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| Clinical data | |
|---|---|
| Trade names | Effortil, many others[1][2] |
| Other names | Etilephrine; Ethylnorphenylephrine; Ethylphenephrine; Ethyladrianol; Etiladrianol; Aethyladrianol; M-I-36; 3,β-Dihydroxy-N-ethylphenethylamine; 3,β-Dihydroxy-N-ethyl-β-phenylethylamine |
| AHFS/Drugs.com | International Drug Names |
| Routes of administration | Oral,injection[3][4] |
| Drug class | Adrenergic receptoragonist;Sympathomimetic |
| ATC code | |
| Pharmacokinetic data | |
| Bioavailability | Oral: 50%[3] |
| Protein binding | 23% (8.5% toalbumin)[3] |
| Metabolism | Conjugation (glucuronidation)[3] |
| Metabolites | •Conjugates[3] • Hydroxymandelic acid (3%)[3] |
| Eliminationhalf-life | 2.5 hours[3] |
| Excretion | Urine (80%; 7–28% unchanged, 44–73% asconjugates)[3] |
| Identifiers | |
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| CompTox Dashboard(EPA) | |
| ECHA InfoCard | 100.010.829 |
| Chemical and physical data | |
| Formula | C10H15NO2 |
| Molar mass | 181.235 g·mol−1 |
| 3D model (JSmol) | |
| Chirality | Racemic mixture |
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Etilefrine, sold under the brand nameEffortil among others, is asympathomimeticmedication used as anantihypotensive agent to treatorthostatic hypotension.[1] It is usually usedby mouth, but is also available as aninjectable.[3][4]
Side effects of etilefrine includenausea,tremors, andpalpitations, among others.[5] Etilefrine is anagonist of theα- andβ-adrenergic receptors.[6] It is asubstituted phenethylamine and is related toepinephrine,phenylephrine, andnorfenefrine.[2]
Etilefrine was first described and introduced for medical use by 1949.[7][8]
Etilefrine is used to treatorthostatic hypotension and as anasal decongestant.[5][9] It has also been usedoff-label to treatpriapism.[6][9]
Side effects of etilefrine includenausea,tremors, andpalpitations, among others.[5]
Etilefrine is anagonist of theα1-adrenergic receptor.[5] It is avasoconstrictor andantihypotensive agent.[5] It has also been described as aβ1-adrenergic receptor agonist with some agonistic actions at theα- andβ2-adrenergic receptors.[9]
Intravenous infusion of this compound increasescardiac output,stroke volume,venous return, and blood pressure in humans and animals, suggesting stimulation of both α- andβ-adrenergic receptors.[10][11][12][13][14] However,in vitro studies indicate that etilefrine has a much higher affinity for β1 (cardiac) than for β2adrenoreceptors.[15]
Intravenous etilefrine increases the pulse rate, cardiac output, stroke volume,central venous pressure, andmean arterial pressure of healthy individuals.Peripheral vascular resistance falls during the infusion of 1 to 8 mg etilefrine but begins to rise at higher dosage. Marked falls in pulse rate, cardiac output, stroke volume, and peripheral blood flow, accompanied by rises in mean arterial pressure, occur when etilefrine is infused after administration of intravenouspropranolol 2.5 mg. These findings indicate that etilefrine has both β1- and α1-adrenergic receptor actions in humans.
Etilefrine is rapidlyabsorbed withoral administration.[3] The oralbioavailability of etilefrine is approximately 50%.[3]Peak concentrations of etilefrine occur after 30 minutes.[3]
Theplasma protein binding of etilefrine is 23%.[3] About 8.5% is bound toalbumin.[3]
Etilefrine is aperipherally selective drug.[16]
Etilefrine ismetabolized byconjugation, for instanceglucuronidation, in theliver andgastrointestinal tract.[3] There appears to be significantfirst-pass metabolism.[3] About 3% is metabolized into hydroxymandelic acid.[3]
Theelimination of etilefrine is dependent onroute of administration.[3] Regardless of route, about 80% isexcreted inurine within 24 hours.[3] With oral administration, 7% is eliminated unchanged in urine and 73% as conjugates.[3] Conversely, with intravenous administration, 28% is eliminated unchanged in urine and 44% as conjugates.[3]
Etilefrine, also known as 3,β-dihydroxy-N-ethylphenethylamine, is asubstituted phenethylaminederivative.[2] It is ananalogue ofepinephrine (3,4,β-trihydroxy-N-methylphenethylamine), ofphenylephrine ((R)-β,3-dihydroxy-N-methylphenethylamine), ofmetaterol (3,β-dihydroxy-N-isopropylphenethylamine), and ofnorfenefrine (3,β-dihydroxyphenethylamine), as well as ofmetaraminol ((1R,2S)-3,β-dihydroxy-α-methylphenethylamine).[2]
Etilefrine pivalate (K-30052) is the 3-pivalylester of etilefrine.[2] In contrast to etilefrine, etilefrine pivalate was never marketed.[2][1]
Etilefrine was first described and introduced for medical use by 1949.[7][8]
Etilefrine is thegeneric name of the drug and itsINNTooltip International Nonproprietary Name andBANTooltip British Approved Name, whileétiléfrine is itsDCFTooltip Dénomination Commune Française andetilefrina is itsDCITTooltip Denominazione Comune Italiana.[2][1] In the case of thehydrochloridesalt, its generic name isetilefrine hydrochloride and this is itsBANMTooltip British Approved Name andJANTooltip Japanese Accepted Name.[2][1] Synonyms of etilefrine includeethylnorphenylephrine,ethylphenephrine,etiladrianol,aethyladrianol, andM-I-36.[2][1][9] Brand names of the drug includeEffortil,Circupon,Apocretin,Palsamin,Kertasin,Pressoton,Effoless, andSanlephrin.[2][1]
