NAV

Etafedrine

Identification

Summary

Etafedrine is a beta-2 adrenoceptor agonist used to treat a cough associated with inflamed mucosa.

Brand Names
Dalmacol
Generic Name
Etafedrine
DrugBank Accession Number
DB11587
Background

Etafedrine (INN) or ethylephedrine is a long-acting bronchodilator and has been an ingredient combined with other drugs in the brand names Nethaprin 3 and Dalmacol 10. It was previously available as both the free base and as the hydrochloride salt manufactured by Sanofi-Aventis (now Sanofi) has been discontinued 7.

Ethylephedrine is be formed by alkylating ephedrine with ethyl iodide. The hydrochloride is be prepared by passing hydrogen chloride through a solution of ethylephedrine in diethyl ether 11.

This belongs to the family of medications called decongestants. It acts by narrowing blood vessels in the nasal passages, helping to relieve nasal congestion 11.

Type
Small Molecule
Groups
Approved
Structure
3D
Similar Structures
Weight
Average: 193.29
Monoisotopic: 193.146664236
Chemical Formula
C12H19NO
Synonyms
  • (-)-etafedrine
  • alpha-(1-(ethylmethylamino)ethyl)benzyl alcohol
  • Etafedrine
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Pharmacology

Indication

Conditions characterized by bronchial congestion and bronchospasm when an expectorant or bronchodilator action is required, such as acute bronchitis, acute episodes of chronic bronchitis and bronchial asthma 8, 9.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to preventAsthmaCombination Product in combination with: Theophylline (DB00277), Guaifenesin (DB00874)••••••••••••••••••
Used in combination to treatAsthmaCombination Product in combination with: Guaifenesin (DB00874), Theophylline (DB00277)••••••••••••••••••
Used in combination to treatBronchospasmCombination Product in combination with: Theophylline (DB00277), Guaifenesin (DB00874)••••••••••••••••••
Symptomatic treatment ofBronchospasm••••••••••••
Used in combination to treatChronic bronchitisCombination Product in combination with: Theophylline (DB00277), Guaifenesin (DB00874)••••••••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Etafedrine helps to control the cough which is associated with irritation of the mouth and throat that is not alleviated by cough medications that are less strong 7.

The results of one study in 48 individuals showed that lung FEV1 (forced expiratory volume) and lung VC (vital capacity) were significantly improved with etafedrine, sleep improved, and patients showed improved appetite in addition to the suppression of cough 3.

Mechanism of action

A sympathomimetic agent, etafedrine acts on the sympathetic receptors of the bronchial tree, relieving spasm in a manner similar to that of ephedrine 6.

Etafedrine acts as a selective β adrenoreceptor agonist, thereby mediating its bronchodilator effects without increasing norepinephrine release 7. This is distinctly different from ephedrine and tyramine which trigger the release of epinephrine or norepinephrine.

N-ethylation of ephedrine suppresses the indirect sympathomimetic activity and markedly enhances the efficacy on beta 2- adrenoceptors 11.

TargetActionsOrganism
ABeta-2 adrenergic receptor
agonist
Humans
Absorption

Similar to its parent drug, ephedrine, it is readily and completely absorbed from the gastrointestinal tract; plasma peak concentrations are reached an hour after ingestion 9.

A single oral dose of 24 mg produced an average peak plasma concentration of 0.10 mg/L 9.

Volume of distribution

Similar to ephedrine, at about 3L/kg 9.

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Excreted mainly in the urine 9.

Half-life

It has a plasma half-life ranging from 3 to 6 hours depending on urinary pH 9.

Clearance

Not Available

Adverse Effects
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Toxicity

This drug is a sympathomimetic, and therefore has the following adverse effects (in parallel with ephedrine) 8: tremor, fear, anxiety, confusion, irritability, insomnia, and psychotic states. Paranoid psychosis, delusions, and hallucinations may also follow overdose 9.

The adverse effects of ephedrine and similar drugs are believed to be related to coronary artery constriction, vasospasm, shortening of cardiac refractory periods allowing re-entrant cardiac arrhythmias, hypertension-induced subarachnoid hemorrhage, cerebral artery vasoconstriction as well as sympathomimetic-induced platelet activation 8.

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
Integrate drug-drug
interactions in your software
AbacavirAbacavir may decrease the excretion rate of Etafedrine which could result in a higher serum level.
AcebutololThe therapeutic efficacy of Etafedrine can be decreased when used in combination with Acebutolol.
AceclofenacThe risk or severity of hypertension can be increased when Aceclofenac is combined with Etafedrine.
AcemetacinThe risk or severity of hypertension can be increased when Etafedrine is combined with Acemetacin.
AcetaminophenAcetaminophen may decrease the excretion rate of Etafedrine which could result in a higher serum level.
Food Interactions
  • Take with a full glass of water.
  • Take with or without food.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Etafedrine hydrochlorideY134VQ304Y530-35-8WRONACHIHQGZSD-JGAZGGJJSA-N
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
DalmacolEtafedrine hydrochloride (16.65 mg / 5 mL) + Doxylamine succinate (6 mg / 5 mL) + Ethanol (0.25 mL / 5 mL) + Hydrocodone bitartrate (1.65 mg / 5 mL) + Sodium citrate (200 mg / 5 mL)SyrupOralLaboratoire Atlas Inc1983-12-31Not applicableCanada flag
DalmacolEtafedrine hydrochloride (16.65 mg / 5 mL) + Doxylamine succinate (6 mg / 5 mL) + Ethanol (0.25 mL / 5 mL) + Hydrocodone bitartrate (1.65 mg / 5 mL) + Sodium citrate (200 mg / 5 mL)SyrupOralLaboratoire Riva Inc.1997-03-26Not applicableCanada flag
Mercodol With DecaprynEtafedrine hydrochloride (16.65 mg / 5 mL) + Doxylamine succinate (6 mg / 5 mL) + Hydrocodone bitartrate (1.65 mg / 5 mL) + Sodium citrate (200 mg / 5 mL)SyrupOralAventis Pharma Ltd.1994-12-312001-07-20Canada flag
Ratio-calmydoneEtafedrine hydrochloride (3.33 mg / mL) + Doxylamine succinate (1.2 mg / mL) + Hydrocodone bitartrate (0.33 mg / mL) + Sodium citrate (40 mg / mL)SyrupOralTEVA Canada Limited1981-12-312017-04-04Canada flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenylpropanes
Direct Parent
Phenylpropanes
Alternative Parents
Aralkylamines / Trialkylamines / Secondary alcohols / 1,2-aminoalcohols / Organopnictogen compounds / Hydrocarbon derivatives / Aromatic alcohols
Substituents
1,2-aminoalcohol / Alcohol / Amine / Aralkylamine / Aromatic alcohol / Aromatic homomonocyclic compound / Hydrocarbon derivative / Organic nitrogen compound / Organic oxygen compound / Organonitrogen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans

Chemical Identifiers

UNII
2Y6VQU63E8
CAS number
48141-64-6
InChI Key
IRVLBORJKFZWMI-JQWIXIFHSA-N
InChI
InChI=1S/C12H19NO/c1-4-13(3)10(2)12(14)11-8-6-5-7-9-11/h5-10,12,14H,4H2,1-3H3/t10-,12-/m0/s1
IUPAC Name
(1R,2S)-2-[ethyl(methyl)amino]-1-phenylpropan-1-ol
SMILES
CCN(C)[C@@H](C)[C@H](O)C1=CC=CC=C1

References

General References
  1. Lindmar R, Loffelholz K, Stieh-Koch U: On the mechanism of bronchodilatation by etafedrine. Arzneimittelforschung. 1985;35(3):602-4. [Article]
  2. ASTROM A: Pharmacological actions of 1-N-ethyl ephedrine and 1-ephedrine; a quantitative comparison. Acta Pharmacol Toxicol (Copenh). 1948;4(1):53-64. [Article]
  3. Kagan G, Rose R: Double-blind trial of a long-acting bronchodilator preparation ("Nethaprin Dospan") in bronchospastic disease. Curr Med Res Opin. 1976;4(6):436-41. doi: 10.1185/03007997609112000 . [Article]
  4. Wooltorton E, Sibbald B: Ephedra/ephedrine: cardiovascular and CNS effects. CMAJ. 2002 Mar 5;166(5):633. [Article]
  5. https://pubchem.ncbi.nlm.nih.gov/compound/etafedrine [Link]
  6. SA Drug label, Nethaprin [Link]
  7. Etafedrine [Link]
  8. Ephedrine [Link]
  9. Ephedrine [Link]
  10. Dalmacol [Link]
  11. Etafedrine Hydrochloride [File]
ChemSpider
85308
ZINC
ZINC000001846418
Wikipedia
Etafedrine
MSDS
Download (496 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
SyrupOral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)108-110MSDS
Predicted Properties
PropertyValueSource
Water Solubility9.44 mg/mLALOGPS
logP2.07ALOGPS
logP2.06Chemaxon
logS-1.3ALOGPS
pKa (Strongest Acidic)13.88Chemaxon
pKa (Strongest Basic)9.14Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area23.47 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity59.73 m3·mol-1Chemaxon
Polarizability22.83 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
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-MSsplash10-0a4r-9300000000-a905b1eea404e13f7240
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-004r-5900000000-8e682038ce05ff314216
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-1900000000-66681d594aed48c66bce
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014r-9600000000-943e08ad0974d25397ad
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-3900000000-60f75f4d92c5405c7a1d
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00r6-9300000000-7bda3990900d7b51c64a
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-056r-9400000000-50fb09d28563e9052f29
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]-149.2848
predicted
DeepCCS 1.0 (2019)
[M+H]+151.68037
predicted
DeepCCS 1.0 (2019)
[M+Na]+157.5951
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Beta-2 adrenergic receptor
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Protein homodimerization activity
Specific Function
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately ...
Gene Name
ADRB2
Uniprot ID
P07550
Uniprot Name
Beta-2 adrenergic receptor
Molecular Weight
46458.32 Da
References
  1. Etafedrine [Link]
  2. Etafedrine Hydrochloride [File]

Drug created at April 27, 2016 23:42 / Updated at February 21, 2021 18:53