OXILOFRINE HYDROCHLORIDE

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 Search

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

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

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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27062112
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Beta-1 adrenergic receptor 158 Target ID: CHEMBL213 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27062112	Agonist 2678
regulation of norepinephrine secretion 9 Target ID: GO:0014061 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7191269	Activator 1430

Conditions

Condition	Modality	Highest Phase	Product
Low blood pressure 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27062112	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.
Asthma 241 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27062112	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.
Cough 106 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27062112	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.
Pain 614 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27062112	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

Title	Date	PubMed
[Effects of oxilofrine on the release and storage of noradrenaline in cardiac sections of the rat (author's transl)].	1980	7191269
Clinical pharmacokinetics after a single oral dose of oxilofrine.	1988	3229871
Cardiovascular parameters and catecholamines in volunteers during passive orthostasis. Influence of antihypotensive drugs.	1992 May	1530677
Pharmacokinetic parameters and haemodynamic actions of midodrine in young volunteers.	1993 Jun	7690382
Pharmacology of stimulants prohibited by the World Anti-Doping Agency (WADA).	2008 Jun	18500382
Efficacy of treatments for orthostatic hypotension: a systematic review.	2012 Sep	22591985
A cocktail of synthetic stimulants found in a dietary supplement associated with serious adverse events.	2014 Jun	24802503
Pharmaceutical doses of the banned stimulant oxilofrine found in dietary supplements sold in the USA.	2017 Jan	27062112

Patents

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 15:11:23 GMT 2023` Edited by `admin` on `Fri Dec 15 15:11:23 GMT 2023`
Record UNII	3O9694M5EO
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

OXILOFRINE HYDROCHLORIDE

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

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