Basic information
- CAS
31329-57-4- Standard SMILES
CCN(CC)CCOC(=O)C(Cc1cccc2ccccc12)CC1CCCO1- InChIKey
KBAFPSLPKGSANY-UHFFFAOYSA-N- Molecular formula
- C24H33NO3
- Average molar mass
- 383.5 g/mol
- Monoisotopic mass
- 383.24604391
Overview
2-(1-naphthalenylmethyl)-3-(2-oxolanyl)propanoic acid 2-(diethylamino)ethyl ester is a member of naphthalenes.
Names & identifiers
- Preferred name
- Naftidrofuryl
- IUPAC
- 2-(diethylamino)ethyl 2-(naphthalen-1-ylmethyl)-3-(oxolan-2-yl)propanoate
- English name
- NAFRONYL
- Molecular formula
- C24H33NO3
- Molecular weight
- 383.53
Names & synonyms
nafronylNaftidrofuryl31329-57-4NaphtidrofurylTridusDubimaxGevatranNaftidrofuriloNaftidrofurylumDrosunal42H8PQ0NMJ2-(diethylamino)ethyl 2-(naphthalen-1-ylmethyl)-3-(oxolan-2-yl)propanoate
Show more names
CitoxidNafmnylDusodrilPraxileneDi-Actane
3-(1-Naphthyl)-2-tetrahydrofurfurylpropionic acid 2-(diethylamino)ethyl esterTetrahydro-alpha-(1-naphthalenylmethyl)-2-furanpropanoic acid 2-(diethylamino)ethyl esterDTXSID30233442-(Diethylamino)ethyl tetrahydro-alpha-(1-naphthylmethyl)-2-furanpropionatenaftidrofurileNaftifurin Oxalate2-FURANPROPANOIC ACID, TETRAHYDRO-A-(1-NAPHTHALENYLMETHYL)-, 2-(DIETHYLAMINO)ETHYL ESTERNaftiratiopharm
Database identifiers
- CAS
31329-57-4- PubChem CID
- 4417
- DTXSID
DTXSID3023344- ChEMBL
CHEMBL1443491、CHEMBL1620794- ChEBI
CHEBI:91817- UNII
- 42H8PQ0NMJ
Properties
Computed structural properties
- XLogP
- 4.8
- Topological polar surface area
- 38.8 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 11
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 465
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Used in Switzerland
Pharmaceuticals
Human DrugsPharmaceuticals
Endocrine DisruptorsPotential endocrine disrupting compound
Physicochemical properties
- Boiling point
- 0.5 · bp0.5 190°
- Density
- 431 · d431 1.0465
- refractive index
- 29 · nD29 1.5513
- storage temp.
- Refrigerator
- solubility
- Chloroform (Slightly), Ethyl Acetate (Slightly)
- form
- Oil
- pka
- 9.21 · 9.21±0.25(Predicted)
- color
- Colourless to Dark Yellow
- CAS DataBase Reference
- 31329 · 31329-57-4(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory InformationREACH registered substance: Naftidrofuryl (EC: 250-572-2)
Other Safety InformationIMAP assessments - 2-Furanpropanoic acid, tetrahydro-.alpha.-(1-naphthalenylmethyl)-, 2-(diethylamino)ethyl ester: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Toxicology
Health Effects
Naftidrofuryl 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 (A302).
Exposure RoutesOral (A302).
Toxicity Summary
Naftidrofuryl 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 (A302).
Chemistry & industry
Pharmacology
ATC Code
C04AX21
C - Cardiovascular system
QC - Cardiovascular system
MeSH Pharmacological Classification
Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or SEROTONIN RECEPTOR AGONISTS.
Drugs used to cause dilation of the blood vessels.
Uses & manufacturing
Uses
Use (kg; approx.) in Germany (2009): >5000
Naftidrofuryl is a drug used in the management of peripheral and cerebral vascular disorders (L999).
Use ClassificationPharmaceuticals
Applications
UsesVasodilator.
UsesNafronyl is a selective inhibitor of serotonin receptors. Nafronyl is a vasodilator used in the treatment of intermittent claudication.
Upstream & downstream products
Upstream raw materials
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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