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Details

Stereochemistry RACEMIC
Molecular Formula C10H15NO2
Molecular Weight 181.2316
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OXILOFRINE

SMILES

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

InChI

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

HIDE SMILES / InChI
Molecular Formula C10H15NO2
Molecular Weight 181.2316
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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

CNS Active
3913
Curator's Comment: Oxilofrine is a sympathomimetic used to treat hypotensive states, with actions similar to those of ephedrine.

Originator

Liljestrand, G.|Linde, P.
2
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

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
Activator
1430
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Not Provided
504
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
Not Provided
504
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
Not Provided
504
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
Not Provided
504
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
[Effects of oxilofrine on the release and storage of noradrenaline in cardiac sections of the rat (author's transl)].
1980
Pharmacokinetic parameters and haemodynamic actions of midodrine in young volunteers.
1993 Jun
Pharmacology of stimulants prohibited by the World Anti-Doping Agency (WADA).
2008 Jun
Patents

Patents

20050020834
4
20050176790
4
US1877756
2

Sample Use Guides

In Vivo Use Guide
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%.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:59:55 GMT 2023
Edited
by admin
on Fri Dec 15 15:59:55 GMT 2023
Record UNII
F49638UBDR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OXILOFRINE
INN   WHO-DD  
INN  
Official Name English
METHYL SYNEPHRINE
Common Name English
METHYL SYNEPHRIN
Common Name English
(±)-P-HYDROXYEPHEDRINE
Common Name English
METHYLSYNEPHRINE
Common Name English
EDORNAT
Brand Name English
P-HYDROXYEPHEDRINE
MI  
Common Name English
SUPRIFEN
Brand Name English
P-HYDROXYEPHEDRINE [MI]
Common Name English
P-HYDROXY-.ALPHA.-(1-(METHYLAMINO)ETHYL)BENZYL ALCOHOL
Common Name English
REL-(.ALPHA.S)-4-HYDROXY-.ALPHA.-((1R)-1-(METHYLAMINO)ETHYL)BENZENEMETHANOL
Common Name English
METHYLSYMPATOL
Brand Name English
BENZENEMETHANOL, 4-HYDROXY-.ALPHA.-((1R)-1-(METHYLAMINO)ETHYL)-, (.ALPHA.S)-REL-
Common Name English
.ALPHA.-(1-METHYLAMINOETHYL)-P-HYDROXYBENZYL ALCOHOL
Common Name English
METHYLSYNEPHRIN
Common Name English
4-HYDROXYEPHEDRINE
Common Name English
1-(4-HYDROXYPHENYL)-2-METHYLAMINOPROPANOL
Systematic Name English
ERYTHRO-P-HYDROXY-.ALPHA.-(1-(METHYLAMINO)ETHYL)BENZYL ALCOHOL
Common Name English
oxilofrine [INN]
Common Name English
Oxilofrine [WHO-DD]
Common Name English
J5.704E
Code English
CARNIGEN
Brand Name English
OXYEPHEDRIN
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29747
Created by admin on Fri Dec 15 15:59:55 GMT 2023 , Edited by admin on Fri Dec 15 15:59:55 GMT 2023
DSLD 3114 (Number of products:49)
Created by admin on Fri Dec 15 15:59:55 GMT 2023 , Edited by admin on Fri Dec 15 15:59:55 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C74102
Created by admin on Fri Dec 15 15:59:55 GMT 2023 , Edited by admin on Fri Dec 15 15:59:55 GMT 2023
PRIMARY
DRUG CENTRAL
3286
Created by admin on Fri Dec 15 15:59:55 GMT 2023 , Edited by admin on Fri Dec 15 15:59:55 GMT 2023
PRIMARY
ChEMBL
CHEMBL30400
Created by admin on Fri Dec 15 15:59:55 GMT 2023 , Edited by admin on Fri Dec 15 15:59:55 GMT 2023
PRIMARY
RXCUI
32639
Created by admin on Fri Dec 15 15:59:55 GMT 2023 , Edited by admin on Fri Dec 15 15:59:55 GMT 2023
PRIMARY RxNorm
SMS_ID
100000091771
Created by admin on Fri Dec 15 15:59:55 GMT 2023 , Edited by admin on Fri Dec 15 15:59:55 GMT 2023
PRIMARY
ECHA (EC/EINECS)
206-672-3
Created by admin on Fri Dec 15 15:59:55 GMT 2023 , Edited by admin on Fri Dec 15 15:59:55 GMT 2023
PRIMARY
WIKIPEDIA
OXILOFRINE
Created by admin on Fri Dec 15 15:59:55 GMT 2023 , Edited by admin on Fri Dec 15 15:59:55 GMT 2023
PRIMARY
EVMPD
SUB09529MIG
Created by admin on Fri Dec 15 15:59:55 GMT 2023 , Edited by admin on Fri Dec 15 15:59:55 GMT 2023
PRIMARY
MERCK INDEX
m6133
Created by admin on Fri Dec 15 15:59:55 GMT 2023 , Edited by admin on Fri Dec 15 15:59:55 GMT 2023
PRIMARY Merck Index
PUBCHEM
688009
Created by admin on Fri Dec 15 15:59:55 GMT 2023 , Edited by admin on Fri Dec 15 15:59:55 GMT 2023
PRIMARY
INN
4665
Created by admin on Fri Dec 15 15:59:55 GMT 2023 , Edited by admin on Fri Dec 15 15:59:55 GMT 2023
PRIMARY
CAS
365-26-4
Created by admin on Fri Dec 15 15:59:55 GMT 2023 , Edited by admin on Fri Dec 15 15:59:55 GMT 2023
PRIMARY
FDA UNII
F49638UBDR
Created by admin on Fri Dec 15 15:59:55 GMT 2023 , Edited by admin on Fri Dec 15 15:59:55 GMT 2023
PRIMARY
EPA CompTox
DTXSID1091557
Created by admin on Fri Dec 15 15:59:55 GMT 2023 , Edited by admin on Fri Dec 15 15:59:55 GMT 2023
PRIMARY
Related Record Type Details
Structure of OXILOFRINE HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of methyl-MA
PARENT -> METABOLITE
MINOR
Related Record Type Details
Structure of OXILOFRINE
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