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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

Molecular Formula C15H23NO3
Molecular Weight 265.348
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
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
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
Acute priapism in a patient with unstable hemoglobin Perth and Factor V Leiden under effective oral anticoagulant therapy.
2001
Management of sickle cell priapism with etilefrine.
2001 Jul
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
Autonomic failure mimicing dopamine agonist induced vertigo in a patient with macroprolactinoma.
2002 Oct
Etilefrine for the prevention of priapism in adult sickle cell disease.
2002 Sep
Tilt table test: state of the art.
2003 Oct 1
Randomized clinical trials of neurally mediated syncope.
2003 Sep
Priapism in a patient with unstable hemoglobin: hemoglobin Köln.
2003 Sep
Etilefrine use in the management of post-operative chyle leaks in thoracic surgery.
2004 Mar
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
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
Investigational agents for sickle cell disease.
2006 Aug
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
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 Sat Dec 16 16:05:24 GMT 2023
Edited
by admin
on Sat Dec 16 16:05:24 GMT 2023
Record UNII
3RLD929C4S
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ETILEFRINE PIVALATE
INN  
INN  
Official Name English
etilefrine pivalate [INN]
Common Name English
(±)-M-((ETHYLAMINO)-1-HYDROXYETHYL)PHENYL PIVALATE
Systematic Name English
PROPANOIC ACID, 2,2-DIMETHYL-, 3-(2-(ETHYLAMINO)-1-HYDROXYETHYL)PHENYL ESTER
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C29747
Created by admin on Sat Dec 16 16:05:24 GMT 2023 , Edited by admin on Sat Dec 16 16:05:24 GMT 2023
Code System Code Type Description
SMS_ID
100000082076
Created by admin on Sat Dec 16 16:05:24 GMT 2023 , Edited by admin on Sat Dec 16 16:05:24 GMT 2023
PRIMARY
INN
5448
Created by admin on Sat Dec 16 16:05:24 GMT 2023 , Edited by admin on Sat Dec 16 16:05:24 GMT 2023
PRIMARY
PUBCHEM
157211
Created by admin on Sat Dec 16 16:05:24 GMT 2023 , Edited by admin on Sat Dec 16 16:05:24 GMT 2023
PRIMARY
FDA UNII
3RLD929C4S
Created by admin on Sat Dec 16 16:05:24 GMT 2023 , Edited by admin on Sat Dec 16 16:05:24 GMT 2023
PRIMARY
DRUG CENTRAL
4824
Created by admin on Sat Dec 16 16:05:24 GMT 2023 , Edited by admin on Sat Dec 16 16:05:24 GMT 2023
PRIMARY
CAS
85750-39-6
Created by admin on Sat Dec 16 16:05:24 GMT 2023 , Edited by admin on Sat Dec 16 16:05:24 GMT 2023
PRIMARY
NCI_THESAURUS
C65577
Created by admin on Sat Dec 16 16:05:24 GMT 2023 , Edited by admin on Sat Dec 16 16:05:24 GMT 2023
PRIMARY
MESH
C046842
Created by admin on Sat Dec 16 16:05:24 GMT 2023 , Edited by admin on Sat Dec 16 16:05:24 GMT 2023
PRIMARY
EVMPD
SUB07304MIG
Created by admin on Sat Dec 16 16:05:24 GMT 2023 , Edited by admin on Sat Dec 16 16:05:24 GMT 2023
PRIMARY
ChEMBL
CHEMBL2105571
Created by admin on Sat Dec 16 16:05:24 GMT 2023 , Edited by admin on Sat Dec 16 16:05:24 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY