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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

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
New treatment options in intermittent claudication: the US experience.
2001 Apr
Naftidrofuryl in the treatment of vascular dementia.
2001 Dec
[Intermittent claudication. Walking plus vasoactive drug treatment].
2001 Jul 5
Inhibition of purified pig and human liver retinyl ester hydrolase by pharmacologic agents.
2001 May
Treatment alternatives for nocturnal leg cramps.
2001 May 21
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
Characterization of the CNS effects of naftidrofuryl (Praxilène) by quantitative EEG and functional MRI: a study in healthy elderly subjects.
2003
[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
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
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
Naftidrofuryl for intermittent claudication: meta-analysis based on individual patient data.
2009 Mar 10
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
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