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
Structure for Etafedrine (DB11587)
- Weight
- Average: 193.29
Monoisotopic: 193.146664236 - Chemical Formula
- C12H19NO
- Synonyms
- (-)-etafedrine
- alpha-(1-(ethylmethylamino)ethyl)benzyl alcohol
- Etafedrine
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.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to prevent Asthma Combination Product in combination with: Theophylline (DB00277), Guaifenesin (DB00874) •••••••••••• •••••• Used in combination to treat Asthma Combination Product in combination with: Guaifenesin (DB00874), Theophylline (DB00277) •••••••••••• •••••• Used in combination to treat Bronchospasm Combination Product in combination with: Theophylline (DB00277), Guaifenesin (DB00874) •••••••••••• •••••• Symptomatic treatment of Bronchospasm •••••••••••• Used in combination to treat Chronic bronchitis Combination Product in combination with: Theophylline (DB00277), Guaifenesin (DB00874) •••••••••••• •••••• - Contraindications & Blackbox Warnings
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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.
Target Actions Organism ABeta-2 adrenergic receptor agonistHumans - 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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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 Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Abacavir may decrease the excretion rate of Etafedrine which could result in a higher serum level. Acebutolol The therapeutic efficacy of Etafedrine can be decreased when used in combination with Acebutolol. Aceclofenac The risk or severity of hypertension can be increased when Aceclofenac is combined with Etafedrine. Acemetacin The risk or severity of hypertension can be increased when Etafedrine is combined with Acemetacin. Acetaminophen Acetaminophen 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
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Etafedrine hydrochloride Y134VQ304Y 530-35-8 WRONACHIHQGZSD-JGAZGGJJSA-N - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Dalmacol Etafedrine 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) Syrup Oral Laboratoire Atlas Inc 1983-12-31 Not applicable Canada 
Dalmacol Etafedrine 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) Syrup Oral Laboratoire Riva Inc. 1997-03-26 Not applicable Canada Mercodol With Decapryn Etafedrine 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) Syrup Oral Aventis Pharma Ltd. 1994-12-31 2001-07-20 Canada Ratio-calmydone Etafedrine hydrochloride (3.33 mg / mL) + Doxylamine succinate (1.2 mg / mL) + Hydrocodone bitartrate (0.33 mg / mL) + Sodium citrate (40 mg / mL) Syrup Oral TEVA Canada Limited 1981-12-31 2017-04-04 Canada
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
- Lindmar R, Loffelholz K, Stieh-Koch U: On the mechanism of bronchodilatation by etafedrine. Arzneimittelforschung. 1985;35(3):602-4. [Article]
- 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]
- 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]
- Wooltorton E, Sibbald B: Ephedra/ephedrine: cardiovascular and CNS effects. CMAJ. 2002 Mar 5;166(5):633. [Article]
- https://pubchem.ncbi.nlm.nih.gov/compound/etafedrine [Link]
- SA Drug label, Nethaprin [Link]
- Etafedrine [Link]
- Ephedrine [Link]
- Ephedrine [Link]
- Dalmacol [Link]
- Etafedrine Hydrochloride [File]
- External Links
- ChemSpider
- 85308
- ZINC
- ZINC000001846418
- Wikipedia
- Etafedrine
- MSDS
- Download (496 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Syrup Oral - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 108-110 MSDS - Predicted Properties
Property Value Source Water Solubility 9.44 mg/mL ALOGPS logP 2.07 ALOGPS logP 2.06 Chemaxon logS -1.3 ALOGPS pKa (Strongest Acidic) 13.88 Chemaxon pKa (Strongest Basic) 9.14 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 23.47 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 59.73 m3·mol-1 Chemaxon Polarizability 22.83 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0a4r-9300000000-a905b1eea404e13f7240 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-004r-5900000000-8e682038ce05ff314216 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-1900000000-66681d594aed48c66bce Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-014r-9600000000-943e08ad0974d25397ad Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-014i-3900000000-60f75f4d92c5405c7a1d Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-00r6-9300000000-7bda3990900d7b51c64a Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-056r-9400000000-50fb09d28563e9052f29 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 149.2848 predictedDeepCCS 1.0 (2019) [M+H]+ 151.68037 predictedDeepCCS 1.0 (2019) [M+Na]+ 157.5951 predictedDeepCCS 1.0 (2019)
Targets
- 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
Drug created at April 27, 2016 23:42 / Updated at February 21, 2021 18:53