Etilefrine

Identification

Summary

Etilefrine is an adrenergic agonist primarily of α1 and β1 receptors used as an anti-hypotensive.

Generic Name
Etilefrine
DrugBank Accession Number
DB08985
Background

Etilefrine is an adrenergic agonist that appears to interact with beta-1 and some alpha-adrenergic receptors. It has been used as a vasoconstrictor agent.

Type
Small Molecule
Groups
Approved, Withdrawn
Structure
Weight
Average: 181.2316
Monoisotopic: 181.110278729
Chemical Formula
C10H15NO2
Synonyms
  • Etilefrina
  • Etilefrine
  • Etilefrinum
External IDs
  • S 40032
  • S 40032-7

Pharmacology

Indication

Not Available

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofOrthostatic hypotension•••••••••••••••••••••• ••••••••• •••••••• • •••••• ••••••
Contraindications & Blackbox Warnings
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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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcebutololThe therapeutic efficacy of Etilefrine can be decreased when used in combination with Acebutolol.
AceclofenacThe risk or severity of hypertension can be increased when Aceclofenac is combined with Etilefrine.
AcemetacinThe risk or severity of hypertension can be increased when Etilefrine is combined with Acemetacin.
Acetylsalicylic acidThe risk or severity of hypertension can be increased when Acetylsalicylic acid is combined with Etilefrine.
AclidiniumThe risk or severity of Tachycardia can be increased when Aclidinium is combined with Etilefrine.
Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Etilefrine hydrochlorideZBI6Q5FH3S943-17-9KTNROWWHOBZQGK-UHFFFAOYSA-N
International/Other Brands
Apocretin / Circupon / Effontil / Effortil / Effortilvet / Eti-Puren / Kertasin / Phetanol / Phetasin / Tonus-Forte / Updormin

Categories

ATC Codes
C01CA51 — Etilefrine, combinationsC01CA01 — Etilefrine
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
1,2-aminoalcohol / 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Alcohol / Amine / Aralkylamine / Aromatic alcohol / Aromatic homomonocyclic compound / Hydrocarbon derivative / Monocyclic benzene moiety
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
ZB6F8MY53V
CAS number
709-55-7
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=CC(O)=C1

References

Synthesis Reference

British Patent 1,358,973.

General References
Not Available
KEGG Drug
D07931
PubChem Compound
3306
PubChem Substance
310264946
ChemSpider
3190
BindingDB
97154
RxNav
4169
ChEBI
91518
ChEMBL
CHEMBL86882
Wikipedia
Etilefrine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentHepatic Ascites1
Not AvailableRecruitingTreatmentBlood Pressures / Intra-operative Hypotension / Postoperative Complications1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
SolutionOral0.750 g
TabletOral5.000 mg
SolutionOral5 mg/mL
Capsule, extended release25 MG
Injection, solutionIntramuscular; Subcutaneous10 MG/1ML
Injection, solutionIntramuscular; Subcutaneous15 mg/ml
SolutionOral7.5 mg/mL
Solution / dropsOral
Solution / dropsOral7.5 MG/ML
TabletOral
TabletOral5 mg/1
Injection, solutionIntramuscular; Intravenous; Subcutaneous10 mg
SolutionOral7.5 mg
SolutionIntramuscular; Intravenous; Subcutaneous10 mg
Tablet, coatedOral5 mg
TabletOral5 mg
Tablet, sugar coatedOral5 mg
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
Polarizability20.33 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-MSsplash10-0a4i-9200000000-095e0ad872f2de257b08
MS/MS Spectrum - , positiveLC-MS/MSsplash10-05no-3900000000-dc75520c0fb8e17d3ef6
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-01q9-2900000000-f6138f762d8e688d153e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-6900000000-503326779d4cf56fa250
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0601-3900000000-ac0c8a7257bedc8e334e
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kf-6900000000-c3484ed5db819946291f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014l-9800000000-bb0153d8f6b5ac9f80e5
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kf-7900000000-1f005d189aa6de3728a6
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-136.75725
predicted
DeepCCS 1.0 (2019)
[M+H]+140.43416
predicted
DeepCCS 1.0 (2019)
[M+Na]+149.73622
predicted
DeepCCS 1.0 (2019)

Drug created at June 10, 2014 17:55 / Updated at June 02, 2021 20:03