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Details

Stereochemistry RACEMIC
Molecular Formula C10H15NO2.ClH
Molecular Weight 217.693
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ETILEFRINE HYDROCHLORIDE

SMILES

Cl.CCNCC(O)C1=CC=CC(O)=C1

InChI

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

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 ( + / - )

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
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
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
[Management of priapism in sickle-cell diseases with alpha-adrenergic agonists].
2002 Jul-Sep
Etilefrine for the prevention of priapism in adult sickle cell disease.
2002 Sep
[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
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
[Ephedrine and etilefrine as vasopressor to correct maternal arterial hypotension during elective cesarean section under spinal anesthesia. Comparative study].
2006 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
Bilateral anterior ischemic optic neuropathy in patients on dialysis: A report of two cases.
2010 Jan
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 15:02:43 GMT 2023
Edited
by admin
on Fri Dec 15 15:02:43 GMT 2023
Record UNII
ZBI6Q5FH3S
Record Status Validated (UNII)
Record Version
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Name Type Language
ETILEFRINE HYDROCHLORIDE
EP   MART.   WHO-DD  
Common Name English
CARDANAT
Brand Name English
PHETANOL
Brand Name English
ETILEFRINE HYDROCHLORIDE [JAN]
Common Name English
ETILEFRIN HYDROCHLORIDE [MI]
Common Name English
EFFONTIL
Brand Name English
(±)-ETHYLPHENYLEPHRINE HYDROCHLORIDE
Common Name English
DL-1-(3-HYDROXYPHENYL)-1-HYDROXY-2-ETHYLAMINOETHANE HYDROCHLORIDE
Common Name English
APOCRETIN
Brand Name English
ETHLYPHENYLEPHRINE HYDROCHLORIDE, DL
Common Name English
Etilefrine hydrochloride [WHO-DD]
Common Name English
THOMASIN
Brand Name English
CIRCUPON
Brand Name English
ETILEFRINE HYDROCHLORIDE [MART.]
Common Name English
PULSAMIN
Brand Name English
BENZENEMETHANOL, .ALPHA.-((ETHYLAMINO)METHYL)-3-HYDROXY-, HYDROCHLORIDE (1:1)
Systematic Name English
KERTASIN
Brand Name English
ETHYLPHENYLEPHRINE HYDROCHLORIDE, DL-
Common Name English
ETILEFRINE HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
EFFORTIL
Brand Name English
(±)-N-ETHYLNORPHENYLEPHRINE HYDROCHLORIDE
Common Name English
UPDORMIN
Brand Name English
EFORTIL
Brand Name English
ETILEFRINE HCL
Common Name English
(RS)-2-ETHYLAMINO-1-(3-HYDROXYPHENYL)ETHANOL MONOHYDROCHLORIDE
Systematic Name English
BENZYL ALCOHOL, .ALPHA.-((ETHYLAMINO)METHYL)-M-HYDROXY-, HYDROCHLORIDE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C29747
Created by admin on Fri Dec 15 15:02:43 GMT 2023 , Edited by admin on Fri Dec 15 15:02:43 GMT 2023
Code System Code Type Description
EVMPD
SUB02041MIG
Created by admin on Fri Dec 15 15:02:43 GMT 2023 , Edited by admin on Fri Dec 15 15:02:43 GMT 2023
PRIMARY
EPA CompTox
DTXSID1045322
Created by admin on Fri Dec 15 15:02:43 GMT 2023 , Edited by admin on Fri Dec 15 15:02:43 GMT 2023
PRIMARY
PUBCHEM
13668
Created by admin on Fri Dec 15 15:02:43 GMT 2023 , Edited by admin on Fri Dec 15 15:02:43 GMT 2023
PRIMARY
NCI_THESAURUS
C75931
Created by admin on Fri Dec 15 15:02:43 GMT 2023 , Edited by admin on Fri Dec 15 15:02:43 GMT 2023
PRIMARY
SMS_ID
100000087496
Created by admin on Fri Dec 15 15:02:43 GMT 2023 , Edited by admin on Fri Dec 15 15:02:43 GMT 2023
PRIMARY
ChEMBL
CHEMBL86882
Created by admin on Fri Dec 15 15:02:43 GMT 2023 , Edited by admin on Fri Dec 15 15:02:43 GMT 2023
PRIMARY
RXCUI
235960
Created by admin on Fri Dec 15 15:02:43 GMT 2023 , Edited by admin on Fri Dec 15 15:02:43 GMT 2023
PRIMARY RxNorm
ECHA (EC/EINECS)
213-398-8
Created by admin on Fri Dec 15 15:02:43 GMT 2023 , Edited by admin on Fri Dec 15 15:02:43 GMT 2023
PRIMARY
MERCK INDEX
m5184
Created by admin on Fri Dec 15 15:02:43 GMT 2023 , Edited by admin on Fri Dec 15 15:02:43 GMT 2023
PRIMARY Merck Index
CAS
534-87-2
Created by admin on Fri Dec 15 15:02:43 GMT 2023 , Edited by admin on Fri Dec 15 15:02:43 GMT 2023
SUPERSEDED
FDA UNII
ZBI6Q5FH3S
Created by admin on Fri Dec 15 15:02:43 GMT 2023 , Edited by admin on Fri Dec 15 15:02:43 GMT 2023
PRIMARY
CAS
943-17-9
Created by admin on Fri Dec 15 15:02:43 GMT 2023 , Edited by admin on Fri Dec 15 15:02:43 GMT 2023
PRIMARY
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