U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry MIXED
Molecular Formula C24H33NO3.C6H8O7
Molecular Weight 575.6472
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NAFTIDROFURYL CITRATE

SMILES

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

InChI

InChIKey=LKLQMEYKQKAQCX-UHFFFAOYSA-N
InChI=1S/C24H33NO3.C6H8O7/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;7-3(8)1-6(13,5(11)12)2-4(9)10/h5-7,9-11,13,21-22H,3-4,8,12,14-18H2,1-2H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)

HIDE SMILES / InChI

Molecular Formula C6H8O7
Molecular Weight 192.1235
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
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
New treatment options in intermittent claudication: the US experience.
2001 Apr
Naftidrofuryl in quality of life (NIQOL). A Belgian study.
2001 Dec
Treatment alternatives for nocturnal leg cramps.
2001 May 21
[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
Findings of the Naftidrofuryl in Quality of Life (NIQOL) European study program.
2002 Mar
[Evidence-based therapy of intermittent claudication].
2004
[Secondary prevention and conservative therapy of obliterative arteriosclerosis].
2004 May 16
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
Management of peripheral arterial disease in the elderly: focus on cilostazol.
2008
Current management of intermittent claudication: the role of pharmacological and nonpharmacological symptom-directed therapies.
2009 Jul
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
by admin
on Sat Dec 16 09:40:58 GMT 2023
Edited
by admin
on Sat Dec 16 09:40:58 GMT 2023
Record UNII
1BB8I7MT98
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NAFTIDROFURYL CITRATE
Common Name English
NAFRONYL CITRATE
Common Name English
2-FURANPROPANOIC ACID, TETRAHYDRO-.ALPHA.-(1-NAPHTHALENYLMETHYL)-, 2-(DIETHYLAMINO)ETHYL ESTER, 2-HYDROXY-1,2,3-PROPANETRICARBOXYLATE (1:1)
Systematic Name English
Code System Code Type Description
ECHA (EC/EINECS)
286-639-8
Created by admin on Sat Dec 16 09:40:58 GMT 2023 , Edited by admin on Sat Dec 16 09:40:58 GMT 2023
PRIMARY
PUBCHEM
184479
Created by admin on Sat Dec 16 09:40:58 GMT 2023 , Edited by admin on Sat Dec 16 09:40:58 GMT 2023
PRIMARY
CAS
85293-34-1
Created by admin on Sat Dec 16 09:40:58 GMT 2023 , Edited by admin on Sat Dec 16 09:40:58 GMT 2023
PRIMARY
FDA UNII
1BB8I7MT98
Created by admin on Sat Dec 16 09:40:58 GMT 2023 , Edited by admin on Sat Dec 16 09:40:58 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE