U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C15H23NO3
Molecular Weight 265.348
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ETILEFRINE PIVALATE

SMILES

CCNCC(O)C1=CC(OC(=O)C(C)(C)C)=CC=C1

InChI

InChIKey=DRMHNJGOEAYOIZ-UHFFFAOYSA-N
InChI=1S/C15H23NO3/c1-5-16-10-13(17)11-7-6-8-12(9-11)19-14(18)15(2,3)4/h6-9,13,16-17H,5,10H2,1-4H3

HIDE SMILES / InChI

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
Epidemiological analysis of doping offences in the professional tennis circuit.
2010-12-15
Comparison of two protective lung ventilatory regimes on oxygenation during one-lung ventilation: a randomized controlled trial.
2010-11-02
[Emergency checklist: priapism].
2010-02-11
Bilateral anterior ischemic optic neuropathy in patients on dialysis: A report of two cases.
2010-01
From methylene blue (methylthionine chloride) to Al-Ghorab procedure: the therapy of priapism (our experience).
2009-12
alpha-Adrenoceptor agonists for the treatment of vasovagal syncope: a meta-analysis of worldwide published data.
2009-07
Etilefrinhydrochloride tablet ingestion: successful therapy by endoscopic removal of tablet conglomerate.
2009-02-10
Stuttering priapism--a review of the therapeutic options.
2008-08
Effect of systemic blood pressure on microcollateral circulation evaluated by real-time contrast echocardiography.
2008-06
Chylous ascites following radical nephrectomy: a case report.
2008-01-11
[Post-surgical lymphocutaneous fistula, chylous ascites and chylothorax--infrequent but serious complications: etiology, diagnosis and therapeutic options].
2007-12
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.
2007-10-15
[A complicated course after esophagogastrectomy].
2007-10-11
Dissociation between cortical activation and cognitive performance under pharmacological blood pressure elevation in chronic hypotension.
2007-07
Anaesthesia with remifentanil infusion in diabetic versus non-diabetic patients undergoing vitrectomy. A Holter-controlled study.
2007
Chylothorax.
2006-08
Investigational agents for sickle cell disease.
2006-08
[Ephedrine and etilefrine as vasopressor to correct maternal arterial hypotension during elective cesarean section under spinal anesthesia. Comparative study].
2006-06
[Management of postoperative chylothorax].
2006-04
Clinical observations surrounding an increased incidence of postanesthetic myopathy in halothane-anesthetized horses.
2006-03
[Cervical lymphorrea after nodal dissection: role of fasting based on clinical evidence].
2006-02
Indications, surgical technique, and long-term experience with laparoscopic closure of the nephrosplenic space in standing horses.
2005-12-14
Drug specificity and intestinal membrane localization of human organic cation transporters (OCT).
2005-12-05
[A patient with Shy-Drager syndrome managed under general anesthesia with thoracic epidural anesthesia].
2005-07
Intracavernosal etilefrine self-injection therapy for recurrent priapism: one decade of follow-up.
2005-05
[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
Sequential injection spectrophotometric determination of etilefrine hydrochloride.
2004-12
Apical uptake of choline and cationic drugs in epithelial cell lines derived from human placenta.
2004-05-03
Etilefrine use in the management of post-operative chyle leaks in thoracic surgery.
2004-03
The importance of interrupting angiotensin converting enzyme inhibitor treatment before spinal anaesthesia--a controlled case report.
2004
Effects of cafedrine/theodrenaline, etilefrine and ephedrine on uterine blood flow during epidural-induced hypotension in pregnant sheep.
2003-11-27
Tilt table test: state of the art.
2003-10-01
Randomized clinical trials of neurally mediated syncope.
2003-09
Priapism in a patient with unstable hemoglobin: hemoglobin Köln.
2003-09
[Management of priapism in sickle-cell diseases with alpha-adrenergic agonists].
2002-12-11
[Priapism in the course of generalized atopic dermatitis].
2002-11-21
Autonomic failure mimicing dopamine agonist induced vertigo in a patient with macroprolactinoma.
2002-10
Etilefrine for the prevention of priapism in adult sickle cell disease.
2002-09
Management of thoracic duct injuries after oesophagectomy (Br J Surg 2001: 88: 1442-8). Letter 1.
2002-06
Hypotension on CAPD: can use of vasoconstrictive drugs be harmful?
2002-04-04
Long-term outcome of patients with asystole induced by head-up tilt test.
2002-03
Effects of hypertonic 75 mg/ml (7.5%) saline on extracellular water volume when used for preloading before spinal anaesthesia.
2001-07
Acute priapism in a patient with unstable hemoglobin Perth and Factor V Leiden under effective oral anticoagulant therapy.
2001
[Ambulatory treatment and prevention of priapism using alpha-agonists. Apropos of 172 cases].
1997-01
Etilefrine in the prevention of prolonged erection after diagnostic pharmacological stimulation.
1996
Alfentanil combined with vecuronium or pancuronium: haemodynamic implications.
1992-07
Midodrine. A review of its pharmacological properties and therapeutic use in orthostatic hypotension and secondary hypotensive disorders.
1989-11
Hydroxyethyl starches, dextran and balanced salt solution in correction of hypotension during epidural anaesthesia.
1984-12
Effect of selected drugs on arterial pressure response to upright posture.
1976
Etilefrine in the treatment of levodopa-induced orthostatic hypotension.
1973-08
Patents

Patents

Sample Use Guides

15 mg (30 drops)
Route of Administration: Oral
In Vitro Use Guide
Unknown
Name Type Language
PROPANOIC ACID, 2,2-DIMETHYL-, 3-(2-(ETHYLAMINO)-1-HYDROXYETHYL)PHENYL ESTER
Preferred Name English
ETILEFRINE PIVALATE
INN  
INN  
Official Name English
etilefrine pivalate [INN]
Common Name English
(±)-M-((ETHYLAMINO)-1-HYDROXYETHYL)PHENYL PIVALATE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C29747
Created by admin on Wed Apr 02 07:07:34 GMT 2025 , Edited by admin on Wed Apr 02 07:07:34 GMT 2025
Code System Code Type Description
SMS_ID
100000082076
Created by admin on Wed Apr 02 07:07:34 GMT 2025 , Edited by admin on Wed Apr 02 07:07:34 GMT 2025
PRIMARY
INN
5448
Created by admin on Wed Apr 02 07:07:34 GMT 2025 , Edited by admin on Wed Apr 02 07:07:34 GMT 2025
PRIMARY
PUBCHEM
157211
Created by admin on Wed Apr 02 07:07:34 GMT 2025 , Edited by admin on Wed Apr 02 07:07:34 GMT 2025
PRIMARY
FDA UNII
3RLD929C4S
Created by admin on Wed Apr 02 07:07:34 GMT 2025 , Edited by admin on Wed Apr 02 07:07:34 GMT 2025
PRIMARY
DRUG CENTRAL
4824
Created by admin on Wed Apr 02 07:07:34 GMT 2025 , Edited by admin on Wed Apr 02 07:07:34 GMT 2025
PRIMARY
CAS
85750-39-6
Created by admin on Wed Apr 02 07:07:34 GMT 2025 , Edited by admin on Wed Apr 02 07:07:34 GMT 2025
PRIMARY
NCI_THESAURUS
C65577
Created by admin on Wed Apr 02 07:07:34 GMT 2025 , Edited by admin on Wed Apr 02 07:07:34 GMT 2025
PRIMARY
MESH
C046842
Created by admin on Wed Apr 02 07:07:34 GMT 2025 , Edited by admin on Wed Apr 02 07:07:34 GMT 2025
PRIMARY
EVMPD
SUB07304MIG
Created by admin on Wed Apr 02 07:07:34 GMT 2025 , Edited by admin on Wed Apr 02 07:07:34 GMT 2025
PRIMARY
ChEMBL
CHEMBL2105571
Created by admin on Wed Apr 02 07:07:34 GMT 2025 , Edited by admin on Wed Apr 02 07:07:34 GMT 2025
PRIMARY