OXYFEDRINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H23NO3
Molecular Weight	313.3908
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC(=CC=C1)C(=O)CCN[C@@H](C)[C@H](O)C2=CC=CC=C2

InChI

InChIKey=GDYUVHBMFVMBAF-LIRRHRJNSA-N

InChI=1S/C19H23NO3/c1-14(19(22)15-7-4-3-5-8-15)20-12-11-18(21)16-9-6-10-17(13-16)23-2/h3-10,13-14,19-20,22H,11-12H2,1-2H3/t14-,19-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C19H23NO3
Molecular Weight	313.3908
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1801897 | https://www.ncbi.nlm.nih.gov/pubmed/7437255

Oxyfedrine, an amino ketone derivative and partial agonist at beta receptors, has been shown to have potent antianginal properties and to increase coronary blood flow in normal and ischemic myocardial regions.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Adrenergic receptor beta 89 Target ID: CHEMBL2094118 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6095552 \| https://www.ncbi.nlm.nih.gov/pubmed/20326 \| http://www.drugsupdate.com/generic/view/377/Oxyfedrine	Partial Agonist 297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Angina pectoris 110 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1801897 https://www.ncbi.nlm.nih.gov/pubmed/4874592 https://www.ncbi.nlm.nih.gov/pubmed/4874592	Primary		Approved 8583	Ildamen Approved Use Angina pectoris
Myocardial infarction 125 Sources: https://www.ncbi.nlm.nih.gov/pubmed/359492	Primary		Approved 8583	Oxyfedrine Approved Use Myocardial infarction

Doses

Dose	Population	Adverse events
32 mg 3 times / day multiple, oral Higher than recommended Dose: 32 mg, 3 times / day Route: oral Route: multiple Dose: 32 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7437255/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7437255/	Disc. AE: Nausea, Vomiting... AEs leading to discontinuation/dose reduction: Nausea (3.3%) Vomiting (3.3%) Sources: https://pubmed.ncbi.nlm.nih.gov/7437255/
24 mg 3 times / day multiple, oral Recommended Dose: 24 mg, 3 times / day Route: oral Route: multiple Dose: 24 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7002181/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7002181/	Disc. AE: Taste loss, Myocardial infarction... AEs leading to discontinuation/dose reduction: Taste loss (4.3%) Myocardial infarction (4.3%) Sources: https://pubmed.ncbi.nlm.nih.gov/7002181/

AEs

AE	Significance	Dose	Population
Nausea	3.3% Disc. AE	32 mg 3 times / day multiple, oral Higher than recommended Dose: 32 mg, 3 times / day Route: oral Route: multiple Dose: 32 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7437255/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7437255/
Vomiting	3.3% Disc. AE	32 mg 3 times / day multiple, oral Higher than recommended Dose: 32 mg, 3 times / day Route: oral Route: multiple Dose: 32 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7437255/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7437255/
Myocardial infarction	4.3% Disc. AE	24 mg 3 times / day multiple, oral Recommended Dose: 24 mg, 3 times / day Route: oral Route: multiple Dose: 24 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7002181/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7002181/
Taste loss	4.3% Disc. AE	24 mg 3 times / day multiple, oral Recommended Dose: 24 mg, 3 times / day Route: oral Route: multiple Dose: 24 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7002181/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7002181/

PubMed

Title	Date	PubMed
Effects of oxyfedrine on regional myocardial blood flow in patients with coronary artery disease.	1991-12	1801897
Pulmonary and systemic circulatory effects and -adrenergic selectivity of hexoprenaline, salbutamol, oxyfedrine, and isoproterenol.	1971-07	5153847
[Stimulation of adrenergic beta-receptors in the heart of normal and reserpinized guinea pigs by oxyfedrine].	1969-09	5394533
[The management of angina pectoris using Ildamen, a new coronary- and cardiac-active substance, in a double-blind study].	1967-09-10	4874592

Patents

Sample Use Guides

In Vivo Use Guide

Oral Myocardial infarction, Angina pectoris Adult: 8-24 mg tid.

Route of Administration: Oral

In Vitro Use Guide

Oxyfedrine was tested in vitro against 471 strains of bacteria from two Gram positive and fourteen Gram negative genera. The minimum inhibitory concentration (MIC) of oxyfedrine was determined by agar dilution method, which ranged from 50-200 ug/ml in most of the strains, while some strains were inhibited at even lower concentrations.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 07:52:52 GMT 2025` Edited by `admin` on `Wed Apr 02 07:52:52 GMT 2025`
Record UNII	DWL616XF1K
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

OXYFEDRINE

Official Name

English

(-)-OXYFEDRINE

Preferred Name

English

3-(((.ALPHA.S,.BETA.R)-.BETA.-HYDROXY-.ALPHA.-METHYLPHENETHYL)AMINO)-3'-METHOXYPROPIOPHENONE

Common Name

English

OXYFEDRINE [MI]

Common Name

English

1-PROPANONE, 3-(((1S,2R)-2-HYDROXY-1-METHYL-2-PHENYLETHYL)AMINO)-1-(3-METHOXYPHENYL)-

Systematic Name

English

oxyfedrine [INN]

Common Name

English

Oxyfedrine [WHO-DD]

Common Name

English

Classification Tree Code System Code

WHO-ATC

C01DX53