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Details

Stereochemistry RACEMIC
Molecular Formula C10H15NO2
Molecular Weight 181.2316
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ETILEFRINE

SMILES

CCNCC(O)C1=CC=CC(O)=C1

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 181.2316
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment: description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/26240886 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

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Midodrine. A review of its pharmacological properties and therapeutic use in orthostatic hypotension and secondary hypotensive disorders.
1989 Nov
Etilefrine in the prevention of prolonged erection after diagnostic pharmacological stimulation.
1996
Effects of hypertonic 75 mg/ml (7.5%) saline on extracellular water volume when used for preloading before spinal anaesthesia.
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 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
Tilt table test: state of the art.
2003 Oct 1
Randomized clinical trials of neurally mediated syncope.
2003 Sep
[A patient with Shy-Drager syndrome managed under general anesthesia with thoracic epidural anesthesia].
2005 Jul
[Management of postoperative chylothorax].
2006 Apr
Investigational agents for sickle cell disease.
2006 Aug
[Cervical lymphorrea after nodal dissection: role of fasting based on clinical evidence].
2006 Feb
From methylene blue (methylthionine chloride) to Al-Ghorab procedure: the therapy of priapism (our experience).
2009 Dec
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
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:20:22 GMT 2023
Edited
by admin
on Fri Dec 15 16:20:22 GMT 2023
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
S-40032
Code English
S-40032-7
Code English
ETHYLEFRINE
Common Name English
(±)-ETILEFRINE
Common Name English
Etilefrine [WHO-DD]
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 Fri Dec 15 16:20:22 GMT 2023 , Edited by admin on Fri Dec 15 16:20:22 GMT 2023
WHO-VATC QC01CA01
Created by admin on Fri Dec 15 16:20:22 GMT 2023 , Edited by admin on Fri Dec 15 16:20:22 GMT 2023
EU-Orphan Drug EU/3/02/122
Created by admin on Fri Dec 15 16:20:22 GMT 2023 , Edited by admin on Fri Dec 15 16:20:22 GMT 2023
NCI_THESAURUS C29747
Created by admin on Fri Dec 15 16:20:22 GMT 2023 , Edited by admin on Fri Dec 15 16:20:22 GMT 2023
WHO-ATC C01CA01
Created by admin on Fri Dec 15 16:20:22 GMT 2023 , Edited by admin on Fri Dec 15 16:20:22 GMT 2023
WHO-ATC C01CA51
Created by admin on Fri Dec 15 16:20:22 GMT 2023 , Edited by admin on Fri Dec 15 16:20:22 GMT 2023
Code System Code Type Description
DRUG CENTRAL
1101
Created by admin on Fri Dec 15 16:20:22 GMT 2023 , Edited by admin on Fri Dec 15 16:20:22 GMT 2023
PRIMARY
INN
2229
Created by admin on Fri Dec 15 16:20:22 GMT 2023 , Edited by admin on Fri Dec 15 16:20:22 GMT 2023
PRIMARY
ChEMBL
CHEMBL86882
Created by admin on Fri Dec 15 16:20:22 GMT 2023 , Edited by admin on Fri Dec 15 16:20:22 GMT 2023
PRIMARY
NCI_THESAURUS
C65576
Created by admin on Fri Dec 15 16:20:22 GMT 2023 , Edited by admin on Fri Dec 15 16:20:22 GMT 2023
PRIMARY
CAS
10128-36-6
Created by admin on Fri Dec 15 16:20:22 GMT 2023 , Edited by admin on Fri Dec 15 16:20:22 GMT 2023
SUPERSEDED
DRUG BANK
DB08985
Created by admin on Fri Dec 15 16:20:22 GMT 2023 , Edited by admin on Fri Dec 15 16:20:22 GMT 2023
PRIMARY
EVMPD
SUB07303MIG
Created by admin on Fri Dec 15 16:20:22 GMT 2023 , Edited by admin on Fri Dec 15 16:20:22 GMT 2023
PRIMARY
MERCK INDEX
m5184
Created by admin on Fri Dec 15 16:20:22 GMT 2023 , Edited by admin on Fri Dec 15 16:20:22 GMT 2023
PRIMARY Merck Index
CAS
2409-85-0
Created by admin on Fri Dec 15 16:20:22 GMT 2023 , Edited by admin on Fri Dec 15 16:20:22 GMT 2023
SUPERSEDED
RXCUI
4169
Created by admin on Fri Dec 15 16:20:22 GMT 2023 , Edited by admin on Fri Dec 15 16:20:22 GMT 2023
PRIMARY RxNorm
WIKIPEDIA
Etilefrine
Created by admin on Fri Dec 15 16:20:22 GMT 2023 , Edited by admin on Fri Dec 15 16:20:22 GMT 2023
PRIMARY
MESH
D005039
Created by admin on Fri Dec 15 16:20:22 GMT 2023 , Edited by admin on Fri Dec 15 16:20:22 GMT 2023
PRIMARY
FDA UNII
ZB6F8MY53V
Created by admin on Fri Dec 15 16:20:22 GMT 2023 , Edited by admin on Fri Dec 15 16:20:22 GMT 2023
PRIMARY
EPA CompTox
DTXSID1023029
Created by admin on Fri Dec 15 16:20:22 GMT 2023 , Edited by admin on Fri Dec 15 16:20:22 GMT 2023
PRIMARY
SMS_ID
100000082095
Created by admin on Fri Dec 15 16:20:22 GMT 2023 , Edited by admin on Fri Dec 15 16:20:22 GMT 2023
PRIMARY
ECHA (EC/EINECS)
233-359-9
Created by admin on Fri Dec 15 16:20:22 GMT 2023 , Edited by admin on Fri Dec 15 16:20:22 GMT 2023
ALTERNATIVE
ECHA (EC/EINECS)
211-910-4
Created by admin on Fri Dec 15 16:20:22 GMT 2023 , Edited by admin on Fri Dec 15 16:20:22 GMT 2023
PRIMARY
CAS
709-55-7
Created by admin on Fri Dec 15 16:20:22 GMT 2023 , Edited by admin on Fri Dec 15 16:20:22 GMT 2023
PRIMARY
PUBCHEM
3306
Created by admin on Fri Dec 15 16:20:22 GMT 2023 , Edited by admin on Fri Dec 15 16:20:22 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> AGONIST
SALT/SOLVATE -> PARENT
ENANTIOMER -> RACEMATE
TRANSPORTER -> INHIBITOR
ENANTIOMER -> RACEMATE
TRANSPORTER -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY