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Details

Stereochemistry RACEMIC
Molecular Formula C10H15NO2.ClH
Molecular Weight 217.693
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OXILOFRINE HYDROCHLORIDE

SMILES

Cl.CN[C@@H](C)[C@H](O)C1=CC=C(O)C=C1

InChI

InChIKey=ICBZSKCTKKUQSY-YUWZRIFDSA-N
InChI=1S/C10H15NO2.ClH/c1-7(11-2)10(13)8-3-5-9(12)6-4-8;/h3-7,10-13H,1-2H3;1H/t7-,10-;/m0./s1

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/18500382

Oxilofrine is a sympathomimetic used to treat hypotensive states, with cardiac stimulatory effects similar to those of ephedrine. It has never been approved for use in the USA as a prescription drug or as a dietary supplement. Oxilofrine has been found (1) to act predominantly as a beta1 agonist increasing the speed and force of heart muscle contraction (inotropic effects), specifically, increasing left ventricular ejection fraction and stroke volume; (2) to increase blood pressure; (3) to have variable effects on heart rate; and (4) to potentially increase oxygen uptake by the lungs.

CNS Activity

Curator's Comment: Oxilofrine is a sympathomimetic used to treat hypotensive states, with actions similar to those of ephedrine.

Originator

Curator's Comment: Original source: G. Liljestrand, P. Linde. Die Wirkung von Oxy-ephedrinen auf Gaswechsel und Kreislauf beim Menschen. Arch. Inter. Pharmacodyn. Ther. 1933, 45, 318.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
OXILOFRINE

Approved Use

Oxilofrine has been used in a variety of medications to treat low blood pressure, to manage asthma exacerbations, to suppress coughing, and to enhance cardiac function during anesthesia.
Palliative
OXILOFRINE

Approved Use

Oxilofrine has been used in a variety of medications to treat low blood pressure, to manage asthma exacerbations, to suppress coughing, and to enhance cardiac function during anesthesia.
Primary
OXILOFRINE

Approved Use

Oxilofrine has been used in a variety of medications to treat low blood pressure, to manage asthma exacerbations, to suppress coughing, and to enhance cardiac function during anesthesia.
Secondary
OXILOFRINE

Approved Use

Oxilofrine has been used in a variety of medications to treat low blood pressure, to manage asthma exacerbations, to suppress coughing, and to enhance cardiac function during anesthesia.
PubMed

PubMed

TitleDatePubMed
Cardiovascular parameters and catecholamines in volunteers during passive orthostasis. Influence of antihypotensive drugs.
1992 May
Pharmacokinetic parameters and haemodynamic actions of midodrine in young volunteers.
1993 Jun
Patents

Sample Use Guides

The usual adult dose is 32 mg.
Route of Administration: Oral
In Vitro Use Guide
Experiments in vitro have shown oxilofrine to release noradrenaline from rat cardiac ventricular sections. This effect sets in at a concentration of 10^-5 mol/l and reaches the 30% level at 5*10^-5 mol/l. The inhibition of noradrenaline storage is still more pronounced. At 5*10^-5 mol/l the inhibition is 60%.
Name Type Language
OXILOFRINE HYDROCHLORIDE
WHO-DD  
Common Name English
SUPRIFEN HYDROCHLORIDE
Brand Name English
BENZENEMETHANOL, 4-HYDROXY-.ALPHA.-(1-(METHYLAMINO)ETHYL)-, HYDROCHLORIDE, (R*,S*)-
Common Name English
P-HYDROXYEPHEDRINE HYDROCHLORIDE
Common Name English
4-HYDROXYEPHEDRINE HYDROCHLORIDE
MI  
Common Name English
4-HYDROXYEPHEDRINE HYDROCHLORIDE [MI]
Common Name English
Oxilofrine hydrochloride [WHO-DD]
Common Name English
OXILOFRINE HCL
Common Name English
HYDROXYEPHEDRINE HYDROCHLORIDE, P-
Common Name English
Code System Code Type Description
SMS_ID
100000085488
Created by admin on Fri Dec 15 15:11:23 GMT 2023 , Edited by admin on Fri Dec 15 15:11:23 GMT 2023
PRIMARY
DRUG BANK
DBSALT001920
Created by admin on Fri Dec 15 15:11:23 GMT 2023 , Edited by admin on Fri Dec 15 15:11:23 GMT 2023
PRIMARY
PUBCHEM
12625680
Created by admin on Fri Dec 15 15:11:23 GMT 2023 , Edited by admin on Fri Dec 15 15:11:23 GMT 2023
PRIMARY
FDA UNII
3O9694M5EO
Created by admin on Fri Dec 15 15:11:23 GMT 2023 , Edited by admin on Fri Dec 15 15:11:23 GMT 2023
PRIMARY
CAS
942-51-8
Created by admin on Fri Dec 15 15:11:23 GMT 2023 , Edited by admin on Fri Dec 15 15:11:23 GMT 2023
PRIMARY
EVMPD
SUB03572MIG
Created by admin on Fri Dec 15 15:11:23 GMT 2023 , Edited by admin on Fri Dec 15 15:11:23 GMT 2023
PRIMARY
EPA CompTox
DTXSID90273983
Created by admin on Fri Dec 15 15:11:23 GMT 2023 , Edited by admin on Fri Dec 15 15:11:23 GMT 2023
PRIMARY
ECHA (EC/EINECS)
213-392-5
Created by admin on Fri Dec 15 15:11:23 GMT 2023 , Edited by admin on Fri Dec 15 15:11:23 GMT 2023
PRIMARY
RXCUI
236554
Created by admin on Fri Dec 15 15:11:23 GMT 2023 , Edited by admin on Fri Dec 15 15:11:23 GMT 2023
PRIMARY RxNorm