Etilefrine

Identification

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Name
Etilefrine
Accession Number
DB08985
Type
Small Molecule
Groups
Withdrawn
Description

Etilefrine is an adrenergic agonist that appears to interact with beta-2 and some alpha adrenergic receptors. It has been used as a vasoconstrictor agent.

Structure
Thumb
Synonyms
  • Etilefrina
Categories
UNII
ZB6F8MY53V
CAS number
709-55-7
Weight
Average: 181.2316
Monoisotopic: 181.110278729
Chemical Formula
C10H15NO2
InChI Key
SQVIAVUSQAWMKL-UHFFFAOYSA-N
InChI
InChI=1S/C10H15NO2/c1-2-11-7-10(13)8-4-3-5-9(12)6-8/h3-6,10-13H,2,7H2,1H3
IUPAC Name
3-[2-(ethylamino)-1-hydroxyethyl]phenol
SMILES
CCNCC(O)C1=CC(O)=CC=C1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic AcidThe risk or severity of hypertension can be increased when 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid is combined with Etilefrine.
1-benzylimidazoleThe risk or severity of hypertension can be increased when 1-benzylimidazole is combined with Etilefrine.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of adverse effects can be increased when 2,5-Dimethoxy-4-ethylamphetamine is combined with Etilefrine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when Etilefrine is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3-isobutyl-1-methyl-7H-xanthineThe risk or severity of adverse effects can be increased when Etilefrine is combined with 3-isobutyl-1-methyl-7H-xanthine.
3,5-diiodothyropropionic acidThe risk or severity of adverse effects can be increased when Etilefrine is combined with 3,5-diiodothyropropionic acid.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Etilefrine.
4-MethoxyamphetamineThe risk or severity of hypertension can be increased when 4-Methoxyamphetamine is combined with Etilefrine.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of hypertension can be increased when Etilefrine is combined with 5-methoxy-N,N-dimethyltryptamine.
6-O-benzylguanineThe risk or severity of adverse effects can be increased when Etilefrine is combined with 6-O-benzylguanine.
Additional Data Available
  • Extended Description
    Extended Description

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Evidence Level

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Food Interactions
Not Available

References

Synthesis Reference

British Patent 1,358,973.

General References
Not Available
External Links
KEGG Drug
D07931
PubChem Compound
3306
PubChem Substance
310264946
ChemSpider
3190
BindingDB
97154
ChEBI
91518
ChEMBL
CHEMBL86882
Wikipedia
Etilefrine
ATC Codes
C01CA51 — Etilefrine, combinationsC01CA01 — Etilefrine

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)208-209British Patent 1,358,973.
Predicted Properties
PropertyValueSource
Water Solubility13.8 mg/mLALOGPS
logP0.01ALOGPS
logP0.23ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)9.1ChemAxon
pKa (Strongest Basic)9.73ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area52.49 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity52 m3·mol-1ChemAxon
Polarizability19.78 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-05no-3900000000-dc75520c0fb8e17d3ef6

Taxonomy

Description
This compound belongs to the class of organic compounds known as 1-hydroxy-4-unsubstituted benzenoids. These are phenols that are unsubstituted at the 4-position.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenols
Sub Class
1-hydroxy-4-unsubstituted benzenoids
Direct Parent
1-hydroxy-4-unsubstituted benzenoids
Alternative Parents
Aralkylamines / 1-hydroxy-2-unsubstituted benzenoids / Benzene and substituted derivatives / Secondary alcohols / 1,2-aminoalcohols / Dialkylamines / Organopnictogen compounds / Hydrocarbon derivatives / Aromatic alcohols
Substituents
1-hydroxy-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid / Aralkylamine / Monocyclic benzene moiety / 1,2-aminoalcohol / Secondary alcohol / Secondary aliphatic amine / Secondary amine / Alcohol / Organopnictogen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Drug created on June 10, 2014 11:55 / Updated on May 01, 2019 10:48