Naftidrofuryl (T3D2474)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (3)XML
Targets (3)
Record Information
Version2.0
Creation Date2009-07-03 21:54:23 UTC
Update Date2014-12-24 20:25:33 UTC
Accession NumberT3D2474
Identification
Common NameNaftidrofuryl
ClassSmall Molecule
DescriptionNaftidrofuryl (INN, also known as nafronyl or as the oxalate salt nafronyl oxalate) is a drug used in the management of peripheral and cerebral vascular disorders. It is claimed to enhance cellular oxidative capacity and to be a spasmolytic. It may also be a 5-HT2 receptor antagonist (2).
Compound Type
  • Amine
  • Drug
  • Ester
  • Ether
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
Drosunal
Dubimax
Dusodril
Gevatran
Iridus
Nafronyl
Nafronyl oxalate
Nafronyl oxalate(usan)
Nafronyloxalate
Naftidrofurilo
Naftidrofuryl oxalate
Naftidrofurylum
Naftifurin oxalate
Naphtidrofuryl
Praxilene
Tridus
Chemical FormulaC24H33NO3
Average Molecular Mass383.524 g/mol
Monoisotopic Mass383.246 g/mol
CAS Registry Number31329-57-4
IUPAC Name2-(diethylamino)ethyl 3-(naphthalen-1-yl)-2-(oxolan-2-ylmethyl)propanoate
Traditional Namenaftidrofuryl
SMILESCCN(CC)CCOC(=O)C(CC1CCCO1)CC1=C2C=CC=CC2=CC=C1
InChI IdentifierInChI=1S/C24H33NO3/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/h5-7,9-11,13,21-22H,3-4,8,12,14-18H2,1-2H3
InChI KeyInChIKey=KBAFPSLPKGSANY-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNot Available
Direct ParentNaphthalenes
Alternative Parents
Substituents
  • Naphthalene
  • Fatty acid ester
  • Fatty acyl
  • Tetrahydrofuran
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Tertiary amine
  • Tertiary aliphatic amine
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Organoheterocyclic compound
  • Carbonyl group
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Amine
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling Point190°C at 5.00E-01 mm Hg
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00064 g/LALOGPS
logP4.73ALOGPS
logP4.58ChemAxon
logS-5.8ALOGPS
pKa (Strongest Basic)8.96ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area38.77 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity113.77 m³·mol⁻¹ChemAxon
Polarizability44.63 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-9120000000-58acd41b3b73264d36172021-09-24View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-2549000000-3701aef880e3113e81742016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udr-9822000000-8205fc5c8916c186cad32016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0v6r-8920000000-7c3b1ec379dfac422f842016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-3059000000-dabb68bdf42dd117b1b62016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001r-6295000000-6891e2b71701c4e8a67c2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dr-9340000000-468b51b4371edaf437a22016-08-03View Spectrum
MSMass Spectrum (Electron Ionization)splash10-000i-9100000000-d75c1dd41b1e807c5df52014-09-20View Spectrum
Toxicity Profile
Route of ExposureOral (1).
Mechanism of ToxicityNaftidrofuryl blocks the type 2 serotonin (5-HT2) receptors and thereby inhibits the effects of serotonin-induced vasoconstriction or platelet aggregation. It is also a stimulator of metabolism by improving aerobic glucose metabolism and by these means preserving cell function in ischemic conditions. Overdosage may result in disturbance of the atrioventricular conduction time, ventricular arrhythmia, convulsions, acute renal failure or acute hepatic necrosis (1).
MetabolismNot Available
Toxicity ValuesLD50: 1890 mg/kg (Oral, Rat) (4)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNaftidrofuryl is a drug used in the management of peripheral and cerebral vascular disorders (2).
Minimum Risk LevelNot Available
Health EffectsNaftidrofuryl increases the peripheric circulation of blood, e.g. in peripheral vascular disease (PAOD), Raynaud's phenomenon, cerebrovascular diseases, diffuse circulatory insufficiency in the elderly going along with confusion or behavioral disturbances. Overdosage may result in disturbance of the atrioventricular conduction time, ventricular arrhythmia, convulsions, acute renal failure or acute hepatic necrosis (1).
SymptomsConvulsions, Nausea and epigastric pain, rash, hepatitis or hepatic failure, calcium oxalate stones (1, 3).
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID4417
ChEMBL IDCHEMBL1620794
ChemSpider ID4264
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDTETRA-H-BIOPTERIN
CTD IDD009257
Stitch IDNaftidrofuryl
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
  1. Koller MF, Schmid M, Iten PX, Vonlanthen B, Bar W: Fatal intoxication with naftidrofuryl. Leg Med (Tokyo). 2009 Sep;11(5):229-33. doi: 10.1016/j.legalmed.2009.04.003. Epub 2009 Jun 10. [19520596 ]
  2. Wikipedia. Naftidrofuryl. Last Updated 16 July 2009. [Link]
  3. MIMS Hong Kong (2009). Drug Info: Naftidrofuryl. [Link]
  4. Lookchem (2008). Naftidrofuryl. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. 5-hydroxytryptamine receptor 2A
General Function:
Virus receptor activity
Specific Function:
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI) and lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors. Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways. Signaling activates phospholipase C and a phosphatidylinositol-calcium second messenger system that modulates the activity of phosphatidylinositol 3-kinase and promotes the release of Ca(2+) ions from intracellular stores. Affects neural activity, perception, cognition and mood. Plays a role in the regulation of behavior, including responses to anxiogenic situations and psychoactive substances. Plays a role in intestinal smooth muscle contraction, and may play a role in arterial vasoconstriction.(Microbial infection) Acts as a receptor for human JC polyomavirus/JCPyV.
Gene Name:
HTR2A
Uniprot ID:
P28223
Molecular Weight:
52602.58 Da
References
  1. Marconi A, Darquenne S, Boulmerka A, Mosnier M, D'Alessio P: Naftidrofuryl-driven regulation of endothelial ICAM-1 involves nitric oxide. Free Radic Biol Med. 2003 Mar 1;34(5):616-25. [12614850 ]
Target Details
2. 5-hydroxytryptamine receptor 2B
General Function:
Serotonin receptor activity
Specific Function:
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various ergot alkaloid derivatives and psychoactive substances. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors. Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways. Signaling activates a phosphatidylinositol-calcium second messenger system that modulates the activity of phosphatidylinositol 3-kinase and down-stream signaling cascades and promotes the release of Ca(2+) ions from intracellular stores. Plays a role in the regulation of dopamine and 5-hydroxytryptamine release, 5-hydroxytryptamine uptake and in the regulation of extracellular dopamine and 5-hydroxytryptamine levels, and thereby affects neural activity. May play a role in the perception of pain. Plays a role in the regulation of behavior, including impulsive behavior. Required for normal proliferation of embryonic cardiac myocytes and normal heart development. Protects cardiomyocytes against apoptosis. Plays a role in the adaptation of pulmonary arteries to chronic hypoxia. Plays a role in vasoconstriction. Required for normal osteoblast function and proliferation, and for maintaining normal bone density. Required for normal proliferation of the interstitial cells of Cajal in the intestine.
Gene Name:
HTR2B
Uniprot ID:
P41595
Molecular Weight:
54297.41 Da
References
  1. Marconi A, Darquenne S, Boulmerka A, Mosnier M, D'Alessio P: Naftidrofuryl-driven regulation of endothelial ICAM-1 involves nitric oxide. Free Radic Biol Med. 2003 Mar 1;34(5):616-25. [12614850 ]
Target Details
3. 5-hydroxytryptamine receptor 2C
General Function:
Serotonin receptor activity
Specific Function:
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including ergot alkaloid derivatives, 1-2,5,-dimethoxy-4-iodophenyl-2-aminopropane (DOI) and lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors. Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways. Signaling activates a phosphatidylinositol-calcium second messenger system that modulates the activity of phosphatidylinositol 3-kinase and down-stream signaling cascades and promotes the release of Ca(2+) ions from intracellular stores. Regulates neuronal activity via the activation of short transient receptor potential calcium channels in the brain, and thereby modulates the activation of pro-opiomelacortin neurons and the release of CRH that then regulates the release of corticosterone. Plays a role in the regulation of appetite and eating behavior, responses to anxiogenic stimuli and stress. Plays a role in insulin sensitivity and glucose homeostasis.
Gene Name:
HTR2C
Uniprot ID:
P28335
Molecular Weight:
51820.705 Da
References
  1. Marconi A, Darquenne S, Boulmerka A, Mosnier M, D'Alessio P: Naftidrofuryl-driven regulation of endothelial ICAM-1 involves nitric oxide. Free Radic Biol Med. 2003 Mar 1;34(5):616-25. [12614850 ]