Etilefrine

Identification

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Withdrawn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
Not Available
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
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
DrugInteractionDrug group
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Etilefrine.Approved, Investigational
AcepromazineAcepromazine may decrease the vasoconstricting activities of Etilefrine.Approved, Vet Approved
AlfuzosinAlfuzosin may decrease the vasoconstricting activities of Etilefrine.Approved, Investigational
AmitriptylineAmitriptyline may decrease the vasoconstricting activities of Etilefrine.Approved
AmoxapineAmoxapine may decrease the vasoconstricting activities of Etilefrine.Approved
AmphetamineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Etilefrine.Approved, Illicit, Investigational
AripiprazoleAripiprazole may decrease the vasoconstricting activities of Etilefrine.Approved, Investigational
AsenapineAsenapine may decrease the vasoconstricting activities of Etilefrine.Approved
AtomoxetineAtomoxetine may increase the hypertensive activities of Etilefrine.Approved
BenzphetamineThe risk or severity of adverse effects can be increased when Benzphetamine is combined with Etilefrine.Approved, Illicit
Benzylpenicilloyl PolylysineEtilefrine may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.Approved
BevantololBevantolol may decrease the vasoconstricting activities of Etilefrine.Approved
BrexpiprazoleBrexpiprazole may decrease the vasoconstricting activities of Etilefrine.Approved, Investigational
BromocriptineBromocriptine may increase the hypertensive and vasoconstricting activities of Etilefrine.Approved, Investigational
BucindololThe risk or severity of adverse effects can be increased when Etilefrine is combined with Bucindolol.Investigational
BunazosinBunazosin may decrease the vasoconstricting activities of Etilefrine.Investigational
CabergolineCabergoline may increase the hypertensive and vasoconstricting activities of Etilefrine.Approved
CarvedilolThe therapeutic efficacy of Etilefrine can be decreased when used in combination with Carvedilol.Approved, Investigational
CeliprololThe risk or severity of adverse effects can be increased when Celiprolol is combined with Etilefrine.Approved, Investigational
ChlorphentermineThe risk or severity of adverse effects can be increased when Chlorphentermine is combined with Etilefrine.Illicit, Withdrawn
ChlorpromazineChlorpromazine may decrease the vasoconstricting activities of Etilefrine.Approved, Investigational, Vet Approved
ClenbuterolThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Etilefrine.Approved, Investigational, Vet Approved
ClozapineClozapine may decrease the vasoconstricting activities of Etilefrine.Approved
DapiprazoleDapiprazole may decrease the vasoconstricting activities of Etilefrine.Approved
DesvenlafaxineDesvenlafaxine may increase the tachycardic activities of Etilefrine.Approved, Investigational
DextroamphetamineDextroamphetamine may decrease the vasoconstricting activities of Etilefrine.Approved, Illicit
DihydroergotamineDihydroergotamine may increase the hypertensive and vasoconstricting activities of Etilefrine.Approved, Investigational
DobutamineThe risk or severity of adverse effects can be increased when Dobutamine is combined with Etilefrine.Approved
DopamineThe risk or severity of adverse effects can be increased when Dopamine is combined with Etilefrine.Approved
DoxazosinThe therapeutic efficacy of Etilefrine can be decreased when used in combination with Doxazosin.Approved
DoxepinDoxepin may decrease the vasoconstricting activities of Etilefrine.Approved, Investigational
DoxofyllineThe risk or severity of adverse effects can be increased when Etilefrine is combined with Doxofylline.Approved, Investigational
DronabinolDronabinol may increase the tachycardic activities of Etilefrine.Approved, Illicit
DronedaroneDronedarone may decrease the vasoconstricting activities of Etilefrine.Approved
DroperidolDroperidol may decrease the vasoconstricting activities of Etilefrine.Approved, Vet Approved
DuloxetineDuloxetine may increase the tachycardic activities of Etilefrine.Approved
EpanololThe risk or severity of adverse effects can be increased when Etilefrine is combined with Epanolol.Experimental
EphedrineThe risk or severity of adverse effects can be increased when Ephedrine is combined with Etilefrine.Approved
EpinephrineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Etilefrine.Approved, Vet Approved
Ergoloid mesylateErgoloid mesylate may increase the hypertensive and vasoconstricting activities of Etilefrine.Approved
ErgonovineErgonovine may increase the hypertensive and vasoconstricting activities of Etilefrine.Approved
ErgotamineErgotamine may increase the hypertensive and vasoconstricting activities of Etilefrine.Approved
EscitalopramEscitalopram may decrease the vasoconstricting activities of Etilefrine.Approved, Investigational
FenoterolThe risk or severity of adverse effects can be increased when Fenoterol is combined with Etilefrine.Approved, Investigational
FenozoloneThe risk or severity of adverse effects can be increased when Etilefrine is combined with Fenozolone.Experimental
FlupentixolFlupentixol may decrease the vasoconstricting activities of Etilefrine.Approved, Investigational, Withdrawn
GanciclovirThe risk or severity of adverse effects can be increased when Etilefrine is combined with Ganciclovir.Approved, Investigational
HyaluronidaseHyaluronidase may increase the vasoconstricting activities of Etilefrine.Approved, Investigational
HydroxyamphetamineThe risk or severity of adverse effects can be increased when Etilefrine is combined with Hydroxyamphetamine.Approved
IloperidoneIloperidone may decrease the vasoconstricting activities of Etilefrine.Approved
ImipramineImipramine may decrease the vasoconstricting activities of Etilefrine.Approved
IndoraminIndoramin may decrease the vasoconstricting activities of Etilefrine.Withdrawn
IobenguaneThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Etilefrine.Approved, Investigational
IsoprenalineThe risk or severity of adverse effects can be increased when Isoprenaline is combined with Etilefrine.Approved, Investigational
IsoxsuprineThe risk or severity of adverse effects can be increased when Isoxsuprine is combined with Etilefrine.Approved, Withdrawn
LabetalolThe risk or severity of adverse effects can be increased when Labetalol is combined with Etilefrine.Approved
LevomilnacipranLevomilnacipran may increase the tachycardic activities of Etilefrine.Approved, Investigational
LinezolidLinezolid may increase the hypertensive activities of Etilefrine.Approved, Investigational
LisdexamfetamineLisdexamfetamine may decrease the vasoconstricting activities of Etilefrine.Approved, Investigational
MefenorexThe risk or severity of adverse effects can be increased when Etilefrine is combined with Mefenorex.Experimental
MephentermineThe risk or severity of adverse effects can be increased when Mephentermine is combined with Etilefrine.Approved
MetaraminolThe risk or severity of adverse effects can be increased when Metaraminol is combined with Etilefrine.Approved, Investigational
MethamphetamineThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Etilefrine.Approved, Illicit
MethotrimeprazineMethotrimeprazine may decrease the vasoconstricting activities of Etilefrine.Approved, Investigational
MethoxamineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Etilefrine.Approved, Investigational
MethylergometrineMethylergometrine may increase the hypertensive and vasoconstricting activities of Etilefrine.Approved
MidodrineThe risk or severity of adverse effects can be increased when Midodrine is combined with Etilefrine.Approved
MilnacipranMilnacipran may increase the tachycardic activities of Etilefrine.Approved, Investigational
NabiloneNabilone may increase the tachycardic activities of Etilefrine.Approved, Investigational
NefazodoneNefazodone may decrease the vasoconstricting activities of Etilefrine.Approved, Withdrawn
NicardipineNicardipine may decrease the vasoconstricting activities of Etilefrine.Approved, Investigational
NicergolineNicergoline may decrease the vasoconstricting activities of Etilefrine.Approved, Investigational
NiguldipineNiguldipine may decrease the vasoconstricting activities of Etilefrine.Experimental
NorepinephrineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Etilefrine.Approved
NortriptylineNortriptyline may decrease the vasoconstricting activities of Etilefrine.Approved
NylidrinThe risk or severity of adverse effects can be increased when Nylidrin is combined with Etilefrine.Approved
OlanzapineOlanzapine may decrease the vasoconstricting activities of Etilefrine.Approved, Investigational
OrciprenalineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Etilefrine.Approved
OxymetazolineThe risk or severity of adverse effects can be increased when Oxymetazoline is combined with Etilefrine.Approved, Investigational
PaliperidonePaliperidone may decrease the vasoconstricting activities of Etilefrine.Approved
Patent BlueThe therapeutic efficacy of Etilefrine can be decreased when used in combination with Patent Blue.Approved
PhenmetrazineThe risk or severity of adverse effects can be increased when Phenmetrazine is combined with Etilefrine.Approved, Illicit
PhenoxybenzaminePhenoxybenzamine may decrease the vasoconstricting activities of Etilefrine.Approved
PhentermineThe risk or severity of adverse effects can be increased when Phentermine is combined with Etilefrine.Approved, Illicit
PhentolaminePhentolamine may decrease the vasoconstricting activities of Etilefrine.Approved
PhenylephrineThe risk or severity of adverse effects can be increased when Phenylephrine is combined with Etilefrine.Approved
PhenylpropanolamineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Etilefrine.Approved, Vet Approved, Withdrawn
PizotifenPizotifen may decrease the vasoconstricting activities of Etilefrine.Approved
PrazosinPrazosin may decrease the vasoconstricting activities of Etilefrine.Approved
PrenalterolThe risk or severity of adverse effects can be increased when Etilefrine is combined with Prenalterol.Experimental
ProcaterolThe risk or severity of adverse effects can be increased when Procaterol is combined with Etilefrine.Approved, Investigational
PromazinePromazine may decrease the vasoconstricting activities of Etilefrine.Approved, Vet Approved
PropericiazinePropericiazine may decrease the vasoconstricting activities of Etilefrine.Approved, Investigational
PropiomazinePropiomazine may decrease the vasoconstricting activities of Etilefrine.Approved
PropiverinePropiverine may decrease the vasoconstricting activities of Etilefrine.Approved, Investigational
PseudoephedrineThe risk or severity of adverse effects can be increased when Etilefrine is combined with Pseudoephedrine.Approved
QuetiapineQuetiapine may decrease the vasoconstricting activities of Etilefrine.Approved
QuinidineQuinidine may decrease the vasoconstricting activities of Etilefrine.Approved, Investigational
RacepinephrineThe risk or severity of adverse effects can be increased when Etilefrine is combined with Racepinephrine.Approved
RisperidoneRisperidone may decrease the vasoconstricting activities of Etilefrine.Approved, Investigational
RitodrineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Etilefrine.Approved, Investigational
SilodosinSilodosin may decrease the vasoconstricting activities of Etilefrine.Approved
SpironolactoneSpironolactone may decrease the vasoconstricting activities of Etilefrine.Approved
SynephrineThe risk or severity of adverse effects can be increased when Etilefrine is combined with Synephrine.Experimental
TamsulosinTamsulosin may decrease the vasoconstricting activities of Etilefrine.Approved, Investigational
Tedizolid phosphateTedizolid Phosphate may increase the hypertensive activities of Etilefrine.Approved
TerazosinTerazosin may decrease the vasoconstricting activities of Etilefrine.Approved
TerbutalineThe risk or severity of adverse effects can be increased when Terbutaline is combined with Etilefrine.Approved
TetryzolineThe risk or severity of adverse effects can be increased when Tetryzoline is combined with Etilefrine.Approved
ThioproperazineThioproperazine may decrease the vasoconstricting activities of Etilefrine.Approved
ThioridazineThioridazine may decrease the vasoconstricting activities of Etilefrine.Approved, Withdrawn
TolazolineTolazoline may decrease the vasoconstricting activities of Etilefrine.Approved, Vet Approved
TramazolineThe risk or severity of adverse effects can be increased when Etilefrine is combined with Tramazoline.Investigational
TrazodoneTrazodone may decrease the vasoconstricting activities of Etilefrine.Approved, Investigational
TretoquinolThe risk or severity of adverse effects can be increased when Etilefrine is combined with Tretoquinol.Experimental
TrifluoperazineTrifluoperazine may decrease the vasoconstricting activities of Etilefrine.Approved, Investigational
TrimazosinTrimazosin may decrease the vasoconstricting activities of Etilefrine.Experimental
TrimipramineTrimipramine may decrease the vasoconstricting activities of Etilefrine.Approved
TyramineThe risk or severity of adverse effects can be increased when Tyramine is combined with Etilefrine.Investigational, Nutraceutical
UrapidilUrapidil may decrease the vasoconstricting activities of Etilefrine.Investigational
VenlafaxineVenlafaxine may increase the tachycardic activities of Etilefrine.Approved
VerapamilVerapamil may decrease the vasoconstricting activities of Etilefrine.Approved
ZiprasidoneZiprasidone may decrease the vasoconstricting activities of Etilefrine.Approved
ZuclopenthixolZuclopenthixol may decrease the vasoconstricting activities of Etilefrine.Approved, Investigational
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
C01CA01 — EtilefrineC01CA51 — Etilefrine, combinations

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2RecruitingTreatmentFlu caused by Influenza1

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 August 02, 2018 06:12