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Details

Stereochemistry MIXED
Molecular Formula C24H33NO3.C2H2O4
Molecular Weight 473.5586
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NAFRONYL OXALATE

SMILES

OC(=O)C(O)=O.CCN(CC)CCOC(=O)C(CC1CCCO1)CC2=CC=CC3=CC=CC=C23

InChI

InChIKey=SSAJNPNVUYMUCI-UHFFFAOYSA-N
InChI=1S/C24H33NO3.C2H2O4/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;3-1(4)2(5)6/h5-7,9-11,13,21-22H,3-4,8,12,14-18H2,1-2H3;(H,3,4)(H,5,6)

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

1.45186554E12
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
[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
Naftidrofuryl-induced liver injury.
2003 Jun
[Evidence-based therapy of intermittent claudication].
2004
Calcium oxalate deposition in renal allografts: morphologic spectrum and clinical implications.
2004 Aug
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
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
Naftidrofuryl for intermittent claudication.
2008 Apr 16
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
Name Type Language
NAFRONYL OXALATE
USAN  
USAN  
Official Name English
NAFTIDROFURYL OXALATE
MART.   WHO-DD  
Common Name English
NAFTIDROFURYL HYDROGEN OXALATE
EP  
Common Name English
NAFRONYL ACID OXALATE
MI  
Common Name English
NAFTIDROFURYL HYDROGEN OXALATE [EP MONOGRAPH]
Common Name English
2-(Diethylamino)ethyl tetrahydro-α-(1-naphthylmethyl)-2-furanpropionate oxalate (1:1)
Systematic Name English
PRAXILENE
Brand Name English
NAFTIDROFURYL OXALATE [JAN]
Common Name English
NAFRONYL OXALATE [USAN]
Common Name English
DUSODRIL
Brand Name English
DI-ACTANE
Brand Name English
CITOXID
Brand Name English
2-FURANPROPANOIC ACID, TETRAHYDRO-A-(1-NAPHTHALENYLMETHYL)-, 2-(DIETHYLAMINO)ETHYL ESTER, ETHANEDIOATE (1:1)
Common Name English
NAFTIDROFURYL OXALATE [MART.]
Common Name English
NSC-225233
Code English
EU-1806
Code English
LS-121
Code English
2-FURANPROPANOIC ACID, TETRAHYDRO-.ALPHA.-(1-NAPHTHALENYLMETHYL)-, 2-(DIETHYLAMINO)ETHYL ESTER, ETHANEDIOATE (1:1)
Common Name English
NAFRONYL ACID OXALATE [MI]
Common Name English
Naftidrofuryl oxalate [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29707
Created by admin on Fri Dec 15 15:01:24 UTC 2023 , Edited by admin on Fri Dec 15 15:01:24 UTC 2023
NCI_THESAURUS C66885
Created by admin on Fri Dec 15 15:01:24 UTC 2023 , Edited by admin on Fri Dec 15 15:01:24 UTC 2023
Code System Code Type Description
EPA CompTox
DTXSID6045533
Created by admin on Fri Dec 15 15:01:24 UTC 2023 , Edited by admin on Fri Dec 15 15:01:24 UTC 2023
PRIMARY
SMS_ID
100000085688
Created by admin on Fri Dec 15 15:01:24 UTC 2023 , Edited by admin on Fri Dec 15 15:01:24 UTC 2023
PRIMARY
RXCUI
7237
Created by admin on Fri Dec 15 15:01:24 UTC 2023 , Edited by admin on Fri Dec 15 15:01:24 UTC 2023
PRIMARY
CAS
3200-06-4
Created by admin on Fri Dec 15 15:01:24 UTC 2023 , Edited by admin on Fri Dec 15 15:01:24 UTC 2023
PRIMARY
MERCK INDEX
m7707
Created by admin on Fri Dec 15 15:01:24 UTC 2023 , Edited by admin on Fri Dec 15 15:01:24 UTC 2023
PRIMARY Merck Index
EVMPD
SUB03376MIG
Created by admin on Fri Dec 15 15:01:24 UTC 2023 , Edited by admin on Fri Dec 15 15:01:24 UTC 2023
PRIMARY
ChEMBL
CHEMBL1620794
Created by admin on Fri Dec 15 15:01:24 UTC 2023 , Edited by admin on Fri Dec 15 15:01:24 UTC 2023
PRIMARY
FDA UNII
5ADB8D9388
Created by admin on Fri Dec 15 15:01:24 UTC 2023 , Edited by admin on Fri Dec 15 15:01:24 UTC 2023
PRIMARY
NSC
225233
Created by admin on Fri Dec 15 15:01:24 UTC 2023 , Edited by admin on Fri Dec 15 15:01:24 UTC 2023
PRIMARY
PUBCHEM
18542
Created by admin on Fri Dec 15 15:01:24 UTC 2023 , Edited by admin on Fri Dec 15 15:01:24 UTC 2023
PRIMARY
ECHA (EC/EINECS)
221-703-0
Created by admin on Fri Dec 15 15:01:24 UTC 2023 , Edited by admin on Fri Dec 15 15:01:24 UTC 2023
PRIMARY
NCI_THESAURUS
C87286
Created by admin on Fri Dec 15 15:01:24 UTC 2023 , Edited by admin on Fri Dec 15 15:01:24 UTC 2023
PRIMARY