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
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+
| 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 |
DescriptionCurator's Comment: description was created based on several sources, including
http://www.ncbi.nlm.nih.gov/pubmed/1369714
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).
CNS Activity
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2095200 Sources: http://www.ncbi.nlm.nih.gov/pubmed/1369714 |
0.06 µM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Praxilene Approved UseUnknown Launch Date2016 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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
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
Sources: http://www.ncbi.nlm.nih.gov/pubmed/7863151
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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| Record UNII |
S7WC2RUJ4H
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| Record Status |
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