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
Structure for Normethadone (DB11609)
- 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.
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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
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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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of adverse effects can be increased when Normethadone is combined with 1,2-Benzodiazepine. Acetazolamide The risk or severity of CNS depression can be increased when Acetazolamide is combined with Normethadone. Acetophenazine The risk or severity of hypotension and CNS depression can be increased when Acetophenazine is combined with Normethadone. Aclidinium The risk or severity of adverse effects can be increased when Aclidinium is combined with Normethadone. Agomelatine The risk or severity of CNS depression can be increased when Agomelatine is combined with Normethadone. - Food Interactions
- Avoid alcohol. Ingesting alcohol may cause additive CNS depressive effects.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Normethadone hydrochloride OIV53II16G 847-84-7 GYWUCVKLUKFJLC-UHFFFAOYSA-N - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Cophylac Normethadone hydrochloride (10 mg / mL) + Oxilofrine hydrochloride (20 mg / mL) Solution / drops Oral Bausch Health, Canada Inc. 1997-01-23 Not applicable Canada 
Cophylac Normethadone hydrochloride (10 mg / mL) + Oxilofrine hydrochloride (20 mg / mL) Solution / drops Oral Hoechst Canada Inc. 1957-12-31 1996-09-09 Canada Cophylac Drops Normethadone hydrochloride (10 mg / mL) + Oxilofrine hydrochloride (20 mg / mL) Solution / drops Oral Hoechst Roussel Canada Inc. 1993-12-31 1999-08-11 Canada
Categories
- ATC Codes
- R05DA06 — Normethadone
- Drug Categories
- Analgesics
- Antitussive Agents
- Central Nervous System Agents
- Central Nervous System Depressants
- Cough and Cold Preparations
- Ketones
- Narcotics
- Opioids
- Opium Alkaloids and Derivatives
- Peripheral Nervous System Agents
- Respiratory System Agents
- Sensory System Agents
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- 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
- Adcock JJ: Peripheral opioid receptors and the cough reflex. Respir Med. 1991 Jan;85 Suppl A:43-6. [Article]
- External Links
- KEGG Drug
- D07384
- PubChem Compound
- 10090
- PubChem Substance
- 347828004
- ChemSpider
- 9687
- 32009
- ChEBI
- 135242
- ChEMBL
- CHEMBL346331
- ZINC
- ZINC000001847280
- Wikipedia
- Normethadone
- FDA label
- Download (480 KB)
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Solution / drops Oral - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.00737 mg/mL ALOGPS logP 3.84 ALOGPS logP 4.59 Chemaxon logS -4.6 ALOGPS pKa (Strongest Acidic) 18.8 Chemaxon pKa (Strongest Basic) 8.83 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 20.31 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 92.85 m3·mol-1 Chemaxon Polarizability 34.67 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0002-0090000000-85344c3f6b560efafe92 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-0290000000-4716ca19cc84da7e5e66 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-05dj-6190000000-8c4238d9ac04019fa8d8 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-014u-0930000000-a45801e5fe0364a9cb82 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0900-9720000000-1492f1d37e71ac973179 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0296-1920000000-7eb8d050f76ebf903502 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 182.0333192 predictedDarkChem Lite v0.1.0 [M-H]- 171.60872 predictedDeepCCS 1.0 (2019) [M+H]+ 182.4812192 predictedDarkChem Lite v0.1.0 [M+H]+ 173.96672 predictedDeepCCS 1.0 (2019) [M+Na]+ 182.3990192 predictedDarkChem Lite v0.1.0 [M+Na]+ 180.05986 predictedDeepCCS 1.0 (2019)
Drug created at June 24, 2016 22:29 / Updated at February 21, 2021 18:53