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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=CC=CC3=CC=CC=C23

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

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

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
[Effect of naftidrofuryl on physiological walking distance in patients with intermittent claudication].
2001 Apr
Naftidrofuryl in the treatment of vascular dementia.
2001 Dec
Naftidrofuryl in quality of life (NIQOL). A Belgian study.
2001 Dec
[Intermittent claudication. Walking plus vasoactive drug treatment].
2001 Jul 5
[Deleterious cardiac effects of serotonin in myocardial ischemia: role of naftidrofuryl].
2001 Jun
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
Can claudication be improved with medication?
2002 Dec
Naftidrofuryl exerts antiserotonergic but no endothelin-receptor blocking effects in AS4.1 cells, juxtaglomerular cells and isolated perfused rat kidneys.
2002 Jan
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
Characterization of the CNS effects of naftidrofuryl (Praxilène) by quantitative EEG and functional MRI: a study in healthy elderly subjects.
2003
Raynaud's phenomenon (primary).
2003 Jun
Naftidrofuryl-induced liver injury.
2003 Jun
Naftidrofuryl-driven regulation of endothelial ICAM-1 involves nitric oxide.
2003 Mar 1
[Evidence-based therapy of intermittent claudication].
2004
Drug treatment of intermittent claudication.
2004
Calcium oxalate deposition in renal allografts: morphologic spectrum and clinical implications.
2004 Aug
[Secondary prevention and conservative therapy of obliterative arteriosclerosis].
2004 May 16
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
Acral necrosis after inadequate excessive administration of bleomycin in a testicular cancer patient.
2005 Jan
Cost effectiveness of cilostazol compared with naftidrofuryl and pentoxifylline in the treatment of intermittent claudication in the UK.
2005 Jun
[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
Prognostic indicators of management of sudden sensorineural hearing loss in an Asian hospital.
2007 Jan
[Idiopathic sudden sensorineural hearing loss. What's the appropriate management?].
2007 Oct
Management of peripheral arterial disease in the elderly: focus on cilostazol.
2008
Naftidrofuryl for intermittent claudication.
2008 Apr 16
Assessment of binding affinity to 5-hydroxytryptamine 2A (5-HT2A) receptor and inverse agonist activity of naftidrofuryl: comparison with those of sarpogrelate.
2009 Aug
Current management of intermittent claudication: the role of pharmacological and nonpharmacological symptom-directed therapies.
2009 Jul
Naftidrofuryl for intermittent claudication: meta-analysis based on individual patient data.
2009 Mar 10
Pharmacologic therapy for intermittent claudication.
2009 May
Current approach to the diagnosis and treatment of femoral-popliteal arterial disease. A systematic review.
2009 Nov
Vasodilators and vasoactive substances for idiopathic sudden sensorineural hearing loss.
2009 Oct 7
Fatal intoxication with naftidrofuryl.
2009 Sep
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
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 Feb 23
I suffer from frequent leg cramps and I've heard that quinine can help. Should I consider taking it?
2010 Jun
Silence of the limbs pharmacological symptomatic treatment of intermittent claudication.
2010 May
Screening of a chemical library reveals novel PXR-activating pharmacologic compounds.
2015 Jan 5
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 Sat Dec 16 18:21:29 GMT 2023
Edited
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on Sat Dec 16 18:21:29 GMT 2023
Record UNII
S7WC2RUJ4H
Record Status Validated (UNII)
Record Version
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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)
Systematic Name English
Code System Code Type Description
FDA UNII
S7WC2RUJ4H
Created by admin on Sat Dec 16 18:21:29 GMT 2023 , Edited by admin on Sat Dec 16 18:21:29 GMT 2023
PRIMARY
CAS
4825-58-5
Created by admin on Sat Dec 16 18:21:29 GMT 2023 , Edited by admin on Sat Dec 16 18:21:29 GMT 2023
NON-SPECIFIC STOICHIOMETRY
PUBCHEM
6433358
Created by admin on Sat Dec 16 18:21:29 GMT 2023 , Edited by admin on Sat Dec 16 18:21:29 GMT 2023
PRIMARY
CAS
3200-07-5
Created by admin on Sat Dec 16 18:21:29 GMT 2023 , Edited by admin on Sat Dec 16 18:21:29 GMT 2023
PRIMARY
SMS_ID
100000181639
Created by admin on Sat Dec 16 18:21:29 GMT 2023 , Edited by admin on Sat Dec 16 18:21:29 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY