Etilefrine

Etilefrine
Clinical data
Trade namesEffortil, many others[1][2]
Other namesEtilephrine; Ethylnorphenylephrine; Ethylphenephrine; Ethyladrianol; Etiladrianol; Aethyladrianol; M-I-36; 3,β-Dihydroxy-N-ethylphenethylamine; 3,β-Dihydroxy-N-ethyl-β-phenylethylamine
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral, injection[3][4]
Drug classAdrenergic receptor agonist; Sympathomimetic
ATC code
Pharmacokinetic data
BioavailabilityOral: 50%[3]
Protein binding23% (8.5% to albumin)[3]
MetabolismConjugation (glucuronidation)[3]
Metabolites• Conjugates[3]
• Hydroxymandelic acid (3%)[3]
Elimination half-life2.5 hours[3]
ExcretionUrine (80%; 7–28% unchanged, 44–73% as conjugates)[3]
Identifiers
  • (RS)-3-[2-(ethylamino)-1-hydroxyethyl]phenol
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.010.829 Edit this at Wikidata
Chemical and physical data
FormulaC10H15NO2
Molar mass181.235 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
  • CCNCC(O)c1cc(O)ccc1
  • InChI=1S/C10H15NO2/c1-2-11-7-10(13)8-4-3-5-9(12)6-8/h3-6,10-13H,2,7H2,1H3 checkY
  • Key:SQVIAVUSQAWMKL-UHFFFAOYSA-N checkY
  (verify)

Etilefrine, sold under the brand name Effortil among others, is a sympathomimetic medication used as an antihypotensive agent to treat orthostatic hypotension.[1] It is usually used by mouth, but is also available as an injectable.[3][4]

Side effects of etilefrine include nausea, tremors, and palpitations, among others.[5] Etilefrine is an agonist of the α- and β-adrenergic receptors.[6] It is a substituted phenethylamine and is related to epinephrine, phenylephrine, and norfenefrine.[2]

Etilefrine was first described and introduced for medical use by 1949.[7][8]

  1. ^ a b Cite error: The named reference IndexNominum2004 was invoked but never defined (see the help page).
  2. ^ a b Cite error: The named reference Elks2014 was invoked but never defined (see the help page).
  3. ^ a b c d e f g h i Aviado D, Bowman W, Burnstock G, Greven J, Hannappel J, Juul P, et al. (2012). Adrenergic Activators and Inhibitors: Part II. Handbook of Experimental Pharmacology. Springer Berlin Heidelberg. pp. 364–366. ISBN 978-3-642-67584-3. Retrieved 31 August 2024.
  4. ^ a b Wein A, Kavoussi L, Novick A, Partin A, Peters C (2011). Campbell-Walsh Urology. Elsevier Health Sciences. pp. 758–761. ISBN 978-1-4557-2298-3. Retrieved 2024-08-31.
  5. ^ Cite error: The named reference SkylynnAbelChristopher2024 was invoked but never defined (see the help page).
  6. ^ Graham BA, Wael A, Jack C, Rohan MA, Wayne HJ (August 2022). "An overview of emergency pharmacotherapy for priapism". Expert Opin Pharmacother. 23 (12): 1371–1380. doi:10.1080/14656566.2022.2099271. PMID 35815373.
  7. ^ Cite error: The named reference NeueSpezialitäten1949 was invoked but never defined (see the help page).
  8. ^ Cite error: The named reference Spitzbarth1950 was invoked but never defined (see the help page).