Normethadone

Identification

Summary

Normethadone is an opioid antitussive used to treat a cough associated with inflamed mucosa.

Brand Names
Cophylac
Generic Name
Normethadone
DrugBank Accession Number
DB11609
Background

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

Type
Small Molecule
Groups
Approved, Illicit
Structure
Thumb
Weight
Average: 295.426
Monoisotopic: 295.193614429
Chemical Formula
C20H25NO
Synonyms
  • 6-dimethylamino-4,4-diphenyl-3-hexanone
  • Desmethylmethadone
  • Isomethadone I
  • Normethadone
External IDs
  • Hoechst 10582
  • IDS-NN-007
  • J5.915C
  • NSC-19598

Pharmacology

Indication

For use in the treatment of cough when other less potent treatments have failed Label.

Pharmacology
Accelerate your drug discovery research with the industry’s only fully connected ADMET dataset, ideal for:
Machine Learning
Data Science
Drug Discovery
Accelerate your drug discovery research with our fully connected ADMET dataset
Learn more
Contraindications & Blackbox Warnings
Contraindications
Contraindications & Blackbox Warnings
With our commercial data, access important information on dangerous risks, contraindications, and adverse effects.
Learn more
Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects
Learn more
Pharmacodynamics

Normethadone is an opioid which suppresses coughing by central and peripheral mechanisms Label 1.

Mechanism of action

Normethadone activates central opioid receptors in the medulla to supress the cough reflex 1. It also likely activates peripheral opioid receptors to inhibit signalling by irritant receptors of the airway.

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
Medicalerrors
Reduce medical errors
and improve treatment outcomes with our comprehensive & structured data on drug adverse effects.
Learn more
Reduce medical errors & improve treatment outcomes with our adverse effects data
Learn more
Toxicity

The toxic effects of normethadone are similar to those of other opioids. It can produce respiratory depression, depression of central nervous system function, and constipation Label.

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.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when Normethadone is combined with 1,2-Benzodiazepine.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Normethadone.
AcetophenazineThe risk or severity of hypotension and CNS depression can be increased when Acetophenazine is combined with Normethadone.
AclidiniumThe risk or severity of adverse effects can be increased when Normethadone is combined with Aclidinium.
AgomelatineThe risk or severity of adverse effects can be increased when Agomelatine is combined with Normethadone.
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Normethadone.
AlimemazineThe risk or severity of hypotension and CNS depression can be increased when Alimemazine is combined with Normethadone.
AlloinThe therapeutic efficacy of Alloin can be decreased when used in combination with Normethadone.
AlmotriptanThe risk or severity of adverse effects can be increased when Almotriptan is combined with Normethadone.
AlosetronThe risk or severity of adverse effects can be increased when Alosetron is combined with Normethadone.
Interactions
Improve patient outcomes
Build effective decision support tools with the industry’s most comprehensive drug-drug interaction checker.
Learn more
Food Interactions
  • Avoid alcohol. Ingesting alcohol may cause additive CNS depressive effects.

Products

Products
Comprehensive & structured drug product info
From application numbers to product codes, connect different identifiers through our commercial datasets.
Learn more
Easily connect various identifiers back to our datasets
Learn more
Product Ingredients
IngredientUNIICASInChI Key
Normethadone hydrochlorideOIV53II16G847-84-7GYWUCVKLUKFJLC-UHFFFAOYSA-N
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
CophylacNormethadone hydrochloride (10 mg / mL) + Oxilofrine hydrochloride (20 mg / mL)Solution / dropsOralHoechst Canada Inc.1957-12-311996-09-09Canada flag
CophylacNormethadone hydrochloride (10 mg / mL) + Oxilofrine hydrochloride (20 mg / mL)Solution / dropsOralBausch Health, Canada Inc.1997-01-23Not applicableCanada flag
Cophylac DropsNormethadone hydrochloride (10 mg / mL) + Oxilofrine hydrochloride (20 mg / mL)Solution / dropsOralHoechst Roussel Canada Inc.1993-12-311999-08-11Canada flag

Categories

ATC Codes
R05DA06 — Normethadone
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Diphenylmethanes
Direct Parent
Diphenylmethanes
Alternative Parents
Aralkylamines / Gamma-amino ketones / Trialkylamines / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
Amine / Aralkylamine / Aromatic homomonocyclic compound / Carbonyl group / Diphenylmethane / Gamma-aminoketone / Hydrocarbon derivative / Ketone / Organic nitrogen compound / Organic oxide
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
KR2L2A68XL
CAS number
467-85-6
InChI Key
WCJFBSYALHQBSK-UHFFFAOYSA-N
InChI
InChI=1S/C20H25NO/c1-4-19(22)20(15-16-21(2)3,17-11-7-5-8-12-17)18-13-9-6-10-14-18/h5-14H,4,15-16H2,1-3H3
IUPAC Name
6-(dimethylamino)-4,4-diphenylhexan-3-one
SMILES
CCC(=O)C(CCN(C)C)(C1=CC=CC=C1)C1=CC=CC=C1

References

General References
  1. Adcock JJ: Peripheral opioid receptors and the cough reflex. Respir Med. 1991 Jan;85 Suppl A:43-6. [Article]
KEGG Drug
D07384
PubChem Compound
10090
PubChem Substance
347828004
ChemSpider
9687
RxNav
32009
ChEBI
135242
ChEMBL
CHEMBL346331
ZINC
ZINC000001847280
Wikipedia
Normethadone
FDA label
Download (480 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
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00737 mg/mLALOGPS
logP3.84ALOGPS
logP4.59ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)18.8ChemAxon
pKa (Strongest Basic)8.83ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area20.31 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity92.85 m3·mol-1ChemAxon
Polarizability34.67 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
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 on June 24, 2016 22:29 / Updated on February 21, 2021 18:53