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Details

Stereochemistry MIXED
Molecular Formula C24H33NO3.C4H4O4
Molecular Weight 499.5959
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of NAFTIDROFURYL FUMARATE

SMILES

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

InChI

InChIKey=UIBJEGDYQIIWSS-WLHGVMLRSA-N
InChI=1S/C24H33NO3.C4H4O4/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;5-3(6)1-2-4(7)8/h5-7,9-11,13,21-22H,3-4,8,12,14-18H2,1-2H3;1-2H,(H,5,6)(H,7,8)/b;2-1+

HIDE SMILES / InChI

Molecular Formula C24H33NO3
Molecular Weight 383.5237
Charge 0
Count
Stereochemistry MIXED
Additional Stereochemistry No
Defined Stereocenters 0 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

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
Screening of a chemical library reveals novel PXR-activating pharmacologic compounds.
2015-01-05
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.
2010-08
I suffer from frequent leg cramps and I've heard that quinine can help. Should I consider taking it?
2010-06
Silence of the limbs pharmacological symptomatic treatment of intermittent claudication.
2010-05
Assessment: symptomatic treatment for muscle cramps (an evidence-based review): report of the therapeutics and technology assessment subcommittee of the American academy of neurology.
2010-02-23
Current approach to the diagnosis and treatment of femoral-popliteal arterial disease. A systematic review.
2009-11
Vasodilators and vasoactive substances for idiopathic sudden sensorineural hearing loss.
2009-10-07
Fatal intoxication with naftidrofuryl.
2009-09
Assessment of binding affinity to 5-hydroxytryptamine 2A (5-HT2A) receptor and inverse agonist activity of naftidrofuryl: comparison with those of sarpogrelate.
2009-08
Current management of intermittent claudication: the role of pharmacological and nonpharmacological symptom-directed therapies.
2009-07
Pharmacologic therapy for intermittent claudication.
2009-05
Naftidrofuryl for intermittent claudication: meta-analysis based on individual patient data.
2009-03-10
Naftidrofuryl for intermittent claudication.
2008-04-16
Management of peripheral arterial disease in the elderly: focus on cilostazol.
2008
[Idiopathic sudden sensorineural hearing loss. What's the appropriate management?].
2007-10
Naftidrofuryl for acute stroke.
2007-04-18
A novel inhibitor of Mycobacterium tuberculosis pantothenate synthetase.
2007-02
Prognostic indicators of management of sudden sensorineural hearing loss in an Asian hospital.
2007-01
Peripheral arterial disease in the elderly.
2007
[Inpatient infusion treatment for acute tinnitus with and without adjuvant psychotherapeutic intervention. A comparison of psychological effectiveness].
2006-10
[Vasoactive agents and prostanoids in the therapy of PAD: facts, questions, disproven assumptions].
2006-08
Cost effectiveness of cilostazol compared with naftidrofuryl and pentoxifylline in the treatment of intermittent claudication in the UK.
2005-06
Acral necrosis after inadequate excessive administration of bleomycin in a testicular cancer patient.
2005-01
Therapy of hearing disorders - conservative procedures.
2005
Naftidrofuryl: a review of its use in the treatment of intermittent claudication.
2005
Pharmacokinetics of naftidrofuryl in patients with renal impairment.
2005
Calcium oxalate deposition in renal allografts: morphologic spectrum and clinical implications.
2004-08
[Secondary prevention and conservative therapy of obliterative arteriosclerosis].
2004-05-16
[Evidence-based therapy of intermittent claudication].
2004
Drug treatment of intermittent claudication.
2004
Raynaud's phenomenon (primary).
2003-06
Naftidrofuryl-induced liver injury.
2003-06
Naftidrofuryl-driven regulation of endothelial ICAM-1 involves nitric oxide.
2003-03-01
[Application of prostaglandin E1 and Naftidrofuryl in combined treatment of purulent-necrotic complications of the diabetic foot syndrome].
2003-01-29
Characterization of the CNS effects of naftidrofuryl (Praxilène) by quantitative EEG and functional MRI: a study in healthy elderly subjects.
2003
Can claudication be improved with medication?
2002-12
Nocturnal leg cramps in older people.
2002-10
Reduction of endothelin-1 binding and inhibition of endothelin-1-mediated detrusor contraction by naftidrofuryl.
2002-08
Vitamin A metabolism is altered in brown Norway and long-Evans rats infused with naftidrofuryl or erythromycin intravenously.
2002-07
Findings of the Naftidrofuryl in Quality of Life (NIQOL) European study program.
2002-03
Naftidrofuryl exerts antiserotonergic but no endothelin-receptor blocking effects in AS4.1 cells, juxtaglomerular cells and isolated perfused rat kidneys.
2002-01
[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
Naftidrofuryl in the treatment of vascular dementia.
2001-12
Naftidrofuryl in quality of life (NIQOL). A Belgian study.
2001-12
Pharmacotherapy of intermittent claudication.
2001-11
[Intermittent claudication. Walking plus vasoactive drug treatment].
2001-07-05
[Deleterious cardiac effects of serotonin in myocardial ischemia: role of naftidrofuryl].
2001-06
[Effect of naftidrofuryl on physiological walking distance in patients with intermittent claudication].
2001-04
Naftidrofuryl oxalate, nootropic effects on the scopolamine- and the basal forebrain lesion-induced amnesia in rats.
1991-08
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
Substance Class Chemical
Created
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on Wed Apr 02 10:49:45 GMT 2025
Edited
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Record UNII
S7WC2RUJ4H
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Name Type Language
NAFTIDROFURYL FUMARATE
Common Name English
2-FURANPROPIONIC ACID, TETRAHYDRO-.ALPHA.-(1-NAPHTHYLMETHYL)-, 2-(DIETHYLAMINO)ETHYL ESTER, FUMARATE (1:1)
Preferred Name English
Code System Code Type Description
FDA UNII
S7WC2RUJ4H
Created by admin on Wed Apr 02 10:49:45 GMT 2025 , Edited by admin on Wed Apr 02 10:49:45 GMT 2025
PRIMARY
CAS
4825-58-5
Created by admin on Wed Apr 02 10:49:45 GMT 2025 , Edited by admin on Wed Apr 02 10:49:45 GMT 2025
NON-SPECIFIC STOICHIOMETRY
PUBCHEM
6433358
Created by admin on Wed Apr 02 10:49:45 GMT 2025 , Edited by admin on Wed Apr 02 10:49:45 GMT 2025
PRIMARY
CAS
3200-07-5
Created by admin on Wed Apr 02 10:49:45 GMT 2025 , Edited by admin on Wed Apr 02 10:49:45 GMT 2025
PRIMARY
SMS_ID
100000181639
Created by admin on Wed Apr 02 10:49:45 GMT 2025 , Edited by admin on Wed Apr 02 10:49:45 GMT 2025
PRIMARY
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PARENT -> SALT/SOLVATE
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ACTIVE MOIETY