Dextromethorphan

Identification

Summary

Dextromethorphan is an NMDA receptor antagonist used to treat cases of dry cough.

Brand Names
Auvelity, Benylin DM, Bromfed DM, Broncotron, Cepacol Sore Throat Plus Cough, Cheracol D, Children's Nyquil Cold and Cough, Chloraseptic Sore Throat + Cough, Coricidin Hbp Chest Congestion, Coricidin Hbp Cough and Cold, Creomulsion, DM, Dayquil Cough, Delsym, Delsym Cough Plus Chest Congestion DM, Delsym Cough Plus Soothing Action, Delsym Cough Relief Plus Soothing Action, Despec Reformulated Jun 2008, Diabetic Tussin DM, Dimetapp Long Acting Cough Plus Cold, Diphen, G-zyncof, Mucinex Children's Cough, Mucinex Cough, Mucinex DM, Nuedexta, Nyquil Cough, Pediacare Children's Cough and Congestion, Promethazine DM, Robafen Cough, Robafen DM, Robitussin 12 Hour Cough Relief, Robitussin Cough & Congestion, Robitussin Maximum Strength Cough Plus Chest Congestion DM, Robitussin Nighttime Cough DM, Robitussin Pediatric Cough & Cold LA, Robitussin Pediatric Cough Suppressant, Safetussin DM, Safetussin PM, Scot-tussin DM, Scot-tussin Diabetic CF, Scot-tussin Sugar Free DM, Sudafed PE Children's Cold & Cough, Triaminic Day Time Cold & Cough, Tusnel Diabetic
Generic Name
Dextromethorphan
DrugBank Accession Number
DB00514
Background

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 1957.11,17

Type
Small Molecule
Groups
Approved
Structure
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

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.14 Dextromethorphan is also used in combination with guaifenesin as an over-the-counter product to relieve a cough.15 Dextromethorphan in combination with quinidine is indicated in the treatment of pseudobulbar affect.13

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to treatAllergic coughCombination Product in combination with: Terpin hydrate (DB13163), Chlorpheniramine (DB01114)••••••••••••••••••• ••••••• ••••••
Used in combination for symptomatic treatment ofCommon coldCombination Product in combination with: Phenylephrine (DB00388), Chlorpheniramine (DB01114), Ibuprofen (DB01050)••• ••••••••••• •••••• ••••••
Used in combination for symptomatic treatment ofCommon coldCombination Product in combination with: Acetaminophen (DB00316), Chlorpheniramine (DB01114)••• •••
Used in combination for symptomatic treatment ofCommon coldCombination Product in combination with: Pseudoephedrine (DB00852), Diphenhydramine (DB01075), Guaifenesin (DB00874)•••••••••••••••••••• •••••••• • •••••• •••••
Used in combination for symptomatic treatment ofCommon coldCombination Product in combination with: Pseudoephedrine (DB00852), Acetaminophen (DB00316)•••••••••••••••••••• •••••• ••••••
Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

Dextromethorphan is an opioid-like molecule indicated in combination with other medication in the treatment of coughs and pseudobulbar affect.14,15,13 It has a moderate therapeutic window, as intoxication can occur at higher doses.10 Dextromethorphan has a moderate duration of action.13 Patients should be counselled regarding the risk of intoxication.10

Mechanism of action

Dextromethorphan is an agonist of NMDA and sigma-1 receptors.13 It is also an antagonist of α3/β4 nicotinic receptors.12 However, the mechanism by which dextromethorphan's receptor agonism and antagonism translates to a clinical effect is not well understood.9

TargetActionsOrganism
ASigma non-opioid intracellular receptor 1
agonist
Humans
AGlutamate receptor ionotropic, NMDA 3A
antagonist
Humans
UNeuronal acetylcholine receptor subunit alpha-2
antagonist
Humans
USodium-dependent serotonin transporter
inhibitor
Humans
UMembrane-associated progesterone receptor component 1
binder
Humans
UNeuronal acetylcholine receptor subunit alpha-3
antagonist
Humans
UNeuronal acetylcholine receptor subunit alpha-4
antagonist
Humans
UNeuronal acetylcholine receptor subunit beta-4
antagonist
Humans
UNeuronal acetylcholine receptor subunit beta-2
antagonist
Humans
UNeuronal acetylcholine receptor subunit alpha-7
antagonist
Humans
UMu-type opioid receptor
agonist
regulator
Humans
UDelta-type opioid receptor
agonist
Humans
UKappa-type opioid receptor
agonist
Humans
UNADPH oxidase
inhibitor
Humans
USodium-dependent noradrenaline transporter
inhibitor
Humans
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.13

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

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Route of elimination

Not Available

Half-life

Dextromethorphan has a half life of 3-30 hours.8

Clearance

Not Available

Adverse Effects
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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.13 Overdose should be managed through symptomatic and supportive measures.13

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Cytochrome P450 2D6CYP2D6*4(A;A)A Allele, homozygoteEffect Directly StudiedPatients with this genotype have reduced metabolism of dextromethorphan.Details
Cytochrome P450 2D6CYP2D6*6(-;-)T deletion, homozygoteEffect Directly StudiedPatients with this genotype have reduced metabolism of dextromethorphan.Details
Cytochrome P450 2D6CYP2D6*3Not AvailableC alleleEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2D6CYP2D6*5Not AvailableWhole-gene deletionEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2D6CYP2D6*7Not Available2935A>CEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2D6CYP2D6*8Not Available1758G>TEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2D6CYP2D6*11Not Available883G>CEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2D6CYP2D6*12Not Available124G>AEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2D6CYP2D6*13Not AvailableCYP2D7/2D6 hybrid gene structureEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2D6CYP2D6*14ANot Available1758G>AEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2D6CYP2D6*15Not Available137insT, 137_138insTEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2D6CYP2D6*19Not Available2539_2542delAACTEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2D6CYP2D6*20Not Available1973_1974insGEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2D6CYP2D6*21Not Available2573insCEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2D6CYP2D6*31Not Available-1770G>A / -1584C>G  … show all Effect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2D6CYP2D6*36Not Available100C>T / -1426C>T  … show all Effect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2D6CYP2D6*38Not Available2587_2590delGACTEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2D6CYP2D6*40Not Available1863_1864ins(TTT CGC CCC)2Effect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2D6CYP2D6*42Not Available3259_3260insGTEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2D6CYP2D6*44Not Available2950G>CEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2D6CYP2D6*47Not Available100C>T / -1426C>T  … show all Effect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2D6CYP2D6*51Not Available-1584C>G / -1235A>G  … show all Effect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2D6CYP2D6*56Not Available3201C>TEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2D6CYP2D6*57Not Available100C>T / 310G>T  … show all Effect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2D6CYP2D6*62Not Available4044C>TEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2D6CYP2D6*68ANot Available-1426C>T / -1235A>G  … show all Effect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2D6CYP2D6*68BNot AvailableSimilar but not identical switch region compared to CYP2D6*68A. Found in tandem arrangement with CYP2D6*4.Effect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2D6CYP2D6*69Not Available2988G>A / -1426C>T  … show all Effect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2D6CYP2D6*92Not Available1995delCEffect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2D6CYP2D6*100Not Available-1426C>T / -1235A>G  … show all Effect InferredPoor drug metabolizer, lower dose requirementsDetails
Cytochrome P450 2D6CYP2D6*101Not Available-1426C>T / -1235A>G  … show all Effect InferredPoor drug metabolizer, lower dose requirementsDetails

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 CNS depression can be increased when Dextromethorphan is combined with 1,2-Benzodiazepine.
AbametapirThe serum concentration of Dextromethorphan can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Dextromethorphan can be increased when combined with Abatacept.
AbirateroneThe metabolism of Dextromethorphan can be decreased when combined with Abiraterone.
AbrocitinibThe metabolism of Abrocitinib can be decreased when combined with Dextromethorphan.
Food Interactions
  • Take with or without food. The absorption is unaffected by food.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Dextromethorphan hydriodide086F8ZEM777487-74-3RWSHVMCJJPXQSP-URVXVIKDSA-N
Dextromethorphan hydrobromideZ0CG3115FG125-69-9MISZALMBODQYFT-URVXVIKDSA-N
Dextromethorphan hydrobromide monohydrate9D2RTI9KYH6700-34-1STTADZBLEUMJRG-IKNOHUQMSA-N
Dextromethorphan hydrochloride351KFH969D18609-21-7SNDDIRAXSDUVKW-URVXVIKDSA-N
Active Moieties
NameKindUNIICASInChI Key
Dextrorphanprodrug04B7QNO9WS125-73-5JAQUASYNZVUNQP-PVAVHDDUSA-N
Product Images
International/Other Brands
Benylin DM (McNeil) / Romilar (Bayer) / Triaminic (Novartis) / Vicks Formula 44 (Procter & Gamble)
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
12 Hour Cough ReliefSuspension30 mg/5mLOralWestern Family Foods2013-07-032017-04-01US flag
12 Hour Cough ReliefSuspension30 mg/5mLOralWestern Family Foods2012-09-142017-05-01US flag
7 Select Cough DMSuspension30 mg/5mLOral7 Eleven2014-09-052016-10-01US flag
Adult Cough Relief DMLiquid30 mg/10mLOralSafeway, Inc.2014-06-302025-06-30US flag
Adult Honey WorksSyrup5 mg / 5 mLOralLifelab Health Llc2018-10-09Not applicableCanada flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
24/7 Life Cold and Flu DayTime SevereDextromethorphan hydrobromide monohydrate (10 mg/1) + Acetaminophen (325 mg/1) + Guaifenesin (200 mg/1) + Phenylephrine hydrochloride (5 mg/1)Tablet, film coatedOralLil' Drug Store Products, Inc.2021-10-27Not applicableUS flag
7 Select Day Time ReliefDextromethorphan hydrobromide monohydrate (10 mg/15mL) + Acetaminophen (325 mg/15mL) + Phenylephrine hydrochloride (5 mg/15mL)SolutionOral7-Eleven2014-08-052020-10-31US flag
7 Select Day Time ReliefDextromethorphan hydrobromide monohydrate (10 mg/1) + Acetaminophen (325 mg/1) + Phenylephrine hydrochloride (5 mg/1)Capsule, liquid filledOral7-Eleven2014-04-222020-01-31US flag
7 Select Maximum StrengthDextromethorphan hydrobromide monohydrate (20 mg/20mL) + Guaifenesin (400 mg/20mL)SolutionOral7-Eleven2019-03-25Not applicableUS flag
7 Select Night Time ReliefDextromethorphan hydrobromide monohydrate (15 mg/1) + Acetaminophen (325 mg/1) + Doxylamine succinate (6.25 mg/1)Capsule, liquid filledOral7-Eleven2014-04-172020-07-31US flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Alahist DMDextromethorphan hydrobromide monohydrate (10 mg/5mL) + Pheniramine maleate (12.5 mg/5mL) + Phenylephrine hydrochloride (5 mg/5mL)LiquidOralPoly Pharmaceuticals, Inc.2023-06-08Not applicableUS flag
AquanazDextromethorphan hydrobromide monohydrate (15 mg/1) + Guaifenesin (400 mg/1) + Phenylephrine hydrochloride (10 mg/1)TabletOralCapital Pharmaceutical, LLC2015-03-10Not applicableUS flag
Atuss DS Tannate SuspensionDextromethorphan hydrobromide monohydrate (30 mg/5mL) + Chlorpheniramine maleate (4 mg/5mL) + Pseudoephedrine hydrochloride (30 mg/5mL)SuspensionOralAtley Pharmaceuticals2006-11-21Not applicableUS flag
BPM Mal Phenyleph HCl DM HBrDextromethorphan hydrobromide monohydrate (20 mg/5mL) + Brompheniramine maleate (4 mg/5mL) + Phenylephrine hydrochloride (10 mg/5mL)LiquidOralRiver's Edge Pharmaceuticals, LLC2010-01-182012-01-31US flag
Brom Mal Phenyl HCl Dex HBrDextromethorphan hydrobromide monohydrate (15 mg/5mL) + Brompheniramine maleate (4 mg/5mL) + Phenylephrine hydrochloride (7.5 mg/5mL)LiquidOralRiver's Edge Pharmaceuticals, LLC2010-02-102012-02-29US flag

Categories

ATC Codes
R05DA09 — DextromethorphanN07XX59 — Dextromethorphan, combinations
Drug Categories
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
Affected organisms
  • Humans and other mammals

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
  1. 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. [Article]
  2. 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. [Article]
  3. 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. [Article]
  4. 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. [Article]
  5. 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. [Article]
  6. 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. [Article]
  7. 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. [Article]
  8. Journey JD, Agrawal S, Stern E: Dextromethorphan Toxicity . [Article]
  9. 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. [Article]
  10. 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. [Article]
  11. Oh SR, Agrawal S, Sabir S, Taylor A: Dextromethorphan . [Article]
  12. 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. [Article]
  13. FDA Approved Drug Products: Nuedexta Dextromethorphan Hydrobromide and Quinidine Sulfate Oral Capsules [Link]
  14. Dailymed: Brompheniramine, Pseudoephedrine, and Dextromethorphan Oral Syrup [Link]
  15. Dailymed: Guaifenesin and Dextromethorphan Oral Extended Release Tablets [Link]
  16. FDA Drug Quality Assessment: Nuedexta Dextromethorphan and Quinidine Capsules [Link]
  17. FDA Approved Drug Products: Promethazine Hydrochloride and Dextromethorphan Hydrobromide Oral Syrup (Discontinued) [Link]
  18. FDA Approved Drug Products: AUVELITY (dextromethorphan hydrobromide and bupropion hydrochloride) extended-release tablets, for oral use [Link]
KEGG Drug
D03742
KEGG Compound
C06947
PubChem Compound
5360696
PubChem Substance
46506530
ChemSpider
13109865
BindingDB
50366613
RxNav
3289
ChEBI
4470
ChEMBL
CHEMBL52440
ZINC
ZINC000003201907
Therapeutic Targets Database
DNC000541
PharmGKB
PA449273
Drugs.com
Drugs.com Drug Page
Wikipedia
Dextromethorphan
MSDS
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Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedBasic ScienceTransplanted Organ Rejection1
4CompletedBasic ScienceType 2 Diabetes Mellitus1
4CompletedOtherCYP2D6 Polymorphism1
4CompletedTreatmentAcute Respiratory Infections (ARIs) / Acute rhino-sinusitis1
4CompletedTreatmentAcute Tracheobronchitis1

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
FormRouteStrength
CapsuleOral15 mg/1
LiquidOral30 mg/10mL
SolutionOral30 mg/10mL
Capsule, liquid filledNot applicable
Tablet, effervescentOral
Granule, effervescentOral
Tablet, multilayer, extended releaseOral
ElixirOral15.75 mg/5ml
SyrupOral0.200 g
SyrupOral30 mg / 5 mL
LozengeOral30 mg
LiquidOral7.5 mg / unit
LozengeOral7.5 mg / loz
LozengeOral7.5 mg
StripOral15 mg
SyrupOral30 mg / 10 mL
SolutionOral7.5 mg / 5 mL
Suspension / dropsOral
SyrupOral2 MG/ML
TabletTransmucosal10.5 MG
LiquidOral
SyrupOral0.15 g
LiquidOral12.5 mg / 5 mL
SolutionOral15 mg / 5 mL
LiquidTopical
CapsuleOral250.0000 mg
LozengeOral
SolutionOral15 mg/5mL
SolutionOral
Solution / dropsOral
CapsuleOral15 MG
Kit; tablet, coatedOral
Capsule, gelatin coatedOral10.50 mg
Capsule, gelatin coated; kit; tabletOral
SolutionOral15 mg/15mL
Tablet, sugar coatedOral
SuspensionOral30 mg/5mL
LiquidOral30 mg / 5 mL
SyrupOral20 mg/15mL
SyrupOral5 mg/5mL
Kit; liquid; solutionOral
Kit; tablet; tablet, coatedOral
Kit; liquidOral
Capsule; kitOral
Capsule, gelatin coated; capsule, liquid filled; kitOral
SyrupOral0.300 g
Tablet, chewableOral
Suspension, extended releaseOral30 mg/5mL
SyrupOral30 mg/5mL
Kit; suspension, extended releaseOral
TabletOral15 mg/1
SuspensionOral30 mg / 5 mL
Tablet, chewableOral
CapsuleOral
SolutionOral
Tablet, film coatedOral
ElixirOral5.5 mg/5ml
Tablet, film coatedOral15 mg
Capsule
PastilleOral10.5 MG
Capsule, liquid filledOral15 mg/1
PowderNot applicable1 g/1g
ElixirOral15 mg/5ml
SyrupOral0.3 g
Tablet, film coatedOral
SyrupNot applicable
Elixir; kit; solutionOral
Cream; kit; liquid; ointment; tablet; tablet, chewable; tablet, film coatedOral; Topical
Tablet, chewableOral7.5 mg / tab
SyrupOral7.5 mg / 5 mL
SyrupOral15 mg / 5 mL
CapsuleOral10 mg
LiquidOral7.5 mg/5mL
TabletOral15 mg
CapsuleOral30 mg
Tablet, orally disintegratingOral30 mg/1
SyrupOral3 mg/ml
SyrupOral1.5 mg/ml
KitOral
LiquidOral20 mg/5mL
TabletOral10 mg
GranuleOral650.00 mg
GranuleOral
Kit; powderOral
Solution / dropsOral
SyrupOral
Solution / dropsNasal
Capsule, liquid filledOral30 mg
SyrupOral30 mg/1
SyrupOral20 mg/20mL
TabletTransmucosal
ElixirOral
StripOral7.5 mg
Tablet7.5 MG
Tablet, orally disintegratingOral
Tablet
Solution / dropsOral15 G
Kit; tabletOral
SuppositoryRectal
SyrupOral2 mg/5ml
Kit; solution; suspensionOral
Tablet, extended releaseOral
Kit; tablet, film coatedOral
Kit; tablet, coated; tablet, film coatedOral
Capsule, liquid filled; kit; solutionNasal; Oral
SyrupOral5 mg/5ml
TabletOral8 mg
CapsuleOral
Capsule, liquid filledOral
Capsule, gelatin coatedOral
Solution / dropsOral30 MG/ML
SyrupOral30 MG/10ML
SyrupOral300.000 mg
StripOral
Capsule, coatedOral
Capsule, gelatin coatedOral15 mg/1
TabletOral30.00 mg
TabletOral
SyrupOral300 mg
LiquidOral15 mg / 5 mL
LiquidOral7.5 mg / 5 mL
PowderOral10 mg
SyrupOral1 mg/5ml
TabletOral15 mg
PowderOral
SyrupOral0.2 g
PatchTopical
TabletOral
Granule, for solutionOral
SolutionOral0.1000 g
TabletOral15.000 mg
SuspensionOral
SyrupOral0.1330 g
Capsule, liquid filled; kitOral
Powder, for solutionOral
LiquidOral15 mg/5mL
SyrupOral10 mg / 5 mL
SyrupOral10 mg/5mL
LiquidOral30 mg/3mL
TabletOral30 mg/1
LiquidOral10 mg/5mL
Tablet, coatedOral
LiquidOral30 mg/5mL
SyrupOral
Tablet
LozengeOral10 mg/1
LozengeOral15 mg
LozengeOral10 mg
SyrupOral125 mg/5ml
LiquidOral15 mg/15mL
Kit; solutionOral
Kit; powder, for solutionOral
Kit; powder; syrupOral
SyrupOral7.5 mg/5mL
TabletOral7.5 mg
SyrupOral1.500 g
Kit; syrupOral
SolutionOral2 mg/ml
TabletOral500.000 mg
SyrupOral133 MG/100ML
SuspensionOral1000 mg/1
Kit; suspensionOral
LiquidOral30 mg/15mL
LiquidOral30 mg / 15 mL
SyrupOral5 mg / 5 mL
LiquidOral30 mg/30mL
LiquidOral15 mg / 15 mL
SyrupOral1.33 MG/ML
PastilleOral
CapsuleOral10.00 mg
CapsuleOral250.000 mg
SprayOral6 mg/0.25mL
Tablet, film coated
LozengeOral5 mg
Suspension
SyrupOral15 mg/5ml
Tablet15 mg
Tablet, coatedOral30 mg
Tablet, coatedOral15 mg
Tablet, sugar coatedOral15 mg
Syrup
Prices
Unit descriptionCostUnit
Modicon (28) 28 0.5-35 mg-mcg tablet Disp Pack59.99USD disp
Dextromethorphan powder14.93USD g
Dextromethorphan hbr powder4.74USD g
Dextromethorphan hbr cryst2.06USD g
Triaminic allergy thin strip0.35USD strip
Triaminic cold-stuff nose strip0.35USD strip
Triaminic cgh-runny nose strip0.3USD each
Triaminic cough strips0.3USD strip
Triaminic cough-cold chew0.27USD each
Triaminic softchew tablet0.27USD tablet
Robitussin coughgels0.25USD each
Triaminic softchews tablet0.25USD tablet
Childrens triaminic decon spray0.24USD ml
Hold 4 hour lozenge regular0.24USD lozenge
Hca severe cough stopper cplet0.23USD each
Triaminicin tablet0.23USD tablet
Delsym 30 mg/5 ml suspension0.11USD ml
Robitussin dm to go liquid0.09USD ml
Apap allergy sinus caplet0.05USD caplet
Adlt robitussin cough-cold-flu0.04USD ml
Adt robitussin cough-cold d lq0.04USD ml
Adult robitussin cough syrup0.04USD ml
Robitussin chest congest syrup0.04USD ml
Robitussin cough & cold liquid0.04USD ml
Robitussin cough-cold liquid0.04USD ml
Robitussin cough-cong syrup0.04USD ml
Robitussin dm max liquid0.04USD ml
Robitussin long-acting liq0.04USD ml
Robitussin pe head & chest liq0.04USD ml
Robitussin-cough-chest-cong lq0.04USD ml
Robitussin-dm cough syrup0.04USD ml
Triaminic chest-nasal cong liq0.04USD ml
Triaminic cold & cough liquid0.04USD ml
Triaminic cold-allergy pe liq0.04USD ml
Triaminic cough-nasal cong liq0.04USD ml
Triaminic cough-sore throat lq0.04USD ml
Triaminic flu cough-fever susp0.04USD ml
Triaminic flu-cough-fever liq0.04USD ml
Triaminic-d syrup0.04USD ml
Vicks 44 cough liquid0.03USD ml
Vicks 44 custom care liquid0.03USD ml
Guaifenesin dm syrup0.02USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5980882No1999-11-092017-04-16US flag
US6372252No2002-04-162020-04-28US flag
US6955821No2005-10-182020-04-28US flag
US7838032No2010-11-232020-04-28US flag
US7659282No2010-02-092026-08-13US flag
US8227484No2012-07-242023-07-17US flag
USRE38115No2003-05-062016-01-26US flag
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Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)122-124Schnider, O. and Grussner, A,; US. Patent 2,676,177; April 20, 1954; assigned to Hoffrnann-La Roche Inc.
water solubility25g/100mLFDA Drug Quality Assessment: Nudexta Dextromethorphan and Quinidine Capsules
Predicted Properties
PropertyValueSource
Water Solubility0.00851 mg/mLALOGPS
logP3.75ALOGPS
logP3.49Chemaxon
logS-4.5ALOGPS
pKa (Strongest Basic)9.85Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area12.47 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity82.56 m3·mol-1Chemaxon
Polarizability31.86 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9959
Blood Brain Barrier+0.9989
Caco-2 permeable+0.8867
P-glycoprotein substrateSubstrate0.8288
P-glycoprotein inhibitor IInhibitor0.654
P-glycoprotein inhibitor IINon-inhibitor0.8383
Renal organic cation transporterInhibitor0.7893
CYP450 2C9 substrateNon-substrate0.8187
CYP450 2D6 substrateSubstrate0.8919
CYP450 3A4 substrateSubstrate0.7783
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8308
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8673
Ames testNon AMES toxic0.5664
CarcinogenicityNon-carcinogens0.9616
BiodegradationNot ready biodegradable0.9763
Rat acute toxicity3.3377 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7107
hERG inhibition (predictor II)Inhibitor0.6723
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Mass Spectrum (Electron Ionization)MSsplash10-00di-5890000000-3009baa7e8a19f9be270
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-0190000000-df99af2429c385c2ac44
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0090000000-1a3ed289b3e93cd6fde4
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0090000000-ebc22884ca50d755e2e4
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0090000000-63612671cfd5e7808f7e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-02mi-0490000000-10cc5d461942becb6194
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-022a-0930000000-943342d8d5a3ae45227f
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0900000000-eb4c5442e33e6921c728
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0090000000-a39a4c295bd6e3b25181
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0090000000-5191ea197708a687222f
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0090000000-3d90a3bd5c1b6788ed43
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-02mi-0490000000-ddc598f28e1a4f9008d1
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-022a-0940000000-cbb4007ab43d33441b69
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00dj-0900000000-457827e6b58fa1a77623
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-0190000000-23c81d81c3ea162f7ab7
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0090000000-1be40c3a6e8dc1309d3d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0090000000-5b655dbdd7f0dfb89568
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00dr-0090000000-843d9ad8469fbcc4b08c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-02tc-2390000000-28393a7b0dcef2929abe
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0090000000-b936a4ab9c28636b57ae
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ita-0290000000-8993598797c0e153c378
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-172.6500572
predicted
DarkChem Lite v0.1.0
[M-H]-163.22635
predicted
DeepCCS 1.0 (2019)
[M+H]+173.2748572
predicted
DarkChem Lite v0.1.0
[M+H]+165.58434
predicted
DeepCCS 1.0 (2019)
[M+Na]+173.0348572
predicted
DarkChem Lite v0.1.0
[M+Na]+172.18437
predicted
DeepCCS 1.0 (2019)

Targets

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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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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. [Article]
  3. 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. [Article]
  4. 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. [Article]
  5. Church AJ, Andrew RD: Spreading depression expands traumatic injury in neocortical brain slices. J Neurotrauma. 2005 Feb;22(2):277-90. [Article]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  7. 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. [Article]
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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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. [Article]
  3. 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. [Article]
  4. 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. [Article]
  5. 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. [Article]
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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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. [Article]
  3. 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. [Article]
  4. 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. [Article]
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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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. [Article]
  3. 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. [Article]
  4. 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. [Article]
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
  1. 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. [Article]
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
  1. 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. [Article]
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
  1. 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. [Article]
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
  1. 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. [Article]
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
  1. 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. [Article]
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
  1. 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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
Regulator
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
  1. 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. [Article]
  2. Raffa RB: A novel approach to the pharmacology of analgesics. Am J Med. 1996 Jul 31;101(1A):40S-46S. doi: 10.1016/s0002-9343(96)00137-4. [Article]
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
  1. 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. [Article]
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
  1. 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. [Article]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Curator comments
This target is based on observed effects of dextromethorphan on reactive oxygen species formation and other downstream pathways.
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
  1. 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. [Article]
  2. Chen CL, Cheng MH, Kuo CF, Cheng YL, Li MH, Chang CP, Wu JJ, Anderson R, Wang S, Tsai PJ, Liu CC, Lin YS: Dextromethorphan Attenuates NADPH Oxidase-Regulated Glycogen Synthase Kinase 3beta and NF-kappaB Activation and Reduces Nitric Oxide Production in Group A Streptococcal Infection. Antimicrob Agents Chemother. 2018 May 25;62(6). pii: AAC.02045-17. doi: 10.1128/AAC.02045-17. Print 2018 Jun. [Article]
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
  1. 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. [Article]

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
  1. 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. [Article]
  2. 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. [Article]
  3. 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. [Article]
  4. 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. [Article]
  5. 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. [Article]
  6. Flockhart Table of Drug Interactions [Link]
  7. Source [Link]
  8. 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
  1. 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. [Article]
  2. 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. [Article]
  3. 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. [Article]
  4. 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
  1. 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. [Article]
  2. 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
  1. 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. [Article]
  2. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
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
  1. 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. [Article]
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
  1. 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. [Article]
  2. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
  3. 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. [Article]
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
  1. 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. [Article]
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
  1. 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. [Article]
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
  1. 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. [Article]
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
  1. 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. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 19, 2024 11:06