Chemical compound
Pharmaceutical compound
Etilefrine , sold under the brand nameEffortil among others, is asympathomimetic medication used as anantihypotensive agent to treatorthostatic hypotension .[ 1] by mouth , but is also available as aninjectable .[ 3] [ 4]
Side effects of etilefrine includenausea ,tremors , andpalpitations , among others.[ 5] agonist of theα- andβ-adrenergic receptors .[ 6] substituted 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] off-label to treatpriapism .[ 6] [ 9]
Side effects of etilefrine includenausea ,tremors , andpalpitations , among others.[ 5]
Etilefrine is anagonist of theα1 -adrenergic receptor .[ 5] vasoconstrictor andantihypotensive agent .[ 5] β1 -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] in vitro 1 (cardiac) than for β2 adrenoreceptors .[ 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] bioavailability of etilefrine is approximately 50%.[ 3] Peak concentrations of etilefrine occur after 30 minutes.[ 3]
Theplasma protein binding of etilefrine is 23%.[ 3] albumin .[ 3]
Etilefrine is aperipherally selective drug .[ 16]
Etilefrine ismetabolized byconjugation , for instanceglucuronidation , in theliver andgastrointestinal tract .[ 3] first-pass metabolism .[ 3] [ 3]
Theelimination of etilefrine is dependent onroute of administration .[ 3] excreted inurine within 24 hours.[ 3] [ 3] [ 3]
Etilefrine, also known as 3,β-dihydroxy-N -ethylphenethylamine, is asubstituted phenethylamine derivative .[ 2] analogue 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-pivalyl ester of etilefrine.[ 2] [ 2] [ 1]
Etilefrine was first described and introduced for medical use by 1949.[ 7] [ 8]
Society and culture [ edit ] Etilefrine is thegeneric name of the drug and itsINN Tooltip International Nonproprietary Name andBAN Tooltip British Approved Name , whileétiléfrine is itsDCF Tooltip Dénomination Commune Française andetilefrina is itsDCIT Tooltip Denominazione Comune Italiana .[ 2] [ 1] hydrochloride salt , its generic name isetilefrine hydrochloride and this is itsBANM Tooltip British Approved Name andJAN Tooltip Japanese Accepted Name .[ 2] [ 1] ethylnorphenylephrine ,ethylphenephrine ,etiladrianol ,aethyladrianol , andM-I-36 .[ 2] [ 1] [ 9] Effortil ,Circupon ,Apocretin ,Palsamin ,Kertasin ,Pressoton ,Effoless , andSanlephrin .[ 2] [ 1]
^a b c d e f g Schweizerischer Apotheker-Verein (2004).Index Nominum: International Drug Directory ISBN 978-3-88763-101-7 . Retrieved2024-08-31 . ^a b c d e f g h i j Elks J (2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies ISBN 978-1-4757-2085-3 . Retrieved2024-08-31 . ^a b c d e f g h i j k l m n o p q r s t u Aviado D, Bowman W, Burnstock G, Greven J, Hannappel J, Juul P, et al. (2012).Adrenergic Activators and Inhibitors: Part II 364– 366.ISBN 978-3-642-67584-3 . Retrieved31 August 2024 . ^a b Wein A, Kavoussi L, Novick A, Partin A, Peters C (2011).Campbell-Walsh Urology 758– 761.ISBN 978-1-4557-2298-3 . Retrieved2024-08-31 . ^a b c d e Skylynn T, Abel T, Christopher L, Suliman G, Dominic R, Joel V, et al. (January 2024)."Benefits and Risks of Medications Used in the Management of Hypotension: A Review" .Cureus .16 (1) e51608.doi :10.7759/cureus.51608 PMC 10837047 PMID 38313995 . ^a b 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 . ^a b "Neue Spezialitäten".Klinische Wochenschrift (in German).28 (19– 20): 350. 1950.doi :10.1007/BF01485958 .ISSN 0023-2173 . ^a b Spitzbarth H (December 1950). "[Results with effortil in arterial hypotension]".Medizinische Klinik (in German).45 (50):1593– 1596.PMID 14815173 . ^a b c d Docherty JR (June 2008)."Pharmacology of stimulants prohibited by the World Anti-Doping Agency (WADA)" .Br J Pharmacol .154 (3):606– 622.doi :10.1038/bjp.2008.124 .PMC 2439527 PMID 18500382 . ^ Nusser E, Donath H, Russ W (August 1965). "[On the circulatory action of depot-Effortil in patients with hypotonic regulation circulator disorders]".Die Medizinische Welt (in German).32 :1824– 7.PMID 5320529 . ^ Mellander S (1966). "Comparative effects of acetylcholine, butyl-nor-synephrine (Vasculat), noradrenaline, and ethyl-adrainol (Effonti) on resistance, capacitance, and precapillary sphincter vessels and capillary filtration in cat skeletal muscle".Angiologica .3 (2):77– 99.doi :10.1159/000157650 .PMID 4380206 . ^ von Limbourg P, Just H, Lang KF (1973). "Positive inotrope Wirkung von Etilefrinhydrochlorid (EffortilR)".Kardiol .586 : 1. ^ Tarnow J, Brückner JB, Eberlein HG, Patschke D, Reinecke A, Schmicke P (1973). "Experimentelle Untersuchungen zur Beeinflussung der Hämodynamik in tiefer Halothannarkose durch Dopamin, Glucagon, Effortil, Noradrenalin und Dextran".Der Anaesthesist .22 :8– 15. ^ Carrera AL, Aguilera AM (1973). "Algunos effectos circulatorios de la m− oxifenil etanol etilmaina y sus modificaciones por el bloqueo α y β adrenergico".Arch. Inst. Cardiol .43 . Mexico:279– 287. ^ Offermeier J, Dreyer AC (March 1971)."A comparison of the effects of noradrenaline, adrenaline and some phenylephrine derivatives on alpha-, beta1 - and beta2 - adrenergic receptors" (PDF) .South African Medical Journal = Suid-Afrikaanse Tydskrif vir Geneeskunde .45 (10):265– 267.PMID 4396765 . ^ Calkins H (October 1999)."Pharmacologic approaches to therapy for vasovagal syncope" .Am J Cardiol .84 (8A):20Q – 25Q .doi :10.1016/s0002-9149(99)00626-8 PMID 10568557 .
α1
Agonists Antagonists Abanoquil ADRIANA Ajmalicine Alfuzosin Anisodamine Anisodine Atiprosin Atypical antipsychotics (e.g.,brexpiprazole ,clozapine ,olanzapine ,quetiapine ,risperidone )Benoxathian Beta blockers (e.g.,adimolol ,amosulalol ,arotinolol ,carvedilol ,eugenodilol ,labetalol )Buflomedil Bunazosin Corynanthine Dapiprazole Domesticine Doxazosin Ergolines (e.g.,acetergamine ,ergotamine ,dihydroergotamine ,lisuride ,nicergoline ,terguride )Etoperidone Fenspiride Hydroxyzine Indoramin Ketanserin L-765,314 mCPP Mepiprazole Metazosin Monatepil Moxisylyte Naftopidil Nantenine Neldazosin Niaprazine Niguldipine Pardoprunox Pelanserin Perlapine Phendioxan Phenoxybenzamine Phentolamine Phenylpiperazine antidepressants (e.g.,hydroxynefazodone ,nefazodone ,trazodone ,triazoledione )Piperoxan Prazosin Quinazosin Quinidine Silodosin Spegatrine Spiperone Talipexole Tamsulosin Terazosin Tiodazosin Tolazoline Tetracyclic antidepressants (e.g.,amoxapine ,maprotiline ,mianserin )Tricyclic antidepressants (e.g.,amitriptyline ,clomipramine ,doxepin ,imipramine ,trimipramine )Trimazosin Typical antipsychotics (e.g.,chlorpromazine ,fluphenazine ,loxapine ,thioridazine )Urapidil WB-4101 Zolertine
α2
Agonists Antagonists 1-PP Adimolol Amesergide Aptazapine Atipamezole Atypical antipsychotics (e.g.,asenapine ,brexpiprazole ,clozapine ,lurasidone ,olanzapine ,paliperidone ,quetiapine ,risperidone ,zotepine )Azapirones (e.g.,buspirone ,gepirone ,ipsapirone ,tandospirone )BRL-44408 Buflomedil Cirazoline Efaroxan Esmirtazapine Fenmetozole Fluparoxan Idazoxan Ketanserin Lisuride mCPP Mianserin Mirtazapine NAN-190 Pardoprunox Phentolamine Phenoxybenzamine Piperoxan Piribedil Rauwolscine Rotigotine Setiptiline Spegatrine Spiroxatrine Sunepitron Terguride Tolazoline Typical antipsychotics (e.g.,chlorpromazine ,fluphenazine ,loxapine ,thioridazine )Yohimbine
β
Phenethylamines Amphetamines Phentermines Cathinones Phenylisobutylamines (and further-extended) Catecholamines (and close relatives) Cyclized
Phenylalkylpyrrolidines 2-Benzylpiperidines (phenidates ) Phenylmorpholines (phenmetrazines) Phenyloxazolamines (aminorexes) Isoquinolines andtetrahydroisoquinolines 2-Aminoindanes 2-Aminotetralins Others / unsorted 1-Aminomethylindanes (e.g.,2CB-Ind ,AMMI ,bromojimscaline ,jimscaline )2-ADN 2-Benzhydrylpyrrolidine 2C-B-5-hemiFLY-α6 (BNAP) 2C-B-PYR 2CBecca 2CB7 2CJP 2CLisaB 2CLisaH 3-Benzazepines (e.g.,fenoldopam ,lorcaserin ,7-chlorolorcaserin ,SCHEMBL5334361 )3-Benzhydrylmorpholine 3-Phenylpiperidines (e.g.,3-phenylpiperidine ,3-PPP ,OSU-6162 (PNU-96391) ,LPH-5 ,LPH-48 ,Z3517967757 (Z7757) )6-AB AL-1095 Aminochromes (e.g.,adrenochrome ,adrenolutin )Benzocyclobutenes (e.g.,2CBCB-NBOMe ,bromotomscaline ,S33005 ,TCB-2 ,tomscaline )Benzoxepins (e.g.,BBOX ,IBOX ,TFMBOX )Butyltolylquinuclidine Camfetamine Cypenamine (trans -2-phenylcyclopentylamine) Diphenidine Diphenylprolinol DMBMPP Ergolines (e.g.,LSD )Fencamfamin GYKI-52895 HDMP-29 Ivabradine Methoxphenidine Methylmorphenate Milnacipran MT-45 2-Naphthylamine Org 6582 Partial ergolines (e.g.,NDTDI ,RU-27849 ,DEIMDHPCA ,DEMPDHPCA ,DEMPDHPCA-2C-D ,RU-27251 )PF-592,379 Phenylcyclopropylamines (e.g.,DMCPA ,TMT ,tranylcypromine )Phenylpiracetams (e.g.,phenylpiracetam ,MRZ-9547 ,RGPU-95 )Pyridopyrroloquinoxalines (e.g.,lumateperone ,deulumateperone ,IHCH-7079 ,IHCH-7086 ,IHCH-7113 ,ITI-1549 )Tetrahydrobenzopyranylamines (e.g.,CT-5126 )Tolazoline Tricyclics (e.g.,AMDA ,AMDH ,benzoctamine ,dizocilpine ,SpAMDA )ZC-B
Related compounds 2-Furylethylamine 2-Pyrrolylethylamine 3-Pyrrolylethylamine 3-Pyrrolylpropylamine 2-Tetrahydrofurylethylamine 4-Benzylpiperidine 7-AB Alkylamines (e.g.,1,3-DMBA Tooltip 1,3-dimethylbutylamine ,1,4-DMAA Tooltip 1,4-dimethylamylamine ,heptaminol ,iproheptine ,isometheptene ,methylhexanamine/ 1,3-DMAA ,octodrine ,oenethyl ,tuaminoheptane )Benzylamines (e.g.,benzylamine ,α-methylbenzylamine ,MDM1EA ,ALPHA ,M-ALPHA ,pargyline )Benzylpiperazines (e.g.,benzylpiperazine ,MDBZP ,fipexide )Cyclohexylaminopropanes (e.g.,propylhexedrine ,norpropylhexedrine )Cyclopentylaminopropanes (e.g.,isocyclamine ,cyclopentamine )Phenoxyethylamines (e.g.,3,4,5-trimethoxyphenoxyethylamine ,CT-4719 ,ORG-37684 )Phenylalkenylamines (e.g.,phenylbutenamine )Phenylalkynylamines (e.g.,phenylbutynamine )Phenylpiperazines (e.g.,1-phenylpiperazine ,mCPP Tooltip meta-chlorophenylpiperazine ,TFMPP Tooltip trifluoromethylphenylpiperazine ,oMPP Tooltip ortho-methylphenylpiperazine ,pFPP Tooltip para-fluorophenylpiperazine ,pMeOPP Tooltip para-methoxyphenylpiperazine )Phenylpropylamines (e.g.,phenylpropylamine ,homo-MDA ,homo-MDMA )Thienylaminopropanes (thiopropamines) (e.g.,thiopropamine ,methiopropamine ,thiothinone )
