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Details

Stereochemistry RACEMIC
Molecular Formula C10H15NO2
Molecular Weight 181.232
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ETILEFRINE

SMILES

CCNCC(c1cccc(c1)O)O

InChI

InChIKey=SQVIAVUSQAWMKL-UHFFFAOYSA-N
InChI=1S/C10H15NO2/c1-2-11-7-10(13)8-4-3-5-9(12)6-8/h3-6,10-13H,2,7H2,1H3

HIDE SMILES / InChI

Molecular Formula C10H15NO2
Molecular Weight 181.232
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment:: https://en.wikipedia.org/wiki/Etilefrin

Etilefrine is a cardiac stimulant used as an antihypotensive. Intravenous infusion of this compound increases cardiac output, stroke volume, venous return and blood pressure in man and experimental animals, suggesting stimulation of both α and β adrenergic receptors. However, in vitro studies indicate that etilefrine has a much higher affinity for β1 (cardiac) than for β2 adrenoreceptors. Intravenous etilefrine increases the pulse rate, cardiac output, stroke volume, central venous pressure and mean arterial pressure of healthy individuals. Marked falls in pulse rate, cardiac output, stroke volume and peripheral bloodflow, accompanied by rises in mean arterial pressure, occur when etilefrine is infused after administration of intravenous propranolol 2,5 mg. These findings indicate that etilefrine has both β1 and α1 adrenergic effects in man. The French Health Products Agency concluded that etilefrine and heptaminol have an unfavourable harm-benefit balance, and also placed restrictions on the use of midodrine.

Approval Year

Targets

Targets

Conditions

Conditions

PubMed

PubMed

TitleDatePubMed
Etilefrine in the treatment of levodopa-induced orthostatic hypotension.
1973 Aug
Effect of selected drugs on arterial pressure response to upright posture.
1976
Hydroxyethyl starches, dextran and balanced salt solution in correction of hypotension during epidural anaesthesia.
1984 Dec
Midodrine. A review of its pharmacological properties and therapeutic use in orthostatic hypotension and secondary hypotensive disorders.
1989 Nov
Alfentanil combined with vecuronium or pancuronium: haemodynamic implications.
1992 Jul
Etilefrine in the prevention of prolonged erection after diagnostic pharmacological stimulation.
1996
[Ambulatory treatment and prevention of priapism using alpha-agonists. Apropos of 172 cases].
1997 Jan
Effect of midodrine on chlorpromazine-induced orthostatic hypotension in rabbits: comparison with amezinium, etilefrine and droxidopa.
2000 Dec
Acute priapism in a patient with unstable hemoglobin Perth and Factor V Leiden under effective oral anticoagulant therapy.
2001
Effects of hypertonic 75 mg/ml (7.5%) saline on extracellular water volume when used for preloading before spinal anaesthesia.
2001 Jul
Management of sickle cell priapism with etilefrine.
2001 Jul
[Priapism in the course of generalized atopic dermatitis].
2002 Aug-Sep
Hypotension on CAPD: can use of vasoconstrictive drugs be harmful?
2002 Jan-Feb
[Management of priapism in sickle-cell diseases with alpha-adrenergic agonists].
2002 Jul-Sep
Management of thoracic duct injuries after oesophagectomy (Br J Surg 2001: 88: 1442-8). Letter 1.
2002 Jun
Long-term outcome of patients with asystole induced by head-up tilt test.
2002 Mar
Autonomic failure mimicing dopamine agonist induced vertigo in a patient with macroprolactinoma.
2002 Oct
Randomized clinical trials of neurally mediated syncope.
2003 Sep
Priapism in a patient with unstable hemoglobin: hemoglobin Köln.
2003 Sep
The importance of interrupting angiotensin converting enzyme inhibitor treatment before spinal anaesthesia--a controlled case report.
2004
Sequential injection spectrophotometric determination of etilefrine hydrochloride.
2004 Dec
Etilefrine use in the management of post-operative chyle leaks in thoracic surgery.
2004 Mar
[Efficacy and safety of a herbal drug containing hawthorn berries and D-camphor in hypotension and orthostatic circulatory disorders/results of a retrospective epidemiologic cohort study].
2005
Drug specificity and intestinal membrane localization of human organic cation transporters (OCT).
2005 Dec 5
Apical uptake of choline and cationic drugs in epithelial cell lines derived from human placenta.
2005 Feb-Mar
[A patient with Shy-Drager syndrome managed under general anesthesia with thoracic epidural anesthesia].
2005 Jul
Intracavernosal etilefrine self-injection therapy for recurrent priapism: one decade of follow-up.
2005 May
Indications, surgical technique, and long-term experience with laparoscopic closure of the nephrosplenic space in standing horses.
2005 Nov-Dec
Effects of cafedrine/theodrenaline, etilefrine and ephedrine on uterine blood flow during epidural-induced hypotension in pregnant sheep.
2005 Sep-Oct
[Management of postoperative chylothorax].
2006 Apr
Chylothorax.
2006 Aug
[Cervical lymphorrea after nodal dissection: role of fasting based on clinical evidence].
2006 Feb
[Ephedrine and etilefrine as vasopressor to correct maternal arterial hypotension during elective cesarean section under spinal anesthesia. Comparative study].
2006 Jun
Clinical observations surrounding an increased incidence of postanesthetic myopathy in halothane-anesthetized horses.
2006 Mar
Anaesthesia with remifentanil infusion in diabetic versus non-diabetic patients undergoing vitrectomy. A Holter-controlled study.
2007
[Post-surgical lymphocutaneous fistula, chylous ascites and chylothorax--infrequent but serious complications: etiology, diagnosis and therapeutic options].
2007 Dec
Dissociation between cortical activation and cognitive performance under pharmacological blood pressure elevation in chronic hypotension.
2007 Jul
[A complicated course after esophagogastrectomy].
2007 May-Jun
Development and validation of a liquid chromatography-tandem mass spectrometry method for the determination of phenylephrine in human plasma and its application to a pharmacokinetic study.
2007 Oct 15
Stuttering priapism--a review of the therapeutic options.
2008 Aug
Chylous ascites following radical nephrectomy: a case report.
2008 Jan 11
Effect of systemic blood pressure on microcollateral circulation evaluated by real-time contrast echocardiography.
2008 Jun
From methylene blue (methylthionine chloride) to Al-Ghorab procedure: the therapy of priapism (our experience).
2009 Dec
alpha-Adrenoceptor agonists for the treatment of vasovagal syncope: a meta-analysis of worldwide published data.
2009 Jul
Etilefrinhydrochloride tablet ingestion: successful therapy by endoscopic removal of tablet conglomerate.
2009 Mar-Apr
Epidemiological analysis of doping offences in the professional tennis circuit.
2010 Dec 15
[Emergency checklist: priapism].
2010 Feb 11
Bilateral anterior ischemic optic neuropathy in patients on dialysis: A report of two cases.
2010 Jan
Comparison of two protective lung ventilatory regimes on oxygenation during one-lung ventilation: a randomized controlled trial.
2010 Nov 2
Patents

Patents

Sample Use Guides

15 mg (30 drops)
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Sat Jun 26 03:09:59 UTC 2021
Edited
by admin
on Sat Jun 26 03:09:59 UTC 2021
Record UNII
ZB6F8MY53V
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ETILEFRINE
INN   WHO-DD  
INN  
Official Name English
BENZENEMETHANOL, .ALPHA.-((ETHYLAMINO)METHYL)-3-HYDROXY-
Systematic Name English
CORCANFOL
Brand Name English
ETILEFRINE [INN]
Common Name English
.ALPHA.-(M-HYDROXYPHENYL)-.BETA.-(ETHYLAMINO)ETHANOL
Systematic Name English
DL-ETILEFRIN
Common Name English
ETILEFRINE [WHO-DD]
Common Name English
S-40032
Code English
S-40032-7
Code English
ETHYLEFRINE
Common Name English
(+/-)-ETILEFRINE
Common Name English
N-ETHYLNORPHENYLEPHRINE
Common Name English
1-(3-HYDROXYPHENYL)-2-(ETHYLAMINO)ETHANOL
Systematic Name English
ETILEFRIN
Common Name English
.ALPHA.-((ETHYLAMINO)METHYL)-M-HYDROXYBENZYL ALCOHOL
Systematic Name English
ETILEFRIN [MI]
Common Name English
BENZYL ALCOHOL, .ALPHA.-((ETHYLAMINO)METHYL)-M-HYDROXY-
Systematic Name English
Classification Tree Code System Code
WHO-VATC QC01CA51
Created by admin on Sat Jun 26 03:09:59 UTC 2021 , Edited by admin on Sat Jun 26 03:09:59 UTC 2021
WHO-VATC QC01CA01
Created by admin on Sat Jun 26 03:09:59 UTC 2021 , Edited by admin on Sat Jun 26 03:09:59 UTC 2021
EU-Orphan Drug EU/3/02/122
Created by admin on Sat Jun 26 03:09:59 UTC 2021 , Edited by admin on Sat Jun 26 03:09:59 UTC 2021
NCI_THESAURUS C29747
Created by admin on Sat Jun 26 03:09:59 UTC 2021 , Edited by admin on Sat Jun 26 03:09:59 UTC 2021
WHO-ATC C01CA01
Created by admin on Sat Jun 26 03:09:59 UTC 2021 , Edited by admin on Sat Jun 26 03:09:59 UTC 2021
WHO-ATC C01CA51
Created by admin on Sat Jun 26 03:09:59 UTC 2021 , Edited by admin on Sat Jun 26 03:09:59 UTC 2021
Code System Code Type Description
DRUG CENTRAL
1101
Created by admin on Sat Jun 26 03:09:59 UTC 2021 , Edited by admin on Sat Jun 26 03:09:59 UTC 2021
PRIMARY
INN
2229
Created by admin on Sat Jun 26 03:09:59 UTC 2021 , Edited by admin on Sat Jun 26 03:09:59 UTC 2021
PRIMARY
ChEMBL
CHEMBL86882
Created by admin on Sat Jun 26 03:09:59 UTC 2021 , Edited by admin on Sat Jun 26 03:09:59 UTC 2021
PRIMARY
NCI_THESAURUS
C65576
Created by admin on Sat Jun 26 03:09:59 UTC 2021 , Edited by admin on Sat Jun 26 03:09:59 UTC 2021
PRIMARY
CAS
10128-36-6
Created by admin on Sat Jun 26 03:09:59 UTC 2021 , Edited by admin on Sat Jun 26 03:09:59 UTC 2021
SUPERSEDED
DRUG BANK
DB08985
Created by admin on Sat Jun 26 03:09:59 UTC 2021 , Edited by admin on Sat Jun 26 03:09:59 UTC 2021
PRIMARY
EVMPD
SUB07303MIG
Created by admin on Sat Jun 26 03:09:59 UTC 2021 , Edited by admin on Sat Jun 26 03:09:59 UTC 2021
PRIMARY
MERCK INDEX
M5184
Created by admin on Sat Jun 26 03:09:59 UTC 2021 , Edited by admin on Sat Jun 26 03:09:59 UTC 2021
PRIMARY Merck Index
CAS
2409-85-0
Created by admin on Sat Jun 26 03:09:59 UTC 2021 , Edited by admin on Sat Jun 26 03:09:59 UTC 2021
SUPERSEDED
RXCUI
4169
Created by admin on Sat Jun 26 03:09:59 UTC 2021 , Edited by admin on Sat Jun 26 03:09:59 UTC 2021
PRIMARY RxNorm
WIKIPEDIA
Etilefrine
Created by admin on Sat Jun 26 03:09:59 UTC 2021 , Edited by admin on Sat Jun 26 03:09:59 UTC 2021
PRIMARY
MESH
D005039
Created by admin on Sat Jun 26 03:09:59 UTC 2021 , Edited by admin on Sat Jun 26 03:09:59 UTC 2021
PRIMARY
FDA UNII
ZB6F8MY53V
Created by admin on Sat Jun 26 03:09:59 UTC 2021 , Edited by admin on Sat Jun 26 03:09:59 UTC 2021
PRIMARY
EPA CompTox
709-55-7
Created by admin on Sat Jun 26 03:09:59 UTC 2021 , Edited by admin on Sat Jun 26 03:09:59 UTC 2021
PRIMARY
ECHA (EC/EINECS)
233-359-9
Created by admin on Sat Jun 26 03:09:59 UTC 2021 , Edited by admin on Sat Jun 26 03:09:59 UTC 2021
ALTERNATIVE
ECHA (EC/EINECS)
211-910-4
Created by admin on Sat Jun 26 03:09:59 UTC 2021 , Edited by admin on Sat Jun 26 03:09:59 UTC 2021
PRIMARY
CAS
709-55-7
Created by admin on Sat Jun 26 03:09:59 UTC 2021 , Edited by admin on Sat Jun 26 03:09:59 UTC 2021
PRIMARY
PUBCHEM
3306
Created by admin on Sat Jun 26 03:09:59 UTC 2021 , Edited by admin on Sat Jun 26 03:09:59 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
ENANTIOMER -> RACEMATE
TARGET -> AGONIST
ENANTIOMER -> RACEMATE
TRANSPORTER -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY