Dextromethorphan
Identification
- Name
- Dextromethorphan
- Accession Number
- DB00514
- Description
Dextromethorphan is a levorphanol derivative and codeine analog commonly used as a cough suppressant and also a drug of abuse.11 Although similar in structure to other opioids, it has minimal interaction with opioid receptors.11
Dextromethorphan was granted FDA approval before 3 December 1957.11,16
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Dextromethorphan (DB00514)
- Weight
- Average: 271.404
Monoisotopic: 271.193614429 - Chemical Formula
- C18H25NO
- Synonyms
- (+)-dextromethorphan
- D-methorphan
- delta-Methorphan
- Dex
- Dextromethorfan
- Dextromethorphan
- Dextrométhorphane
- Dextromethorphanum
- Dextrometorfano
- DM
- External IDs
- BA 2666
Pharmacology
Accelerate your drug discovery research with the industry’s only fully connected ADMET dataset, ideal for:Accelerate your drug discovery research with our fully connected ADMET dataset- Indication
Dextromethorphan is indicated in combination with brompheniramine and pseudoephedrine in the treatment of coughs and upper respiratory symptoms associated with allergies or the common cold.13 Dextromethorphan is also used in combination with guaifenesin as an over the counter product to relieve a cough.14 Dextromethorpahn in combination with quinidine is indicated in the treatment of pseudobulbar affect.12
- Associated Conditions
- Allergic cough
- Common Cold
- Common Cold/Flu
- Cough caused by Common Cold
- Coughing
- Coughing caused by Allergies
- Coughing caused by Bronchitis
- Coughing caused by Flu caused by Influenza
- Fever
- Flu caused by Influenza
- Headache
- Irritative cough
- Itching of the nose
- Itching of the throat
- Nasal Congestion
- Pseudobulbar affect
- Rhinorrhoea
- Sneezing
- Upper respiratory symptoms
- Watery itchy eyes
- Associated Therapies
- Contraindications & Blackbox Warnings
Contraindications & Blackbox WarningsWith our commercial data, access important information on dangerous risks, contraindications, and adverse effects.Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects- Pharmacodynamics
Dextromethorphan is an opioid-like molecule indicated in combination with other medication in the treatment of coughs and pseudobulbar affect.13,14,12 It has a moderate therapeutic window, as intoxication can occur at higher doses.10 Dextromethorphan has a moderate duration of action.12 Patients should be counselled regarding the risk of intoxication.10
- Mechanism of action
Dextromethorphan is an agonist of NMDA and sigma-1 receptors.12 It is also an antagonist of α3/β4 nicotinic receptors.[A10589] However, the mechanism by which dextromethorphan's receptor agonism and antagonism translates to a clinical effect is not well understood.9
Target Actions Organism ASigma non-opioid intracellular receptor 1 agonistHumans AHCG20471, isoform CRA_c agonistHumans UNeuronal acetylcholine receptor subunit alpha-2 antagonistHumans AGlutamate receptor ionotropic, NMDA 3A antagonistHumans USodium-dependent serotonin transporter inhibitorHumans UMembrane-associated progesterone receptor component 1 binderHumans UNeuronal acetylcholine receptor subunit alpha-3 antagonistHumans UNeuronal acetylcholine receptor subunit alpha-4 antagonistHumans UNeuronal acetylcholine receptor subunit beta-4 antagonistHumans UNeuronal acetylcholine receptor subunit beta-2 antagonistHumans UNeuronal acetylcholine receptor subunit alpha-7 antagonistHumans UMu-type opioid receptor agonistHumans UDelta-type opioid receptor agonistHumans UKappa-type opioid receptor agonistHumans UNADPH oxidase inhibitorHumans USodium-dependent noradrenaline transporter inhibitorHumans - Absorption
A 30mg oral dose of dextromethorphan reaches a Cmax of 2.9 ng/mL, with a Tmax of 2.86 h, and an AUC of 17.8 ng*h/mL.7
- Volume of distribution
The volume of distribution of dextromethorphan is 5-6.7L/kg.8
- Protein binding
Dextromethorphan is 60-70% protein bound in serum.12
- Metabolism
Dextromethorphan can be N-demethylated to 3-methoxymorphinan by CYP3A4, CYP2D6, and CYP2C9 or O-demethylated to dextrorphan by CYP2D6 and CYP2C9.6 Dextrorphan is N-demethylated by CYP3A4 and CYP2D6, while 3-methoxymorphinan is O-demethylated by CYP2D6.6 Both are metabolized to form 3-hydroxymorphinan.6 Dextrorphan and 3-hydroxymorphinan are both O-glucuronidated or O-sulfated.6
Hover over products below to view reaction partners
- Route of elimination
- Not Available
- Half-life
Dextromethorphan has a half life of 3-30 hours.8
- Clearance
- Not Available
- Adverse Effects
Reduce medical errorsand improve treatment outcomes with our comprehensive & structured data on drug adverse effects.Reduce medical errors & improve treatment outcomes with our adverse effects data- Toxicity
A dextromethorphan overdose may present as nausea, vomiting, stupor, coma, respiratory depression, seizures, tachycardia, hyperexcitability, toxic psychosis, ataxia, nystagmus, dystonia, blurred vision, changes in muscle reflexes, and serotonin syndrome.12 Overdose should be managed through symptomatic and supportive measures.12
- Affected organisms
- Humans and other mammals
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
Interacting Gene/Enzyme Allele name Genotype(s) Defining Change(s) Type(s) Description Details Cytochrome P450 2D6 CYP2D6*4 (A;A) A Allele, homozygote Effect Directly Studied Patients with this genotype have reduced metabolism of dextromethorphan. Details Cytochrome P450 2D6 CYP2D6*6 (-;-) T deletion, homozygote Effect Directly Studied Patients with this genotype have reduced metabolism of dextromethorphan. Details Cytochrome P450 2D6 CYP2D6*3 Not Available C allele Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*5 Not Available Whole-gene deletion Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*7 Not Available 2935A>C Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*8 Not Available 1758G>T Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*11 Not Available 883G>C Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*12 Not Available 124G>A Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*13 Not Available CYP2D7/2D6 hybrid gene structure Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*14A Not Available 1758G>A Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*15 Not Available 137insT, 137_138insT Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*19 Not Available 2539_2542delAACT Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*20 Not Available 1973_1974insG Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*21 Not Available 2573insC Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*31 Not Available -1770G>A / -1584C>G … show all Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*36 Not Available 100C>T / -1426C>T … show all Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*38 Not Available 2587_2590delGACT Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*40 Not Available 1863_1864ins(TTT CGC CCC)2 Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*42 Not Available 3259_3260insGT Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*44 Not Available 2950G>C Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*47 Not Available 100C>T / -1426C>T … show all Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*51 Not Available -1584C>G / -1235A>G … show all Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*56 Not Available 3201C>T Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*57 Not Available 100C>T / 310G>T … show all Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*62 Not Available 4044C>T Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*68A Not Available -1426C>T / -1235A>G … show all Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*68B Not Available Similar but not identical switch region compared to CYP2D6*68A. Found in tandem arrangement with CYP2D6*4. Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*69 Not Available 2988G>A / -1426C>T … show all Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*92 Not Available 1995delC Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*100 Not Available -1426C>T / -1235A>G … show all Effect Inferred Poor drug metabolizer, lower dose requirements Details Cytochrome P450 2D6 CYP2D6*101 Not Available -1426C>T / -1235A>G … show all Effect Inferred Poor drug metabolizer, lower dose requirements Details
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 softwareAbametapir The serum concentration of Dextromethorphan can be increased when it is combined with Abametapir. Abatacept The metabolism of Dextromethorphan can be increased when combined with Abatacept. Abiraterone The metabolism of Dextromethorphan can be decreased when combined with Abiraterone. Acalabrutinib The metabolism of Dextromethorphan can be decreased when combined with Acalabrutinib. Acebutolol The metabolism of Dextromethorphan can be decreased when combined with Acebutolol. Acenocoumarol The metabolism of Acenocoumarol can be decreased when combined with Dextromethorphan. Acetazolamide The risk or severity of adverse effects can be increased when Dextromethorphan is combined with Acetazolamide. Acetohexamide The metabolism of Dextromethorphan can be decreased when combined with Acetohexamide. Acetophenazine The risk or severity of adverse effects can be increased when Dextromethorphan is combined with Acetophenazine. Acetyl sulfisoxazole The metabolism of Dextromethorphan can be decreased when combined with Acetyl sulfisoxazole. 
Improve patient outcomesBuild effective decision support tools with the industry’s most comprehensive drug-drug interaction checker.Learn more - Food Interactions
- Take with or without food. The absorption is unaffected by food.
Products
Comprehensive & structured drug product infoFrom application numbers to product codes, connect different identifiers through our commercial datasets.Easily connect various identifiers back to our datasets- Product Ingredients
Ingredient UNII CAS InChI Key Dextromethorphan hydriodide 086F8ZEM77 7487-74-3 RWSHVMCJJPXQSP-URVXVIKDSA-N Dextromethorphan hydrobromide Z0CG3115FG 125-69-9 MISZALMBODQYFT-URVXVIKDSA-N Dextromethorphan hydrobromide monohydrate 9D2RTI9KYH 6700-34-1 STTADZBLEUMJRG-IKNOHUQMSA-N Dextromethorphan hydrochloride 351KFH969D 18609-21-7 SNDDIRAXSDUVKW-URVXVIKDSA-N - Active Moieties
Name Kind UNII CAS InChI Key Dextrorphan prodrug 04B7QNO9WS 125-73-5 JAQUASYNZVUNQP-PVAVHDDUSA-N - Product Images
- International/Other Brands
- Benylin DM (McNeil) / Romilar (Bayer) / Triaminic (Novartis) / Vicks Formula 44 (Procter & Gamble)
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image 12 Hour Cough Relief Suspension 30 mg/5mL Oral Western Family Foods 2013-07-03 2017-04-01 US 
12 Hour Cough Relief Suspension 30 mg/5mL Oral Western Family Foods 2012-09-14 2017-05-01 US 7 Select Cough DM Suspension 30 mg/5mL Oral 7 Eleven 2014-09-05 2016-10-01 US Adult Cough Relief DM Liquid 30 mg/10mL Oral Safeway, Inc. 2014-06-30 Not applicable US Adult Honey Works Syrup Oral Lifelab Health Llc 2018-10-09 Not applicable Canada 
Adult Long Lasting-Cough Relief Capsule 15 mg/1 Oral Chain Drug Consortium 2013-05-22 Not applicable US Adult Tussin Cough Liquid 30 mg/10mL Oral Western Family Foods 1992-09-11 2017-08-09 US Adult Tussin Cough Gels Capsule, gelatin coated 15 mg/1 Oral Army + Air Force Exchange Service 2006-04-24 2018-08-27 US Adult Wal Tussin Cough Long Acting Solution 30 mg/10mL Oral Walgreen 2004-09-03 Not applicable US Balminil DM Syrup Oral TEVA Canada Limited 1979-12-31 2020-04-22 Canada - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image 7 Select Day Time Relief Dextromethorphan hydrobromide monohydrate (10 mg/15mL) + Acetaminophen (325 mg/15mL) + Phenylephrine hydrochloride (5 mg/15mL) Solution Oral 7-Eleven 2014-08-05 2020-10-31 US 7 Select Day Time Relief Dextromethorphan hydrobromide monohydrate (10 mg/1) + Acetaminophen (325 mg/1) + Phenylephrine hydrochloride (5 mg/1) Capsule, liquid filled Oral 7-Eleven 2014-04-22 2020-01-31 US 7 Select Maximum Strength Dextromethorphan hydrobromide monohydrate (20 mg/20mL) + Guaifenesin (400 mg/20mL) Solution Oral 7-Eleven 2019-03-25 Not applicable US 7 Select Night Time Relief Dextromethorphan hydrobromide monohydrate (15 mg/1) + Acetaminophen (325 mg/1) + Doxylamine succinate (6.25 mg/1) Capsule, liquid filled Oral 7-Eleven 2014-04-17 2020-07-31 US 7 Select Night Time Relief Dextromethorphan hydrobromide monohydrate (30 mg/30mL) + Acetaminophen (650 mg/30mL) + Doxylamine succinate (12.5 mg/30mL) Solution Oral 7-Eleven 2014-08-05 2021-03-31 US 7 select Tussin DM Dextromethorphan hydrobromide monohydrate (20 mg/10mL) + Guaifenesin (200 mg/10mL) Solution Oral 7-Eleven 2016-05-31 2021-06-30 US A.M. Cold Relief Formula Dextromethorphan hydrobromide (15 mg) + Acetaminophen (325 mg) + Pseudoephedrine hydrochloride (30 mg) Capsule Oral Ivax Pharmaceuticals Incorporated Not applicable Not applicable Canada Abatuss Dmx Dextromethorphan hydrobromide monohydrate (15 mg/5mL) + Dexchlorpheniramine maleate (1 mg/5mL) + Pseudoephedrine hydrochloride (30 mg/5mL) Liquid Oral KRAMER NOVIS 2014-05-25 Not applicable US AccuHist PDX Dextromethorphan hydrobromide monohydrate (2.5 mg/1mL) + Chlorpheniramine maleate (1 mg/1mL) + Phenylephrine hydrochloride (2.5 mg/1mL) Solution Oral Tiber Laboratories, LLC 2010-01-25 2013-04-30 US Acetaflu Cough and Chest Congestion Dextromethorphan hydrobromide monohydrate (20 mg/5g) + Guaifenesin (400 mg/5g) Powder Oral Advanced Pharmaceutical Services, Inc. Dba Affordable Quality Pharmaceuticals 2020-08-31 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Atuss DS Tannate Suspension Dextromethorphan hydrobromide monohydrate (30 mg/5mL) + Chlorpheniramine maleate (4 mg/5mL) + Pseudoephedrine hydrochloride (30 mg/5mL) Suspension Oral Atley Pharmaceuticals 2006-11-21 Not applicable US BPM Mal Phenyleph HCl DM HBr Dextromethorphan hydrobromide monohydrate (20 mg/5mL) + Brompheniramine maleate (4 mg/5mL) + Phenylephrine hydrochloride (10 mg/5mL) Liquid Oral River's Edge Pharmaceuticals, LLC 2010-01-18 2012-01-31 US Brom Mal Phenyl HCl Dex HBr Dextromethorphan hydrobromide monohydrate (15 mg/5mL) + Brompheniramine maleate (4 mg/5mL) + Phenylephrine hydrochloride (7.5 mg/5mL) Liquid Oral River's Edge Pharmaceuticals, LLC 2010-02-10 2012-02-29 US Bromdex D Dextromethorphan hydrobromide monohydrate (30 mg/5mL) + Brompheniramine maleate (3 mg/5mL) + Pseudoephedrine hydrochloride (50 mg/5mL) Syrup Oral Breckenridge Pharmaceutical, Inc. 2009-07-21 2011-05-31 US Bromhist PDX Dextromethorphan hydrobromide monohydrate (5 mg/5mL) + Brompheniramine maleate (2 mg/5mL) + Guaifenesin (50 mg/5mL) + Phenylephrine hydrochloride (5 mg/5mL) Syrup Oral Cypress Pharmaceutical, Inc 2006-04-28 2011-08-26 US Brompheniramine Maleate, Pseudoephedrine Hydrochloride, Dextromethorphan Hydrobromide Dextromethorphan hydrobromide monohydrate (20 mg/5mL) + Brompheniramine maleate (4 mg/5mL) + Pseudoephedrine hydrochloride (20 mg/5mL) Liquid Oral River's Edge Pharmaceuticals, LLC 2010-01-18 2012-01-31 US Brontuss Dextromethorphan hydrobromide monohydrate (20 mg/1) + Guaifenesin (400 mg/1) Tablet Oral Portal Pharmaceuticals 2010-05-03 2012-05-31 US Carbinoxamine/Pseudoephedrine/DM Dextromethorphan hydrobromide monohydrate (4 mg/1mL) + Carbinoxamine maleate (1 mg/1mL) + Pseudoephedrine hydrochloride (15 mg/1mL) Liquid Oral Physicians Total Care, Inc. 2003-01-15 2007-08-08 US Carbofed DM Dextromethorphan hydrobromide monohydrate (15 mg/5mL) + Brompheniramine maleate (4 mg/5mL) + Pseudoephedrine hydrochloride (45 mg/5mL) Syrup Oral Hi Tech Pharmacal Co., Inc. 2001-09-03 2011-11-03 US Chlorphen Mal Dex HBr Pseudoeph HCl Dextromethorphan hydrobromide monohydrate (3 mg/1mL) + Chlorpheniramine maleate (.8 mg/1mL) + Pseudoephedrine hydrochloride (9 mg/1mL) Solution / drops Oral River's Edge Pharmaceuticals 2010-02-15 2011-01-31 US
Categories
- ATC Codes
- R05DA09 — Dextromethorphan
- R05DA — Opium alkaloids and derivatives
- R05D — COUGH SUPPRESSANTS, EXCL. COMBINATIONS WITH EXPECTORANTS
- R05 — COUGH AND COLD PREPARATIONS
- R — RESPIRATORY SYSTEM
- Drug Categories
- Alkaloids
- Anticholinergic Agents
- Antidepressive Agents
- Antitussive Agents
- Central Nervous System Agents
- Central Nervous System Depressants
- Combined Inhibitors of Serotonin/Norepinephrine Reuptake
- Cough and Cold Preparations
- Cytochrome P-450 CYP2B6 Substrates
- Cytochrome P-450 CYP2C19 Substrates
- Cytochrome P-450 CYP2C9 Substrates
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A5 Substrates
- Cytochrome P-450 CYP3A7 Substrates
- Cytochrome P-450 Substrates
- Excitatory Amino Acid Agents
- Excitatory Amino Acid Antagonists
- Heterocyclic Compounds, Fused-Ring
- Morphinans
- Narcotics
- Nervous System
- Neurotransmitter Agents
- Nicotinic Antagonists
- NMDA Receptor Antagonists
- Opiate Alkaloids
- Opioids
- Opium Alkaloids and Derivatives
- Phenanthrenes
- Respiratory System Agents
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- Serotonin Agents
- Serotonin Modulators
- Sigma-1 Agonist
- Sigma-1 Receptor Agonists
- UGT2B7 substrates
- Uncompetitive N-methyl-D-aspartate Receptor Antagonist
- Uncompetitive NMDA Receptor Antagonists
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic.
- Kingdom
- Organic compounds
- Super Class
- Alkaloids and derivatives
- Class
- Morphinans
- Sub Class
- Not Available
- Direct Parent
- Morphinans
- Alternative Parents
- Phenanthrenes and derivatives / Benzazocines / Tetralins / Anisoles / Aralkylamines / Alkyl aryl ethers / Piperidines / Trialkylamines / Azacyclic compounds / Organopnictogen compounds show 1 more
- Substituents
- Alkyl aryl ether / Amine / Anisole / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzazocine / Benzenoid / Ether / Hydrocarbon derivative show 12 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
Chemical Identifiers
- UNII
- 7355X3ROTS
- CAS number
- 125-71-3
- InChI Key
- MKXZASYAUGDDCJ-NJAFHUGGSA-N
- InChI
- InChI=1S/C18H25NO/c1-19-10-9-18-8-4-3-5-15(18)17(19)11-13-6-7-14(20-2)12-16(13)18/h6-7,12,15,17H,3-5,8-11H2,1-2H3/t15-,17+,18+/m1/s1
- IUPAC Name
- (1S,9S,10S)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,5-triene
- SMILES
- [H][C@]12CCCC[C@]11CCN(C)[C@H]2CC2=C1C=C(OC)C=C2
References
- Synthesis Reference
Mahendra R. Patel, "Sustained Release Suspension Preparation For Dextromethorphan." U.S. Patent US20130115253, issued May 09, 2013.
US20130115253- General References
- Brooks BR, Thisted RA, Appel SH, Bradley WG, Olney RK, Berg JE, Pope LE, Smith RA: Treatment of pseudobulbar affect in ALS with dextromethorphan/quinidine: a randomized trial. Neurology. 2004 Oct 26;63(8):1364-70. [PubMed:15505150]
- Olney JW, Labruyere J, Price MT: Pathological changes induced in cerebrocortical neurons by phencyclidine and related drugs. Science. 1989 Jun 16;244(4910):1360-2. [PubMed:2660263]
- Hargreaves RJ, Hill RG, Iversen LL: Neuroprotective NMDA antagonists: the controversy over their potential for adverse effects on cortical neuronal morphology. Acta Neurochir Suppl (Wien). 1994;60:15-9. [PubMed:7976530]
- Carliss RD, Radovsky A, Chengelis CP, O'Neill TP, Shuey DL: Oral administration of dextromethorphan does not produce neuronal vacuolation in the rat brain. Neurotoxicology. 2007 Jul;28(4):813-8. Epub 2007 Apr 6. [PubMed:17573115]
- Hernandez SC, Bertolino M, Xiao Y, Pringle KE, Caruso FS, Kellar KJ: Dextromethorphan and its metabolite dextrorphan block alpha3beta4 neuronal nicotinic receptors. J Pharmacol Exp Ther. 2000 Jun;293(3):962-7. [PubMed:10869398]
- Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
- Pope LE, Khalil MH, Berg JE, Stiles M, Yakatan GJ, Sellers EM: Pharmacokinetics of dextromethorphan after single or multiple dosing in combination with quinidine in extensive and poor metabolizers. J Clin Pharmacol. 2004 Oct;44(10):1132-42. doi: 10.1177/0091270004269521. [PubMed:15342614]
- Journey JD, Agrawal S, Stern E: Dextromethorphan Toxicity . [PubMed:30860737]
- Taylor CP, Traynelis SF, Siffert J, Pope LE, Matsumoto RR: Pharmacology of dextromethorphan: Relevance to dextromethorphan/quinidine (Nuedexta(R)) clinical use. Pharmacol Ther. 2016 Aug;164:170-82. doi: 10.1016/j.pharmthera.2016.04.010. Epub 2016 Apr 29. [PubMed:27139517]
- Logan BK, Goldfogel G, Hamilton R, Kuhlman J: Five deaths resulting from abuse of dextromethorphan sold over the internet. J Anal Toxicol. 2009 Mar;33(2):99-103. doi: 10.1093/jat/33.2.99. [PubMed:19239735]
- Oh SR, Agrawal S, Sabir S, Taylor A: Dextromethorphan . [PubMed:30855804]
- FDA Approved Drug Products: Nuedexta Dextromethorphan Hydrobromide and Quinidine Sulfate Oral Capsules [Link]
- Dailymed: Brompheniramine, Pseudoephedrine, and Dextromethorphan Oral Syrup [Link]
- Dailymed: Guaifenesin and Dextromethorphan Oral Extended Release Tablets [Link]
- FDA Drug Quality Assessment: Nuedexta Dextromethorphan and Quinidine Capsules [Link]
- FDA Approved Drug Products: Promethazine Hydrochloride and Dextromethorphan Hydrobromide Oral Syrup (Discontinued) [Link]
- External Links
- KEGG Drug
- D03742
- KEGG Compound
- C06947
- PubChem Compound
- 5360696
- PubChem Substance
- 46506530
- ChemSpider
- 13109865
- BindingDB
- 50366613
- 3289
- ChEBI
- 4470
- ChEMBL
- CHEMBL52440
- ZINC
- ZINC000003201907
- Therapeutic Targets Database
- DNC000541
- PharmGKB
- PA449273
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Dextromethorphan
- AHFS Codes
- 48:08.00 — Antitussives
- 48:16.00 — Expectorants
- MSDS
- Download (73.3 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Basic Science Rejection, Transplant 1 4 Completed Basic Science Type 2 Diabetes Mellitus 1 4 Completed Treatment Acute Rhinosinusitis / Respiratory Infections, Acute 1 4 Completed Treatment Atherosclerosis / Inflammatory Reaction / Smoking 1 4 Completed Treatment Dementia / Pseudobulbar Affect (PBA) / Stroke / Traumatic Brain Injury (TBI) 1 4 Completed Treatment Postoperative pain 1 4 Recruiting Other CYP2D6 Polymorphism 1 4 Recruiting Treatment Acute Tracheobronchitis 1 4 Terminated Other Pseudobulbar Affect (Involuntary Laughing and/or Crying) 1 4 Terminated Supportive Care Alzheimer's Disease (AD) / Pseudobulbar Affect (PBA) 1
Pharmacoeconomics
- Manufacturers
- Reckitt benckiser
- Packagers
- Amend
- BF Ascher & Co.
- Great Southern Laboratories
- MCR American Pharmaceuticals Inc.
- Medisca Inc.
- Novartis AG
- Pharmaceutical Association
- Prescript Pharmaceuticals
- Procter & Gamble
- Spectrum Pharmaceuticals
- The F. Dohmen Co.
- Topco
- Wyeth Pharmaceuticals
- Dosage Forms
Form Route Strength Syrup Oral 1.25 mg/5mL Syrup Oral 0.025 g/100ml Tablet Oral 2 mg Capsule Oral 15 mg/1 Liquid Oral 30 mg/10mL Solution Oral 30 mg/10mL Capsule, liquid filled Oral 4 mg Capsule, liquid filled Not applicable Tablet, effervescent Oral Granule, effervescent Oral Tablet, sugar coated Oral 1 mg Syrup Oral 0.05 g Tablet Oral 500 mg Solution Oral Suspension / drops Oral Syrup Oral 1 MG/ML Syrup Oral 2 MG/ML Tablet Transmucosal 10.5 MG Syrup Oral 150 mg/5mL Tablet 150 mg Syrup Oral 7.5 mg Syrup Oral 2.5 mg/5mL Liquid Oral Elixir Oral 5 mg/5ml Tablet, orally disintegrating Oral 7.5 MG Syrup Oral 1.54 MG/ML Tablet 7.5 MG Solution Oral 36 mg Capsule, liquid filled Oral 10 mg Syrup Oral 200 mg Syrup Oral 0.2 g Liquid Topical Lozenge Oral Solution Oral 15 mg/5mL Solution Oral Solution / drops Oral Syrup Oral 1.25 g Capsule Oral 15 MG Tablet Oral 12.5 mg Capsule; kit Oral Kit; tablet Oral Syrup Oral 120 mg/5mL Tablet Oral 2 mg/5mL Capsule, liquid filled Oral 325 mg Syrup Oral 20 mg/g Solution Oral 15 mg/15mL Tablet, sugar coated Oral Suspension Oral 30 mg/5mL Syrup Oral 15 mg Syrup Oral 20 mg/15mL Syrup Oral 5 mg/5mL Kit; powder, for solution Oral Powder Oral 500 mg Syrup Oral 133 mg Capsule Oral 1 mg/5mL Tablet, chewable Oral Syrup Oral 25 mg/10ml Suspension, extended release Oral 30 mg/5mL Syrup Oral 30 mg/5mL Suspension Oral Solution / drops Oral 1.5 % Syrup Oral 0.3 % Tablet, chewable Oral 7.65 MG Solution Oral 15 MG Syrup Oral 125 g Tablet, film coated Oral 15 MG Elixir Oral 5.5 mg/5ml Syrup Oral 0.625 mg/ml Tablet, film coated Oral 1 mg Capsule 2 mg Pastille Oral 10.5 MG Capsule, liquid filled Oral 15 mg/1 Powder Not applicable 1 g/1g Syrup Oral 0.3 g Tablet, film coated Oral Syrup Oral 3.6 mg/5ml Syrup Oral 0.1 g Tablet, chewable Oral Syrup Oral Syrup Oral 20 mg Capsule Oral 10 mg Liquid Oral 7.5 mg/5mL Capsule Oral Tablet, orally disintegrating Oral 30 mg/1 Syrup Oral 3 mg/ml Syrup Oral 1.5 mg/ml Kit Oral Liquid Oral 20 mg/5mL Tablet Oral 10 mg Syrup Oral 125 mg/5mL Tablet Oral 12 mg Syrup Oral 2 g Granule Oral Kit; powder Oral Tablet 1 mg/5mL Capsule, gelatin coated Oral 30 mg Solution / drops Oral 15 MG/ML Syrup Oral 300 MG/100ML Syrup Oral 0.5 mg/5mL Capsule 1 mg Tablet, film coated Oral 12.5 mg Tablet 75 MG Solution / drops Nasal Capsule, liquid filled Oral 30 mg Solution / drops Oral 15 MG Syrup Oral 150 mg Tablet Oral 325 mg Liquid Oral 100 mg/5ml Syrup Oral 10 mg Syrup Oral 20 mg/20mL Syrup Oral 0.06 % Tablet Transmucosal 7.5 MG Liquid Oral 3.6 mg/5ml Elixir Oral 4 mg/5ml Elixir Oral Syrup Oral 2 mg/5mL Capsule Oral 22 mg Tablet 100 mg Tablet 300 mg Strip Oral Tablet, orally disintegrating Oral Syrup Oral 100 mg/5mL Tablet 10 mg Lozenge Oral 10 mg Solution / drops Oral 15 G Tablet Oral 1 mg Tablet 1 mg Tablet, extended release Oral Tablet Oral 8 mg Capsule Oral Capsule, liquid filled Oral Capsule, gelatin coated Oral Syrup Oral 131.5 mg/5mL Solution / drops Oral 30 MG/ML Lozenge Oral 1.2 MG Strip Oral Tablet 15 mg Syrup Oral 0.15 g Capsule, coated Oral Capsule, gelatin coated Oral 15 mg/1 Capsule, liquid filled Oral 15 mg Powder, for solution Oral 500 mg Granule Oral 500 mg Capsule, liquid filled Oral 20 mg Tablet Oral 30 mg Syrup Oral 300 mg Liquid Oral Syrup Oral 62.5 mg/5mL Syrup Oral 1 mg/5mL Powder Oral 10 mg Powder Oral 12 mg Powder Oral Suspension Oral 1 mg/5mL Solution Oral 5 mg Patch Topical Syrup Oral 4 mg/5ml Tablet Oral Granule, for solution Oral Suspension Oral Tablet, chewable Oral 6.5 MG Powder, for solution Oral Solution Oral 0.2 g Liquid Oral 15 mg/5mL Syrup Oral 10 mg/5mL Capsule, liquid filled Oral 200 mg Liquid Oral 30 mg/3mL Tablet Oral 30 mg/1 Liquid Oral 10 mg/5mL Tablet, coated Oral Liquid Oral 30 mg/5mL Syrup Oral Capsule Oral 30 mg Syrup Oral 30 MG/10ML Tablet 7.65 MG Lozenge Oral 10 mg/1 Lozenge Oral Syrup Oral 100 mg/100mL Liquid Oral 15 mg/15mL Syrup Oral 1.6 g Syrup Oral 7.5 mg/5mL Tablet Oral Syrup Oral 250 mg Syrup Oral 0.02 g Syrup Oral 40 mg Syrup Oral 0.08 g Solution Oral 3 mg Solution Oral 2 mg/ml Syrup Oral 0.317 g Solution Oral 2 mg Syrup Oral 15 mg/5ml Tablet 2 mg Syrup Oral 133 MG/100ML Suspension Oral 1000 mg/1 Liquid Oral 30 mg/15mL Syrup Oral 5 mg Liquid Oral 30 mg/30mL Syrup Oral 0.05 g/100ml Syrup Oral 12.5 mg/30mL Tablet Transmucosal 7.33 MG Syrup Oral 1.33 MG/ML Syrup Oral 20 mg/5mL Pastille Oral 7.33 mg Syrup Oral 8 mg/30ml Tablet, coated Oral 250 mg Spray Oral 6 mg/0.25mL Tablet, film coated Lozenge Oral 5 mg Suspension Tablet Tablet Tablet, coated Oral Tablet, sugar coated Oral Syrup Capsule - Prices
Unit description Cost Unit Modicon (28) 28 0.5-35 mg-mcg tablet Disp Pack 59.99USD disp Dextromethorphan powder 14.93USD g Dextromethorphan hbr powder 4.74USD g Dextromethorphan hbr cryst 2.06USD g Triaminic allergy thin strip 0.35USD strip Triaminic cold-stuff nose strip 0.35USD strip Triaminic cgh-runny nose strip 0.3USD each Triaminic cough strips 0.3USD strip Triaminic cough-cold chew 0.27USD each Triaminic softchew tablet 0.27USD tablet Robitussin coughgels 0.25USD each Triaminic softchews tablet 0.25USD tablet Childrens triaminic decon spray 0.24USD ml Hold 4 hour lozenge regular 0.24USD lozenge Hca severe cough stopper cplet 0.23USD each Triaminicin tablet 0.23USD tablet Delsym 30 mg/5 ml suspension 0.11USD ml Robitussin dm to go liquid 0.09USD ml Apap allergy sinus caplet 0.05USD caplet Adlt robitussin cough-cold-flu 0.04USD ml Adt robitussin cough-cold d lq 0.04USD ml Adult robitussin cough syrup 0.04USD ml Robitussin chest congest syrup 0.04USD ml Robitussin cough & cold liquid 0.04USD ml Robitussin cough-cold liquid 0.04USD ml Robitussin cough-cong syrup 0.04USD ml Robitussin dm max liquid 0.04USD ml Robitussin long-acting liq 0.04USD ml Robitussin pe head & chest liq 0.04USD ml Robitussin-cough-chest-cong lq 0.04USD ml Robitussin-dm cough syrup 0.04USD ml Triaminic chest-nasal cong liq 0.04USD ml Triaminic cold & cough liquid 0.04USD ml Triaminic cold-allergy pe liq 0.04USD ml Triaminic cough-nasal cong liq 0.04USD ml Triaminic cough-sore throat lq 0.04USD ml Triaminic flu cough-fever susp 0.04USD ml Triaminic flu-cough-fever liq 0.04USD ml Triaminic-d syrup 0.04USD ml Vicks 44 cough liquid 0.03USD ml Vicks 44 custom care liquid 0.03USD ml Guaifenesin dm syrup 0.02USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5980882 No 1999-11-09 2017-04-16 US US6372252 No 2002-04-16 2020-04-28 US US6955821 No 2005-10-18 2020-04-28 US US7838032 No 2010-11-23 2020-04-28 US US7659282 No 2010-02-09 2026-08-13 US US8227484 No 2012-07-24 2023-07-17 US USRE38115 No 2003-05-06 2016-01-26 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 122-124 Schnider, O. and Grussner, A,; US. Patent 2,676,177; April 20, 1954; assigned to Hoffrnann-La Roche Inc. water solubility 25g/100mL FDA Drug Quality Assessment: Nudexta Dextromethorphan and Quinidine Capsules - Predicted Properties
Property Value Source Water Solubility 0.00851 mg/mL ALOGPS logP 3.75 ALOGPS logP 3.49 ChemAxon logS -4.5 ALOGPS pKa (Strongest Basic) 9.85 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 12.47 Å2 ChemAxon Rotatable Bond Count 1 ChemAxon Refractivity 82.56 m3·mol-1 ChemAxon Polarizability 31.86 Å3 ChemAxon Number of Rings 4 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
Property Value Probability Human Intestinal Absorption + 0.9959 Blood Brain Barrier + 0.9989 Caco-2 permeable + 0.8867 P-glycoprotein substrate Substrate 0.8288 P-glycoprotein inhibitor I Inhibitor 0.654 P-glycoprotein inhibitor II Non-inhibitor 0.8383 Renal organic cation transporter Inhibitor 0.7893 CYP450 2C9 substrate Non-substrate 0.8187 CYP450 2D6 substrate Substrate 0.8919 CYP450 3A4 substrate Substrate 0.7783 CYP450 1A2 substrate Non-inhibitor 0.9046 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Inhibitor 0.8932 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.8308 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8673 Ames test Non AMES toxic 0.5664 Carcinogenicity Non-carcinogens 0.9616 Biodegradation Not ready biodegradable 0.9763 Rat acute toxicity 3.3377 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7107 hERG inhibition (predictor II) Inhibitor 0.6723
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Targets
Accelerate your drug discovery research
with our fully connected ADMET & drug target dataset.
Accelerate your drug discovery research with our ADMET & drug target dataset
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Opioid receptor activity
- Specific Function
- Functions in lipid transport from the endoplasmic reticulum and is involved in a wide array of cellular functions probably through regulation of the biogenesis of lipid microdomains at the plasma m...
- Gene Name
- SIGMAR1
- Uniprot ID
- Q99720
- Uniprot Name
- Sigma non-opioid intracellular receptor 1
- Molecular Weight
- 25127.52 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
- Shin EJ, Nah SY, Chae JS, Bing G, Shin SW, Yen TP, Baek IH, Kim WK, Maurice T, Nabeshima T, Kim HC: Dextromethorphan attenuates trimethyltin-induced neurotoxicity via sigma1 receptor activation in rats. Neurochem Int. 2007 May;50(6):791-9. Epub 2007 Feb 4. [PubMed:17386960]
- Shin EJ, Nah SY, Kim WK, Ko KH, Jhoo WK, Lim YK, Cha JY, Chen CF, Kim HC: The dextromethorphan analog dimemorfan attenuates kainate-induced seizures via sigma1 receptor activation: comparison with the effects of dextromethorphan. Br J Pharmacol. 2005 Apr;144(7):908-18. [PubMed:15723099]
- Church AJ, Andrew RD: Spreading depression expands traumatic injury in neocortical brain slices. J Neurotrauma. 2005 Feb;22(2):277-90. [PubMed:15716633]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Not Available
- Specific Function
- Not Available
- Gene Name
- SIGMAR1
- Uniprot ID
- Q5T1J1
- Uniprot Name
- HCG20471, isoform CRA_c
- Molecular Weight
- 14852.655 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
- Chou YC, Liao JF, Chang WY, Lin MF, Chen CF: Binding of dimemorfan to sigma-1 receptor and its anticonvulsant and locomotor effects in mice, compared with dextromethorphan and dextrorphan. Brain Res. 1999 Mar 13;821(2):516-9. [PubMed:10064839]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Drug binding
- Specific Function
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
- Gene Name
- CHRNA2
- Uniprot ID
- Q15822
- Uniprot Name
- Neuronal acetylcholine receptor subunit alpha-2
- Molecular Weight
- 59764.82 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
- Damaj MI, Flood P, Ho KK, May EL, Martin BR: Effect of dextrometorphan and dextrorphan on nicotine and neuronal nicotinic receptors: in vitro and in vivo selectivity. J Pharmacol Exp Ther. 2005 Feb;312(2):780-5. Epub 2004 Sep 8. [PubMed:15356218]
- Lee JH, Shin EJ, Jeong SM, Kim JH, Lee BH, Yoon IS, Lee JH, Choi SH, Lee SM, Lee PH, Kim HC, Nah SY: Effects of dextrorotatory morphinans on alpha3beta4 nicotinic acetylcholine receptors expressed in Xenopus oocytes. Eur J Pharmacol. 2006 Apr 24;536(1-2):85-92. Epub 2006 Mar 2. [PubMed:16563374]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Protein phosphatase 2a binding
- Specific Function
- NMDA receptor subtype of glutamate-gated ion channels with reduced single-channel conductance, low calcium permeability and low voltage-dependent sensitivity to magnesium. Mediated by glycine. May ...
- Gene Name
- GRIN3A
- Uniprot ID
- Q8TCU5
- Uniprot Name
- Glutamate receptor ionotropic, NMDA 3A
- Molecular Weight
- 125464.07 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
- Chou YC, Liao JF, Chang WY, Lin MF, Chen CF: Binding of dimemorfan to sigma-1 receptor and its anticonvulsant and locomotor effects in mice, compared with dextromethorphan and dextrorphan. Brain Res. 1999 Mar 13;821(2):516-9. [PubMed:10064839]
- Wong BY, Coulter DA, Choi DW, Prince DA: Dextrorphan and dextromethorphan, common antitussives, are antiepileptic and antagonize N-methyl-D-aspartate in brain slices. Neurosci Lett. 1988 Feb 29;85(2):261-6. [PubMed:2897648]
- Kamel IR, Wendling WW, Chen D, Wendling KS, Harakal C, Carlsson C: N-methyl-D-aspartate (NMDA) antagonists--S(+)-ketamine, dextrorphan, and dextromethorphan--act as calcium antagonists on bovine cerebral arteries. J Neurosurg Anesthesiol. 2008 Oct;20(4):241-8. doi: 10.1097/ANA.0b013e31817f523f. [PubMed:18812887]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Serotonin:sodium symporter activity
- Specific Function
- Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into t...
- Gene Name
- SLC6A4
- Uniprot ID
- P31645
- Uniprot Name
- Sodium-dependent serotonin transporter
- Molecular Weight
- 70324.165 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
- Codd EE, Shank RP, Schupsky JJ, Raffa RB: Serotonin and norepinephrine uptake inhibiting activity of centrally acting analgesics: structural determinants and role in antinociception. J Pharmacol Exp Ther. 1995 Sep;274(3):1263-70. [PubMed:7562497]
- Henderson MG, Fuller RW: Dextromethorphan antagonizes the acute depletion of brain serotonin by p-chloroamphetamine and H75/12 in rats. Brain Res. 1992 Oct 30;594(2):323-6. [PubMed:1280529]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Steroid binding
- Specific Function
- Receptor for progesterone.
- Gene Name
- PGRMC1
- Uniprot ID
- O00264
- Uniprot Name
- Membrane-associated progesterone receptor component 1
- Molecular Weight
- 21670.9 Da
References
- Chou YC, Liao JF, Chang WY, Lin MF, Chen CF: Binding of dimemorfan to sigma-1 receptor and its anticonvulsant and locomotor effects in mice, compared with dextromethorphan and dextrorphan. Brain Res. 1999 Mar 13;821(2):516-9. [PubMed:10064839]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Ligand-gated ion channel activity
- Specific Function
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
- Gene Name
- CHRNA3
- Uniprot ID
- P32297
- Uniprot Name
- Neuronal acetylcholine receptor subunit alpha-3
- Molecular Weight
- 57479.54 Da
References
- Damaj MI, Flood P, Ho KK, May EL, Martin BR: Effect of dextrometorphan and dextrorphan on nicotine and neuronal nicotinic receptors: in vitro and in vivo selectivity. J Pharmacol Exp Ther. 2005 Feb;312(2):780-5. Epub 2004 Sep 8. [PubMed:15356218]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Ligand-gated ion channel activity
- Specific Function
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane permeabl...
- Gene Name
- CHRNA4
- Uniprot ID
- P43681
- Uniprot Name
- Neuronal acetylcholine receptor subunit alpha-4
- Molecular Weight
- 69956.47 Da
References
- Damaj MI, Flood P, Ho KK, May EL, Martin BR: Effect of dextrometorphan and dextrorphan on nicotine and neuronal nicotinic receptors: in vitro and in vivo selectivity. J Pharmacol Exp Ther. 2005 Feb;312(2):780-5. Epub 2004 Sep 8. [PubMed:15356218]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Ligand-gated ion channel activity
- Specific Function
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
- Gene Name
- CHRNB4
- Uniprot ID
- P30926
- Uniprot Name
- Neuronal acetylcholine receptor subunit beta-4
- Molecular Weight
- 56378.985 Da
References
- Damaj MI, Flood P, Ho KK, May EL, Martin BR: Effect of dextrometorphan and dextrorphan on nicotine and neuronal nicotinic receptors: in vitro and in vivo selectivity. J Pharmacol Exp Ther. 2005 Feb;312(2):780-5. Epub 2004 Sep 8. [PubMed:15356218]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Ligand-gated ion channel activity
- Specific Function
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane permeabl...
- Gene Name
- CHRNB2
- Uniprot ID
- P17787
- Uniprot Name
- Neuronal acetylcholine receptor subunit beta-2
- Molecular Weight
- 57018.575 Da
References
- Damaj MI, Flood P, Ho KK, May EL, Martin BR: Effect of dextrometorphan and dextrorphan on nicotine and neuronal nicotinic receptors: in vitro and in vivo selectivity. J Pharmacol Exp Ther. 2005 Feb;312(2):780-5. Epub 2004 Sep 8. [PubMed:15356218]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Toxic substance binding
- Specific Function
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane. The cha...
- Gene Name
- CHRNA7
- Uniprot ID
- P36544
- Uniprot Name
- Neuronal acetylcholine receptor subunit alpha-7
- Molecular Weight
- 56448.925 Da
References
- Damaj MI, Flood P, Ho KK, May EL, Martin BR: Effect of dextrometorphan and dextrorphan on nicotine and neuronal nicotinic receptors: in vitro and in vivo selectivity. J Pharmacol Exp Ther. 2005 Feb;312(2):780-5. Epub 2004 Sep 8. [PubMed:15356218]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Voltage-gated calcium channel activity
- Specific Function
- Receptor for endogenous opioids such as beta-endorphin and endomorphin. Receptor for natural and synthetic opioids including morphine, heroin, DAMGO, fentanyl, etorphine, buprenorphin and methadone...
- Gene Name
- OPRM1
- Uniprot ID
- P35372
- Uniprot Name
- Mu-type opioid receptor
- Molecular Weight
- 44778.855 Da
References
- Codd EE, Shank RP, Schupsky JJ, Raffa RB: Serotonin and norepinephrine uptake inhibiting activity of centrally acting analgesics: structural determinants and role in antinociception. J Pharmacol Exp Ther. 1995 Sep;274(3):1263-70. [PubMed:7562497]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Opioid receptor activity
- Specific Function
- G-protein coupled receptor that functions as receptor for endogenous enkephalins and for a subset of other opioids. Ligand binding causes a conformation change that triggers signaling via guanine n...
- Gene Name
- OPRD1
- Uniprot ID
- P41143
- Uniprot Name
- Delta-type opioid receptor
- Molecular Weight
- 40368.235 Da
References
- Codd EE, Shank RP, Schupsky JJ, Raffa RB: Serotonin and norepinephrine uptake inhibiting activity of centrally acting analgesics: structural determinants and role in antinociception. J Pharmacol Exp Ther. 1995 Sep;274(3):1263-70. [PubMed:7562497]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Opioid receptor activity
- Specific Function
- G-protein coupled opioid receptor that functions as receptor for endogenous alpha-neoendorphins and dynorphins, but has low affinity for beta-endorphins. Also functions as receptor for various synt...
- Gene Name
- OPRK1
- Uniprot ID
- P41145
- Uniprot Name
- Kappa-type opioid receptor
- Molecular Weight
- 42644.665 Da
References
- Codd EE, Shank RP, Schupsky JJ, Raffa RB: Serotonin and norepinephrine uptake inhibiting activity of centrally acting analgesics: structural determinants and role in antinociception. J Pharmacol Exp Ther. 1995 Sep;274(3):1263-70. [PubMed:7562497]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Voltage-gated ion channel activity
- Specific Function
- Critical component of the membrane-bound oxidase of phagocytes that generates superoxide. It is the terminal component of a respiratory chain that transfers single electrons from cytoplasmic NADPH ...
Components:
References
- Zhang W, Wang T, Qin L, Gao HM, Wilson B, Ali SF, Zhang W, Hong JS, Liu B: Neuroprotective effect of dextromethorphan in the MPTP Parkinson's disease model: role of NADPH oxidase. FASEB J. 2004 Mar;18(3):589-91. Epub 2004 Jan 20. [PubMed:14734632]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Norepinephrine:sodium symporter activity
- Specific Function
- Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
- Gene Name
- SLC6A2
- Uniprot ID
- P23975
- Uniprot Name
- Sodium-dependent noradrenaline transporter
- Molecular Weight
- 69331.42 Da
References
- Codd EE, Shank RP, Schupsky JJ, Raffa RB: Serotonin and norepinephrine uptake inhibiting activity of centrally acting analgesics: structural determinants and role in antinociception. J Pharmacol Exp Ther. 1995 Sep;274(3):1263-70. [PubMed:7562497]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Zhou SF: Polymorphism of human cytochrome P450 2D6 and its clinical significance: Part I. Clin Pharmacokinet. 2009;48(11):689-723. doi: 10.2165/11318030-000000000-00000. [PubMed:19817501]
- Zhang T, Zhu Y, Gunaratna C: Rapid and quantitative determination of metabolites from multiple cytochrome P450 probe substrates by gradient liquid chromatography-electrospray ionization-ion trap mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Nov 25;780(2):371-9. [PubMed:12401364]
- Yu A, Haining RL: Comparative contribution to dextromethorphan metabolism by cytochrome P450 isoforms in vitro: can dextromethorphan be used as a dual probe for both CTP2D6 and CYP3A activities? Drug Metab Dispos. 2001 Nov;29(11):1514-20. [PubMed:11602530]
- Zawertailo LA, Kaplan HL, Busto UE, Tyndale RF, Sellers EM: Psychotropic effects of dextromethorphan are altered by the CYP2D6 polymorphism: a pilot study. J Clin Psychopharmacol. 1998 Aug;18(4):332-7. [PubMed:9690700]
- Yuan R, Madani S, Wei XX, Reynolds K, Huang SM: Evaluation of cytochrome P450 probe substrates commonly used by the pharmaceutical industry to study in vitro drug interactions. Drug Metab Dispos. 2002 Dec;30(12):1311-9. [PubMed:12433797]
- Flockhart Table of Drug Interactions [Link]
- Source [Link]
- FDA Approved Drug Products: Nuedexta Dextromethorphan Hydrobromide and Quinidine Sulfate Oral Capsules [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Yu A, Haining RL: Comparative contribution to dextromethorphan metabolism by cytochrome P450 isoforms in vitro: can dextromethorphan be used as a dual probe for both CTP2D6 and CYP3A activities? Drug Metab Dispos. 2001 Nov;29(11):1514-20. [PubMed:11602530]
- Wang Y, Unadkat JD: Enzymes in addition to CYP3A4 and 3A5 mediate N-demethylation of dextromethorphan in human liver microsomes. Biopharm Drug Dispos. 1999 Oct;20(7):341-6. [PubMed:10760842]
- Schmider J, Greenblatt DJ, Fogelman SM, von Moltke LL, Shader RI: Metabolism of dextromethorphan in vitro: involvement of cytochromes P450 2D6 and 3A3/4, with a possible role of 2E1. Biopharm Drug Dispos. 1997 Apr;18(3):227-40. doi: 10.1002/(sici)1099-081x(199704)18:3<227::aid-bdd18>3.0.co;2-l. [PubMed:9113345]
- Flockhart Table of Drug Interactions [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Oxygen binding
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP3A7
- Uniprot ID
- P24462
- Uniprot Name
- Cytochrome P450 3A7
- Molecular Weight
- 57525.03 Da
References
- Gorski JC, Jones DR, Wrighton SA, Hall SD: Characterization of dextromethorphan N-demethylation by human liver microsomes. Contribution of the cytochrome P450 3A (CYP3A) subfamily. Biochem Pharmacol. 1994 Jul 5;48(1):173-82. doi: 10.1016/0006-2952(94)90237-2. [PubMed:8043020]
- Flockhart Table of Drug Interactions [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2B6
- Uniprot ID
- P20813
- Uniprot Name
- Cytochrome P450 2B6
- Molecular Weight
- 56277.81 Da
References
- Yu A, Haining RL: Comparative contribution to dextromethorphan metabolism by cytochrome P450 isoforms in vitro: can dextromethorphan be used as a dual probe for both CTP2D6 and CYP3A activities? Drug Metab Dispos. 2001 Nov;29(11):1514-20. [PubMed:11602530]
- Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
- Gene Name
- CYP2C19
- Uniprot ID
- P33261
- Uniprot Name
- Cytochrome P450 2C19
- Molecular Weight
- 55930.545 Da
References
- von Moltke LL, Greenblatt DJ, Grassi JM, Granda BW, Venkatakrishnan K, Schmider J, Harmatz JS, Shader RI: Multiple human cytochromes contribute to biotransformation of dextromethorphan in-vitro: role of CYP2C9, CYP2C19, CYP2D6, and CYP3A. J Pharm Pharmacol. 1998 Sep;50(9):997-1004. doi: 10.1111/j.2042-7158.1998.tb06914.x. [PubMed:9811160]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
- Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
- Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]
- von Moltke LL, Greenblatt DJ, Grassi JM, Granda BW, Venkatakrishnan K, Schmider J, Harmatz JS, Shader RI: Multiple human cytochromes contribute to biotransformation of dextromethorphan in-vitro: role of CYP2C9, CYP2C19, CYP2D6, and CYP3A. J Pharm Pharmacol. 1998 Sep;50(9):997-1004. doi: 10.1111/j.2042-7158.1998.tb06914.x. [PubMed:9811160]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Glucuronosyltransferase activity
- Specific Function
- UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as...
- Gene Name
- UGT2B4
- Uniprot ID
- P06133
- Uniprot Name
- UDP-glucuronosyltransferase 2B4
- Molecular Weight
- 60512.035 Da
References
- Lutz JD, Isoherranen N: Prediction of relative in vivo metabolite exposure from in vitro data using two model drugs: dextromethorphan and omeprazole. Drug Metab Dispos. 2012 Jan;40(1):159-68. doi: 10.1124/dmd.111.042200. Epub 2011 Oct 18. [PubMed:22010218]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Glucuronosyltransferase activity
- Specific Function
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.Its unique specificity for 3,4-catechol estrogens and estriol su...
- Gene Name
- UGT2B7
- Uniprot ID
- P16662
- Uniprot Name
- UDP-glucuronosyltransferase 2B7
- Molecular Weight
- 60694.12 Da
References
- Lutz JD, Isoherranen N: Prediction of relative in vivo metabolite exposure from in vitro data using two model drugs: dextromethorphan and omeprazole. Drug Metab Dispos. 2012 Jan;40(1):159-68. doi: 10.1124/dmd.111.042200. Epub 2011 Oct 18. [PubMed:22010218]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Glucuronosyltransferase activity
- Specific Function
- UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme displays activity toward several classes of xeno...
- Gene Name
- UGT2B15
- Uniprot ID
- P54855
- Uniprot Name
- UDP-glucuronosyltransferase 2B15
- Molecular Weight
- 61035.815 Da
References
- Lutz JD, Isoherranen N: Prediction of relative in vivo metabolite exposure from in vitro data using two model drugs: dextromethorphan and omeprazole. Drug Metab Dispos. 2012 Jan;40(1):159-68. doi: 10.1124/dmd.111.042200. Epub 2011 Oct 18. [PubMed:22010218]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Glucuronosyltransferase activity
- Specific Function
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. The major substrates of this isozyme are eugenol > 4-methylumbe...
- Gene Name
- UGT2B17
- Uniprot ID
- O75795
- Uniprot Name
- UDP-glucuronosyltransferase 2B17
- Molecular Weight
- 61094.915 Da
References
- Lutz JD, Isoherranen N: Prediction of relative in vivo metabolite exposure from in vitro data using two model drugs: dextromethorphan and omeprazole. Drug Metab Dispos. 2012 Jan;40(1):159-68. doi: 10.1124/dmd.111.042200. Epub 2011 Oct 18. [PubMed:22010218]
Drug created on June 13, 2005 13:24 / Updated on February 24, 2021 19:34