Identification

Summary

Oxilofrine is an amphetamine used to treat a cough associated with inflamed mucosa.

Brand Names
Cophylac
Generic Name
Oxilofrine
DrugBank Accession Number
DB11610
Background

Oxilofrine is used in combination with Normethadone as an antitussive. It is currently marketed in Canada by Valeant under the tradename Cophylac.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 181.235
Monoisotopic: 181.110278727
Chemical Formula
C10H15NO2
Synonyms
  • 4-HMP
  • 4-hydroxyephedrine
  • Methyl synephrin
  • Methyl synephrine
  • Methylsympatol
  • Methylsynephrin
  • Methylsynephrine
  • Oxilofrine
  • Oxyephedrin
  • p-hydroxyephedrine
External IDs
  • J5.704E

Pharmacology

Indication

Used in combination with Normethadone as an antitussive Label.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Oxilofrine is a sympathomimetic which increases adrenergic activity 1.

Mechanism of action

Oxilofrine is likely helps to treat cough by stimulating α1 adrenergic receptors resulting in vasoconstriction. This would serve to reduce secretion of mucus into the airway and lessen the stimulus to cough.

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
  • Avoid alcohol. Ingesting alcohol may cause additive CNS depressive effects.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Oxilofrine hydrochloride3O9694M5EO942-51-8ICBZSKCTKKUQSY-YUWZRIFDSA-N
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
CophylacOxilofrine hydrochloride (20 mg / mL) + Normethadone hydrochloride (10 mg / mL)Solution / dropsOralHoechst Canada Inc.1957-12-311996-09-09Canada flag
CophylacOxilofrine hydrochloride (20 mg / mL) + Normethadone hydrochloride (10 mg / mL)Solution / dropsOralBausch Health, Canada Inc.1997-01-23Not applicableCanada flag
Cophylac DropsOxilofrine hydrochloride (20 mg / mL) + Normethadone hydrochloride (10 mg / mL)Solution / dropsOralHoechst Roussel Canada Inc.1993-12-311999-08-11Canada flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenylpropanes
Direct Parent
Phenylpropanes
Alternative Parents
Aralkylamines / 1-hydroxy-2-unsubstituted benzenoids / Secondary alcohols / 1,2-aminoalcohols / Dialkylamines / Organopnictogen compounds / Hydrocarbon derivatives / Aromatic alcohols
Substituents
1,2-aminoalcohol / 1-hydroxy-2-unsubstituted benzenoid / Alcohol / Amine / Aralkylamine / Aromatic alcohol / Aromatic homomonocyclic compound / Hydrocarbon derivative / Organic nitrogen compound / Organic oxygen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
F49638UBDR
CAS number
365-26-4
InChI Key
OXFGTKPPFSCSMA-XVKPBYJWSA-N
InChI
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
IUPAC Name
4-[(1R,2S)-1-hydroxy-2-(methylamino)propyl]phenol
SMILES
[H][C@@](C)(NC)[C@]([H])(O)C1=CC=C(O)C=C1

References

General References
  1. KEGG: Oxilofrine [Link]
KEGG Drug
D08314
PubChem Compound
688009
PubChem Substance
347828005
ChemSpider
599505
RxNav
32639
ChEBI
134822
ChEMBL
CHEMBL1160695
ZINC
ZINC000000056399
Wikipedia
Oxilofrine
FDA label
Download (480 KB)
MSDS
Download (391 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Solution / dropsOral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)207MSDS
water solubilityPartly miscibleMSDS
Predicted Properties
PropertyValueSource
Water Solubility12.2 mg/mLALOGPS
logP-0.13ALOGPS
logP0.28ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)9.19ChemAxon
pKa (Strongest Basic)9.8ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area52.49 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity51.67 m3·mol-1ChemAxon
Polarizability19.98 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Drug created at June 24, 2016 22:52 / Updated at February 21, 2021 18:53