Page last updated: 2024-12-05

etilefrine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Etilefrine: A phenylephrine-related beta-1 adrenergic and alpha adrenergic agonist used as a cardiotonic and antihypotensive agent. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID3306
CHEMBL ID86882
CHEBI ID91518
SCHEMBL ID150802
MeSH IDM0007916

Synonyms (109)

Synonym
corcanfol
ethylefrine
CHEMBL86882
dl-etilefrin
s-40032
s-40032-7
ec 211-910-4
etilefrin dl-form
einecs 233-359-9
etilefrine [inn:ban]
etilefrinum
etilefrina
unii-zb6f8my53v
(1)-alpha-((ethylamino)methyl)-m-hydroxybenzyl alcohol
zb6f8my53v ,
BRD-A09925278-003-03-1
etilefrine
benzenemethanol, .alpha.-[(ethylamino)methyl]-3-hydroxy-
BSPBIO_001173
ENAMINE_002760
3-[2-(ethylamino)-1-hydroxyethyl]phenol
etilefrinum [latin]
etilephrine
(+-)-etilefrine
benzenemethanol, alpha-((ethylamino)methyl)-3-hydroxy-
s 40032-7
etilefrina [spanish]
etilefrinum [inn-latin]
m-hydroxy-alpha-(ethylaminomethyl)benzyl alcohol
1-(3-hydroxyphenyl)-2-(ethylamino)ethanol
ethyladrianol
m-hydroxyphenylethanolethylamine
etilefrin
alpha-(m-hydroxyphenyl)-beta-(ethylamino)ethanol
s 40032
(+-)-etilefrin
alpha-((ethylamino)methyl)-m-hydroxybenzyl alcohol
einecs 211-910-4
ethylphenylephrine
racemic etilefrine
etilefrina [dcit]
benzyl alcohol, alpha-((ethylamino)methyl)-m-hydroxy-
1-(3'-hydroxyphenyl)-2-ethylaminoethanol
n-ethylnorphenylephrine
ethyl noradrianol
etilefrine [inn]
NCGC00179276-01
PRESTWICK2_001017
OPREA1_593945
IDI1_007107
benzenemethanol, .alpha-[(ethylamino)methyl]-3-hydroxy-, hydrochloride
effortil
3-[2-(ethylamino)-1-hydroxy-ethyl]phenol
709-55-7
.alpha.-[(ethylamino)methyl]-3-hydroxybenzenemethanol hydrochloride
AB00514701
PRESTWICK1_001017
SPBIO_003044
PRESTWICK0_001017
BPBIO1_001291
PRESTWICK3_001017
smr000685797
MLS000881153 ,
AKOS000116366
HMS1401N10
D07931
corcanfol (tn)
etilefrine (inn)
HMS2233J17
BBL027207
STL377784
niosh/do5600010
(+-)-alpha-((ethylamino)methyl)-m-hydroxybenzyl alcohol
(+-)-ethylephrine
r,s-ethylephrine
benzyl alcohol, alpha-((ethylamino)methyl)-m-hydroxy-, (+-)
DO56000100
cid_3306
bdbm97154
3-[2-(ethylamino)-1-oxidanyl-ethyl]phenol
HMS3370K09
AB00514701-08
AKOS022060703
SCHEMBL150802
benzenemethanol, .alpha.-((ethylamino)methyl)-3-hydroxy-
etilefrine [who-dd]
etilefrin [mi]
.alpha.-(m-hydroxyphenyl)-.beta.-(ethylamino)ethanol
benzyl alcohol, .alpha.-((ethylamino)methyl)-m-hydroxy-
.alpha.-((ethylamino)methyl)-m-hydroxybenzyl alcohol
10128-36-6
(+/-)-etilefrine
SQVIAVUSQAWMKL-UHFFFAOYSA-N
3-[2-(ethylamino)-1-hydroxyethyl]phenol #
etiladrianol
(.+/-.)-etilefrin
(.+/-.)-etilefrine
NCGC00179276-04
DTXSID1023029
DB08985
CHEBI:91518
Z56836691
Q417873
BRD-A09925278-001-07-6
EN300-33921
etilefrine-d5
709-55-7 (free base)
HY-A0144
CS-0017466

Research Excerpts

Overview

Etilefrine is a sympathomimetic amine with high affinity for alpha- and beta2-receptors. It is believed to be a safe and low cost alternative to other alpha-adrenergic agents in the prevention of drug-induced priapism.

ExcerptReferenceRelevance
"Etilefrine is a sympathomimetic amine with high affinity for alpha- and beta2-receptors. "( The effect of etilefrine (Effortil) on regional blood flow during arterial reconstructive surgery.
Ekeström, S; Liljeqvist, L; Nordhus, O, 1980
)
2.06
"Etilefrine is believed to be a safe and low cost alternative to other alpha-adrenergic agents in the prevention of drug-induced priapism."( [Prevention of prolonged drug-induced erection by intracavernous injection of etilefrine].
Fiter Gómez, L; Gimeno Albo, F; Herrero Payo, A; Mejías Callaved, J, 1997
)
1.25
"Etilefrine is an alpha-agonist agent with a potent vasoconstrictor effect, which is potentially useful in preventing vasovagal syncope by reducing venous pooling and/or by counteracting reflex arteriolar vasodilatation. "( Effect of etilefrine in preventing syncopal recurrence in patients with vasovagal syncope: a double-blind, randomized, placebo-controlled trial. The Vasovagal Syncope International Study.
Alboni, P; Brignole, M; Giani, P; Menozzi, C; Moya, A; Raviele, A; Sutton, R, 1999
)
2.15

Actions

Etilefrine proved to cause a significant increase of cardiac output (QPA), mean systemic blood pressure and aorto-coronary bypass flow. The increase in cardiac output and the reduction in TPR are mediated through beta-adrenoceptors.

ExcerptReferenceRelevance
"With etilefrine, the increase in cardiac output and the reduction in TPR are mediated through beta-adrenoceptors while the increases in RHFP, blood pressure and TPR are a direct action on the alpha-adrenoceptors."( A comparison of the effects of salbutamol, etilefrine and dextran during hypotension and low cardiac output states in rabbit.
Adigun, SA; Fentem, PH,
)
0.85
"Etilefrine proved to cause a significant increase of cardiac output (QPA), mean systemic blood pressure and aorto-coronary bypass flow."( The effect of etilefrine (Effortil) on central hemodynamics and aorto-coronary bypass blood flow. A pre-operative study.
Ekeström, S; Liljeqvist, L; Lothigius, B; Nordhus, O, 1979
)
1.34

Pharmacokinetics

ExcerptReferenceRelevance
" pharmacokinetic data on 670 drugs representing, to our knowledge, the largest publicly available set of human clinical pharmacokinetic data."( Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
Lombardo, F; Obach, RS; Waters, NJ, 2008
)
0.35

Bioavailability

The relative bioavailability of a prodrug of etilefrine, its stearic acid ester, was determined by means of plasma levels and renal excretion. A meanBioavailability of 70 and 58 per cent (Thomasin) or of 78 and 108 per cent(Thomasin retard) was calculated by comparison of the corresponding AUC- and CUE-values.

ExcerptReferenceRelevance
" A mean bioavailability of 70 and 58 per cent (Thomasin) or of 78 and 108 per cent (Thomasin retard) was calculated by comparison of the corresponding AUC- and CUE-values of the total etilefrine."( [Bioavailability of etilefrine from Thomasin and Thomasin sustained-release tablets].
Haustein, KO; Hüller, G, 1985
)
0.78
"The relative bioavailability of a prodrug of etilefrine, its stearic acid ester, was determined by means of plasma levels and renal excretion."( Pharmacokinetic comparison of etilefrine to its prodrug, the stearic acid ester of etilefrine.
Hitzenberger, G; Rominger, KL, 1980
)
0.81
" In six volunteers bioavailability was reduced to 35% for a fast release tablet and to 17% for a sustained release preparation."( Dihydroergotamine increases the bioavailability of orally administered etilefrine.
Dengler, HJ; Hengstmann, JH; Hengstmann, R; Schwonzen, S, 1982
)
0.5
"The quantitative structure-bioavailability relationship of 232 structurally diverse drugs was studied to evaluate the feasibility of constructing a predictive model for the human oral bioavailability of prospective new medicinal agents."( QSAR model for drug human oral bioavailability.
Topliss, JG; Yoshida, F, 2000
)
0.31
"Oral bioavailability (F) is a product of fraction absorbed (Fa), fraction escaping gut-wall elimination (Fg), and fraction escaping hepatic elimination (Fh)."( Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.
Chang, G; El-Kattan, A; Miller, HR; Obach, RS; Rotter, C; Steyn, SJ; Troutman, MD; Varma, MV, 2010
)
0.36
" Buccal application at open conditions for 1 h exhibited absolute bioavailability of more than 20%, while the intragastric administration gave much lower bioavailability (<10%)."( Absorption behavior of etilefrine after buccal administration in rats.
Onishi, H; Sakata, O, 2018
)
0.79

Dosage Studied

In 40 hypotensive patients with sympathicotonic orthostatic dysregulation, a dosage of 3 times daily 2 mg dihydroergotamine or 20 mg etilefrine or the fixed combination of both drugs--Dihydergot plus--was compared.

ExcerptRelevanceReference
" Cocaine or phentolamine shifted the dose-response curve to the left."( Effects of ethylephrine on the rat atrial pacemaker.
Aramendía, P; De Mikulic, LE; Márquez, MT, 1977
)
0.26
" In a preceding dose finding study equipotent dosage of the substances used was confirmed."( [Hemodynamic effects following bolus administration of different vasopressive agents for blood pressure stabilization during peridural anesthesia].
Boldt, J; Börner, U; Brähler, A; Hempelmann, G; Müller, H; Stoyanov, M, 1985
)
0.27
"In 40 hypotensive patients with sympathicotonic orthostatic dysregulation and presenting the relevant subjective symptoms, a dosage of 3 times daily 2 mg dihydroergotamine or 20 mg etilefrine or the fixed combination of both drugs--Dihydergot plus--was compared inter-individually and by the double blind method."( [Treatment of hypotensive circulatory dysregulation with a combination of dihydroergotamine and etilefrine (author's transl)].
Bracharz, H; Polzien, P, 1981
)
0.67
" Results of analysis of pure drugs and their dosage forms by the proposed method were in good agreement with either a reported derivative spectrophotometric procedure or the USP XXII method for etilefrine hydrochloride and ritodrine hydrochloride, respectively."( Spectrophotometric determination of etilefrine hydrochloride and ritodrine hydrochloride through nitrosation and subsequent cobalt chelation.
Bakry, RS; Belal, SF; el Walily, AM, 1995
)
0.76
"In the 20 participating centers, 126 patients with recurrent vasovagal syncope (at least 3 episodes in the last 2 years) and a positive baseline head-up tilt response were randomly assigned to placebo (63 patients) or etilefrine at a dosage of 75 mg/d (63 patients) and were followed up for 1 year or until syncope recurred."( Effect of etilefrine in preventing syncopal recurrence in patients with vasovagal syncope: a double-blind, randomized, placebo-controlled trial. The Vasovagal Syncope International Study.
Alboni, P; Brignole, M; Giani, P; Menozzi, C; Moya, A; Raviele, A; Sutton, R, 1999
)
0.89
" The method was applied successfully in determining the drugs in dosage forms and in biological fluids."( Determination of phenolic sympathomimetic drugs in pharmaceutical samples and biological fluids by flow-injection chemiluminescence.
Al-Tamimi, SA; Alwarthan, AA; Aly, FA,
)
0.13
"A new, simple, sensitive and rapid spectrofluorimetric method has been developed for determination of certain adrenergic agonists such as isoxsuprine hydrochloride, ritodrine hydrochloride and etilefrine hydrochloride in their pure forms and pharmaceutical dosage forms."( Spectrofluorimetric determination of certain adrenergic agonist drugs in their pure forms and pharmaceutical formulations: Content uniformity test application.
Attia, TZ; Badr El-Din, KM, 2017
)
0.64
" Dosage forms of orally administered tablets and parenteral injections are clinically available, but exhibit unfavorable characteristics, including cardiac toxicity, headaches, and damage at the injection site for the parenteral dosage form, and initially high plasma levels, fast elimination, and first-pass effects for its oral administration."( Absorption behavior of etilefrine after buccal administration in rats.
Onishi, H; Sakata, O, 2018
)
0.79
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
phenolsOrganic aromatic compounds having one or more hydroxy groups attached to a benzene or other arene ring.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (4)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
gemininHomo sapiens (human)Potency17.78280.004611.374133.4983AID624297
D(3) dopamine receptor isoform eHomo sapiens (human)Potency7.07950.02009.148539.8107AID720506
Spike glycoproteinSevere acute respiratory syndrome-related coronavirusPotency12.58930.009610.525035.4813AID1479145
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
galanin receptor type 3Homo sapiens (human)IC50 (µMol)1.33100.00661.54317.3650AID687013
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
virion membraneSpike glycoproteinSevere acute respiratory syndrome-related coronavirus
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (36)

Assay IDTitleYearJournalArticle
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral research, Sep, Volume: 91, Issue:3
High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
AID540211Fraction unbound in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID29811Oral bioavailability in human2000Journal of medicinal chemistry, Jun-29, Volume: 43, Issue:13
QSAR model for drug human oral bioavailability.
AID425653Renal clearance in human2009Journal of medicinal chemistry, Aug-13, Volume: 52, Issue:15
Physicochemical determinants of human renal clearance.
AID444053Renal clearance in human2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.
AID26304Partition coefficient (logD6.5)2000Journal of medicinal chemistry, Jun-29, Volume: 43, Issue:13
QSAR model for drug human oral bioavailability.
AID444055Fraction absorbed in human2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.
AID444058Volume of distribution at steady state in human2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.
AID444052Hepatic clearance in human2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.
AID540213Half life in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID444051Total clearance in human2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.
AID540209Volume of distribution at steady state in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID1136412Displacement of (-)-[3H]alprenolol from adrenergic receptor purified from frog erythrocytes1978Journal of medicinal chemistry, Sep, Volume: 21, Issue:9
Structure-activity study of beta-adrenergic agents using the SIMCA method of pattern recognition.
AID444057Fraction escaping hepatic elimination in human2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.
AID22293Delta logD (logD6.5 - logD7.4)2000Journal of medicinal chemistry, Jun-29, Volume: 43, Issue:13
QSAR model for drug human oral bioavailability.
AID444050Fraction unbound in human plasma2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.
AID444056Fraction escaping gut-wall elimination in human2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.
AID29359Ionization constant (pKa)2000Journal of medicinal chemistry, Jun-29, Volume: 43, Issue:13
QSAR model for drug human oral bioavailability.
AID540212Mean residence time in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID425652Total body clearance in human2009Journal of medicinal chemistry, Aug-13, Volume: 52, Issue:15
Physicochemical determinants of human renal clearance.
AID444054Oral bioavailability in human2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.
AID540210Clearance in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (211)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990128 (60.66)18.7374
1990's29 (13.74)18.2507
2000's27 (12.80)29.6817
2010's18 (8.53)24.3611
2020's9 (4.27)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 47.70

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index47.70 (24.57)
Research Supply Index5.61 (2.92)
Research Growth Index4.36 (4.65)
Search Engine Demand Index75.88 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (47.70)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials38 (16.17%)5.53%
Reviews9 (3.83%)6.00%
Case Studies20 (8.51%)4.05%
Observational0 (0.00%)0.25%
Other168 (71.49%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (2)

Trial Overview

TrialPhaseEnrollmentStudy TypeStart DateStatus
HIgh Versus STAndard Blood Pressure Target in Hypertensive High-risk Patients: The HISTAP Randomized Clinical Trial. [NCT05637606]636 participants (Anticipated)Interventional2023-03-06Recruiting
Effects of Adding Hypertonic Saline Solutions and/or Etilefrine to Standard Diuretics Therapy in Egyptian Cirrhotic Patients With Ascites [NCT04785755]Phase 290 participants (Actual)Interventional2017-11-30Completed
[information is prepared from clinicaltrials.gov, extracted Sep-2024]