited by admin on Sat Dec 16 09:40:58 GMT 2023
PRIMARY
PUBCHEM
184479
Created by admin on Sat Dec 16 09:40:58 GMT 2023 , Edited by admin on Sat Dec 16 09:40:58 GMT 2023
PRIMARY
CAS
85293-34-1
Created by admin on Sat Dec 16 09:40:58 GMT 2023 , Edited by admin on Sat Dec 16 09:40:58 GMT 2023
PRIMARY
FDA UNII
1BB8I7MT98
Created by admin on Sat Dec 16 09:40:58 GMT 2023 , Edited by admin on Sat Dec 16 09:40:58 GMT 2023
PRIMARY