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Identification
NameDextromethorphan
Accession NumberDB00514  (APRD00655)
Typesmall molecule
Groupsapproved
Description

The d-isomer of the codeine analog of levorphanol. Dextromethorphan shows high affinity binding to several regions of the brain, including the medullary cough center. This compound is an NMDA receptor antagonist (receptors, N-methyl-D-aspartate) and acts as a non-competitive channel blocker. It is one of the widely used antitussives, and is also used to study the involvement of glutamate receptors in neurotoxicity. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
d-MethorphanNot AvailableNot Available
delta-MethorphanNot AvailableNot Available
DextromethorfanCzechNot Available
DextromethorphanGermanINN
DextrométhorphaneFrenchINN
DextromethorphanumLatinINN
DextrometorfanoSpanishINN
DMNot AvailableIS
DMHMNot AvailableIS
DXMNot AvailableIS
Salts
Name/CAS Structure Properties
Dextromethorphan hydrobromide
Thumb
  • InChI Key: MISZALMBODQYFT-URVXVIKDSA-N
  • Monoisotopic Mass: 351.119777106
  • Average Mass: 352.309
DBSALT000376
Brand names
NameCompany
Balminil DMRougier
Benylin DMMcNeil
DelsymReckitt Benckiser
Koffex DMRougier
RomilarBayer
TriaminicNovartis
Vicks Formula 44Procter & Gamble
Brand mixtures
Brand NameIngredients
Actifed DM SyrupDextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride + Triprolidine Hydrochloride
Actifed DM TabletsDextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride + Triprolidine Hydrochloride
Antitussive Decong Antihistamine SyrDextromethorphan Hydrobromide + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate
Benylin 4 Flu - SyrupAcetaminophen + Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Biohisdex Dm DecongestantDextromethorphan Hydrobromide + Diphenylpyraline Hydrochloride + Phenylephrine Hydrochloride
Biohisdine Dm DecongestantDextromethorphan Hydrobromide + Diphenylpyraline Hydrochloride + Phenylephrine Hydrochloride
Bronchodex Fort-Dm SyrAmmonium Chloride + Dextromethorphan Hydrobromide + Menthol + Pyrilamine Maleate + Sodium Citrate
Bronchodex PediatriqueDextromethorphan Hydrobromide + Guaifenesin + Pheniramine Maleate + Pseudoephedrine Hydrochloride
Bronchosirum Pour EnfantsDextromethorphan Hydrobromide + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate
Calmylin #2 SyrDextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Calmylin #3 SyrDextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Calmylin #4 SyrAmmonium Chloride + Dextromethorphan Hydrobromide + Diphenhydramine Hydrochloride
Calmylin Cough and Flu LiqAcetaminophen + Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Calmylin Pediatric SyrupDextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Centracol DM - SyrDextromethorphan Hydrobromide + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate
Centracol Pediatrique - SyrDextromethorphan Hydrobromide + Guaifenesin + Pheniramine Maleate + Pseudoephedrine Hydrochloride
Chemhisdex Dm DecongestantDextromethorphan Hydrobromide + Diphenylpyraline Hydrochloride + Phenylephrine Hydrochloride
Chemhisdine Dm DecongestantDextromethorphan Hydrobromide + Diphenylpyraline Hydrochloride + Phenylephrine Hydrochloride
Children's Tussin Cough Medicine Dm Antitussive DecongestantDextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Children's Tylenol Cold Liquid with DmAcetaminophen + Chlorpheniramine Maleate + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Citron Chaud Dm Cumberland PwsDextromethorphan Hydrobromide + Pheniramine Maleate + Phenylephrine Hydrochloride + Vitamin C
Cold Relief DmBrompheniramine Maleate + Dextromethorphan Hydrobromide + Phenylpropanolamine Hydrochloride
Cold/Flu ReliefAcetaminophen + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Contac Cough Cold and Flu CapletsAcetaminophen + Chlorpheniramine Maleate + Dextromethorphan Hydrobromide + Phenylpropanolamine Hydrochloride
Cough and Flu SyrupAcetaminophen + Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Cough Syrup Dm DecongestantDextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Cough Syrup Dm Decongestant ExpectorantDextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Cough Syrup Dm Decongestant for ChildrenDextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Cough Syrup Dm ExpectorantDextromethorphan Hydrobromide + Guaifenesin
Cough Syrup Dm-D-EDextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Cough Syrup Dm-EDextromethorphan Hydrobromide + Guaifenesin
Cough Syrup Dm-ExpectorantDextromethorphan Hydrobromide + Guaifenesin
Cough Syrup W.Guaifenesin W.DextromethorphanDextromethorphan Hydrobromide + Guaifenesin
Cough, Cold & Allergy ReliefBrompheniramine Maleate + Dextromethorphan Hydrobromide + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Dayquil LiquicapsAcetaminophen + Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Dayquil Liquicaps - CapAcetaminophen + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Dayquil Medicine - LiqAcetaminophen + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Daytime Cold & Flu Liquid CapsulesAcetaminophen + Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Daytime Liquid - LiqAcetaminophen + Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Demdec SyrDextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Dimetapp Children's Cough and Cold LiquidDextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Dimetapp Cough & Cold Liqui-Gels - CapBrompheniramine Maleate + Dextromethorphan Hydrobromide + Phenylpropanolamine Hydrochloride
Dimetapp Cough, Cold & FluAcetaminophen + Brompheniramine Maleate + Dextromethorphan Hydrobromide + Phenylpropanolamine Hydrochloride
Dimetapp Dm ElixirBrompheniramine Maleate + Dextromethorphan Hydrobromide + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Dimetapp Dm TabBrompheniramine Maleate + Dextromethorphan Hydrobromide + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride
Dm Cough SyrAmmonium Chloride + Dextromethorphan Hydrobromide + Diphenhydramine Hydrochloride
Dm Cough Syrup DecongestantDextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Dm Cough Syrup ExpectorantDextromethorphan Hydrobromide + Guaifenesin
Dm Expectorant Cough SyrupDextromethorphan Hydrobromide + Guaifenesin
Dm Plus Cough SyrupAmmonium Chloride + Dextromethorphan Hydrobromide + Diphenhydramine Hydrochloride
Dm Plus Decongestant Cough SyrupDextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Dm Plus Decongestant Plus Expector.Ex.St.SyrDextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Dm Plus Decongestant Plus Expectorant Cough SyrupDextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Dm Plus Expectorant SyrupDextromethorphan Hydrobromide + Guaifenesin
Dm SyrupAmmonium Chloride + Dextromethorphan Hydrobromide + Diphenhydramine Hydrochloride
Dm-D-Expectorant Cough and Cold SyrupDextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Extra Strength Cold Medication Daytime RlfAcetaminophen + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Extra Strength Daytime Cold Relief-CapletAcetaminophen + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Extra Strength Nighttime Cold Relief-CapletAcetaminophen + Chlorpheniramine Maleate + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Extra Strength Tylenol Cold and Flu PowderAcetaminophen + Chlorpheniramine Maleate + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Hot Lemon Relief Dm AdultDextromethorphan Hydrobromide + Pheniramine Maleate + Phenylephrine Hydrochloride
Koffex Dm + Decongestant + ExpectorantDextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Koffex Dm + Decongestant + Expectorant Extra StrengthDextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Koffex Dm + Decongestant SyrupDextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Koffex Dm + ExpectorantDextromethorphan Hydrobromide + Guaifenesin
Koffex Dm + Expectorant Extra StrengthDextromethorphan Hydrobromide + Guaifenesin
Koffex Dm-D-E - LiqDextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
MetrateDextromethorphan Hydrobromide + Diphenylpyraline Hydrochloride + Potassium Iodide + Sodium Citrate
Mucinex DMDextromethorphan and Guaifenesin
Neo Citran Daycaps Extra Strength - CapletAcetaminophen + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Nighttime Cold and Flu Liquid CapsulesAcetaminophen + Dextromethorphan Hydrobromide + Doxylamine Succinate + Pseudoephedrine Hydrochloride
Nighttime Cold and Flu ReliefAcetaminophen + Dextromethorphan Hydrobromide + Doxylamine Succinate + Pseudoephedrine Hydrochloride
Nitetime Cold MedicineAcetaminophen + Dextromethorphan Hydrobromide + Doxylamine Succinate + Pseudoephedrine Hydrochloride
Novahistex Dm Expectorant with DecongestantDextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Novahistex Dm with DecongestantDextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Novahistine Dm Expectorant with DecongestantDextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Novahistine Dm with Decongestant - LiqDextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Nyquil LiquicapsAcetaminophen + Dextromethorphan Hydrobromide + Doxylamine Succinate + Pseudoephedrine Hydrochloride
Ornade Dm 10 LiqChlorpheniramine Maleate + Dextromethorphan Hydrobromide + Phenylpropanolamine Hydrochloride
Ornade Dm 15 LiqChlorpheniramine Maleate + Dextromethorphan Hydrobromide + Phenylpropanolamine Hydrochloride
Ornade Dm 30 LiqChlorpheniramine Maleate + Dextromethorphan Hydrobromide + Phenylpropanolamine Hydrochloride
Pediatric Cough SyrupDextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Personnelle Dm SyrDextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Pharmacol Dm SyrDextromethorphan Hydrobromide + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate
Pharminicol Dm SyrupDextromethorphan Hydrobromide + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate
Pharmitussin DmDextromethorphan Hydrobromide + Guaifenesin
Promatussin Dm Adult Formula SyrDextromethorphan Hydrobromide + Promethazine Hydrochloride + Pseudoephedrine Hydrochloride
Promatussin Dm Children FormulaDextromethorphan Hydrobromide + Promethazine Hydrochloride + Pseudoephedrine Hydrochloride
Reg.Str.Cold Medic.Night Time Relief)Caplet (Acetaminophen + Chlorpheniramine Maleate + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Regular Strength Cold MedicationDaytime R.) (Acetaminophen + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Regular Strength Tylenol Cold and Flu PowderAcetaminophen + Chlorpheniramine Maleate + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Regular Strength Tylenol Cold Chest CongestionAcetaminophen + Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Regular Strength Tylenol Cough SuspensionAcetaminophen + Dextromethorphan Hydrobromide
Regular Strength Tylenol Cough Suspension with DecongestantAcetaminophen + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Robitussin DMDextromethorphan and Guaifenesin
Robitussin Honey Cough and ColdDextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Robitussin Honey FluAcetaminophen + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Sudafed Cold and Cough Extra Strength CapletAcetaminophen + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Sudafed Cold and Flu Gel CapsAcetaminophen + Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Sudafed DmDextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Tantacol Dm SyrDextromethorphan Hydrobromide + Pheniramine Maleate + Phenylpropanolamine Hydrochloride + Pyrilamine Maleate
Theraflu Flu Cold and Cough MedicineAcetaminophen + Chlorpheniramine Maleate + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Triaminic Dm Daytime SyrDextromethorphan Hydrobromide + Guaifenesin + Phenylpropanolamine Hydrochloride
Triaminic Dm Expectorant SyrChlorpheniramine Maleate + Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Triaminic Dm Plus Decongestant SyrupDextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Triaminic Dm+Decongestant Liqui-Gels CapsulesDextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Triaminicol Dm SyrupChlorpheniramine Maleate + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride
Tussin Cough Medicine Dm Antitussive Expectorant DecongestantDextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride
Categories
CAS number125-71-3
WeightAverage: 271.3972
Monoisotopic: 271.193614427
Chemical FormulaC18H25NO
InChI KeyInChIKey=MKXZASYAUGDDCJ-HPAQEFICNA-N
InChI
InChI=1/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+/s2
IUPAC Name
(1R,9R,10R)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-triene
SMILES
[H][C@@]12CCCC[C@@]11CCN(C)[C@@H]2CC2=C1C=C(OC)C=C2
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassAlkaloids and Derivatives
ClassMorphinans
SubclassNot Available
Direct parentMorphinans
Alternative parentsBenzylisoquinolines; Phenanthrenes and Derivatives; Tetralins; Anisoles; Alkyl Aryl Ethers; Piperidines; Tertiary Amines; Polyamines
Substituentsphenanthrene; tetralin; anisole; phenol ether; alkyl aryl ether; benzene; piperidine; tertiary amine; polyamine; ether; amine; organonitrogen compound
Classification descriptionThis compound belongs to the 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.
Pharmacology
IndicationFor treatment and relief of dry cough.
PharmacodynamicsDextromethorphan suppresses the cough reflex by a direct action on the cough center in the medulla of the brain. Dextromethorphan shows high affinity binding to several regions of the brain, including the medullary cough center. This compound is an NMDA receptor antagonist and acts as a non-competitive channel blocker. It is one of the widely used antitussives, and is also used to study the involvement of glutamate receptors in neurotoxicity.
Mechanism of actionDextromethorphan is an opioid-like drug that binds to and acts as antagonist to the NMDA glutamatergic receptor, it is an agonist to the opioid sigma 1 and sigma 2 receptors, it is also an alpha3/beta4 nicotinic receptor antagonist and targets the serotonin reuptake pump. Dextromethorphan is rapidly absorbed from the gastrointestinal tract, where it enters the bloodstream and crosses the blood-brain barrier. The first-pass through the hepatic portal vein results in some of the drug being metabolized into an active metabolite of dextromethorphan, dextrorphan, the 3-hydroxy derivative of dextromethorphan.
AbsorptionRapidly absorbed from the gastrointestinal tract.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic. Rapidly and extensively metabolized to dextrorphan (active metabolite). One well known metabolic catalyst involved is a specific cytochrome P450 enzyme known as 2D6, or CYP2D6.

SubstrateEnzymesProduct
Dextromethorphan
DextrorphanDetails
Dextromethorphan
3-MethoxymorphinanDetails
Dextrorphan
Dextrorphan O-glucuronideDetails
Dextrorphan
    Dextrorphan sulfateDetails
    Dextrorphan
    3-HydroxymorphinanDetails
    3-Hydroxymorphinan
    3-Hydroxymorphinan O-glucuronideDetails
    3-Hydroxymorphinan
      3-Hydroxymorphinan sulfateDetails
      3-Methoxymorphinan
      3-HydroxymorphinanDetails
      Route of eliminationNot Available
      Half life3-6 hours
      ClearanceNot Available
      ToxicityNot Available
      Affected organisms
      • Humans and other mammals
      PathwaysNot Available
      SNP Mediated Effects
      Interacting Gene/EnzymeSNP RS IDAllele nameDefining changeEffectReference(s)
      Cytochrome P450 2D6
      Gene symbol: CYP2D6
      UniProt: P10635
      rs3892097 CYP2D6*4A Allele, homozygotePoor drug metabolizer, lower dose requirements10513455
      Cytochrome P450 2D6
      Gene symbol: CYP2D6
      UniProt: P10635
      rs5030655 CYP2D6*6T deletion, homozygotePoor drug metabolizer, lower dose requirements10513455
      SNP Mediated Adverse Drug ReactionsNot Available
      ADMET
      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 substrate Non-inhibitor 0.9071
      CYP450 2D6 substrate Inhibitor 0.8932
      CYP450 2C19 substrate Non-inhibitor 0.9025
      CYP450 3A4 substrate 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
      Pharmacoeconomics
      Manufacturers
      • Reckitt benckiser
      Packagers
      Dosage forms
      FormRouteStrength
      CapsuleOral
      LiquidOral
      LozengeOral
      StripOral
      SuspensionOral
      SyrupOral
      TabletOral
      Prices
      Unit descriptionCostUnit
      Modicon (28) 28 0.5-35 mg-mcg tablet Disp Pack59.99USDdisp
      Dextromethorphan powder14.93USDg
      Dextromethorphan hbr powder4.74USDg
      Dextromethorphan hbr cryst2.06USDg
      Triaminic allergy thin strip0.35USDstrip
      Triaminic cold-stuff nose strip0.35USDstrip
      Triaminic cgh-runny nose strip0.3USDeach
      Triaminic cough strips0.3USDstrip
      Triaminic cough-cold chew0.27USDeach
      Triaminic softchew tablet0.27USDtablet
      Robitussin coughgels0.25USDeach
      Triaminic softchews tablet0.25USDtablet
      Childrens triaminic decon spray0.24USDml
      Hold 4 hour lozenge regular0.24USDlozenge
      Hca severe cough stopper cplet0.23USDeach
      Triaminicin tablet0.23USDtablet
      Delsym 30 mg/5 ml suspension0.11USDml
      Robitussin dm to go liquid0.09USDml
      Apap allergy sinus caplet0.05USDcaplet
      Adlt robitussin cough-cold-flu0.04USDml
      Adt robitussin cough-cold d lq0.04USDml
      Adult robitussin cough syrup0.04USDml
      Robitussin chest congest syrup0.04USDml
      Robitussin cough & cold liquid0.04USDml
      Robitussin cough-cold liquid0.04USDml
      Robitussin cough-cong syrup0.04USDml
      Robitussin dm max liquid0.04USDml
      Robitussin long-acting liq0.04USDml
      Robitussin pe head & chest liq0.04USDml
      Robitussin-cough-chest-cong lq0.04USDml
      Robitussin-dm cough syrup0.04USDml
      Triaminic chest-nasal cong liq0.04USDml
      Triaminic cold & cough liquid0.04USDml
      Triaminic cold-allergy pe liq0.04USDml
      Triaminic cough-nasal cong liq0.04USDml
      Triaminic cough-sore throat lq0.04USDml
      Triaminic flu cough-fever susp0.04USDml
      Triaminic flu-cough-fever liq0.04USDml
      Triaminic-d syrup0.04USDml
      Vicks 44 cough liquid0.03USDml
      Vicks 44 custom care liquid0.03USDml
      Guaifenesin dm syrup0.02USDml
      DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
      Patents
      CountryPatent NumberApprovedExpires (estimated)
      United States59808821997-04-162017-04-16
      Properties
      Statesolid
      Experimental Properties
      PropertyValueSource
      water solubility74.7 mg/LNot Available
      logP3.6Not Available
      Predicted Properties
      PropertyValueSource
      water solubility8.51e-03 g/lALOGPS
      logP3.75ALOGPS
      logP3.49ChemAxon
      logS-4.5ALOGPS
      pKa (strongest basic)9.85ChemAxon
      physiological charge1ChemAxon
      hydrogen acceptor count2ChemAxon
      hydrogen donor count0ChemAxon
      polar surface area12.47ChemAxon
      rotatable bond count1ChemAxon
      refractivity82.56ChemAxon
      polarizability31.74ChemAxon
      number of rings4ChemAxon
      bioavailability1ChemAxon
      rule of fiveYesChemAxon
      Ghose filterYesChemAxon
      Veber's ruleYesChemAxon
      MDDR-like ruleNoChemAxon
      Spectra
      SpectraNot Available
      References
      Synthesis Reference

      Mahendra R. Patel, “Sustained Release Suspension Preparation For Dextromethorphan.” U.S. Patent US20130115253, issued May 09, 2013.

      US20130115253
      General Reference
      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. Pubmed
      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. Pubmed
      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. Pubmed
      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. Pubmed
      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. Pubmed
      External Links
      ResourceLink
      KEGG DrugD03742
      KEGG CompoundC06947
      ChEBI4470
      ChEMBLCHEMBL52440
      Therapeutic Targets DatabaseDNC000541
      PharmGKBPA449273
      Drug Product Database816000
      Drugs.comhttp://www.drugs.com/dextromethorphan.html
      WikipediaDextromethorphan
      ATC CodesR05DA09
      AHFS Codes
      • 48:16.00
      • 48:08.00
      PDB EntriesNot Available
      FDA labelNot Available
      MSDSshow(73.3 KB)
      Interactions
      Drug Interactions
      Drug
      AbirateroneAbiraterone increases levels by affecting CYP2D6 metabolism. Interaction is significant so monitor closely.
      DesvenlafaxineIncreased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
      Dihydroquinidine barbiturateQuinidine increases the toxicity of dextromethorphan
      FluoxetineCombination associated with possible serotoninergic syndrome
      IsocarboxazidPossible severe adverse reaction
      MoclobemideIncreased CNS toxicity
      ParoxetineCombination associated with possible serotoninergic syndrome
      PhenelzinePossible severe adverse reaction
      QuinidineQuinidine increases the toxicity of dextromethorphan
      Quinidine barbiturateQuinidine increases the toxicity of dextromethorphan
      RasagilinePossible severe adverse reaction
      SelegilineCombination associated with possible serotoninergic syndrome
      SibutramineCombination associated with possible serotoninergic syndrome
      TerbinafineTerbinafine may reduce the metabolism and clearance of Dextromethorphan. Consider alternate therapy or monitor for therapeutic/adverse effects of Dextromethorphan if Terbinafine is initiated, discontinued or dose changed.
      TocilizumabDextromethorphan is a CYP2D6 and CYP3A4 substrate. Exposure of dextromethorphan decreases following administration of tocilizumab.
      TramadolIncreased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
      TranylcypromineIncreased risk of serotonin syndrome. Concomitant use should be avoided.
      TrazodoneIncreased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
      TrimipramineIncreased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
      VemurafenibVemurafenib increases the AUC (CYP2D6 substrate) by 47% .
      VenlafaxineIncreased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
      VilazodoneConsideration should be given to avoiding the concomitant use of dextromethorphan and selective serotonin reuptake inhibitors (SSRI). Monitor for toxic effects of dextromethorphan (eg, CNS, Cardiovascular) if an SSRI is initiated or the dose is increased. SSRIs, other than fluoxetine and paroxetine, may be safer alternatives due to lesser CYP2D6 inhibition; however, the mechanism for the interaction is not fully understood, and caution is still advised.
      ZolmitriptanUse of two serotonin modulators, such as zolmitriptan and dextromethorphan, increases the risk of serotonin syndrome. Consider alternate therapy or monitor for serotonin syndrome during concomitant therapy.
      Food Interactions
      • Take without regard to meals.

      1. Sigma non-opioid intracellular receptor 1

      Kind: protein

      Organism: Human

      Pharmacological action: yes

      Actions: agonist

      Components

      Name UniProt ID Details
      Sigma non-opioid intracellular receptor 1 Q99720 Details

      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. Pubmed
      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. Pubmed
      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. Pubmed
      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. Pubmed
      5. Church AJ, Andrew RD: Spreading depression expands traumatic injury in neocortical brain slices. J Neurotrauma. 2005 Feb;22(2):277-90. Pubmed
      6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

      2. HCG20471, isoform CRA_c

      Kind: protein

      Organism: Human

      Pharmacological action: yes

      Actions: agonist

      Components

      Name UniProt ID Details
      HCG20471, isoform CRA_c Q5T1J1 Details

      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. Pubmed
      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. Pubmed
      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. Pubmed

      3. Glutamate receptor ionotropic, NMDA 3A

      Kind: protein

      Organism: Human

      Pharmacological action: yes

      Actions: antagonist

      Components

      Name UniProt ID Details
      Glutamate receptor ionotropic, NMDA 3A Q8TCU5 Details

      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. Pubmed
      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. Pubmed
      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. Pubmed
      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. Pubmed
      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. Pubmed

      4. Neuronal acetylcholine receptor subunit alpha-2

      Kind: protein

      Organism: Human

      Pharmacological action: unknown

      Actions: antagonist

      Components

      Name UniProt ID Details
      Neuronal acetylcholine receptor subunit alpha-2 Q15822 Details

      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. Pubmed
      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. Pubmed
      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. Pubmed
      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. Pubmed

      5. Sodium-dependent serotonin transporter

      Kind: protein

      Organism: Human

      Pharmacological action: unknown

      Actions: inhibitor

      Components

      Name UniProt ID Details
      Sodium-dependent serotonin transporter P31645 Details

      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. Pubmed
      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. Pubmed
      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. Pubmed
      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. Pubmed

      1. Cytochrome P450 3A4

      Kind: protein

      Organism: Human

      Pharmacological action: unknown

      Actions: substrate

      Components

      Name UniProt ID Details
      Cytochrome P450 3A4 P08684 Details

      References:

      1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
      2. 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
      3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
      4. 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

      2. Cytochrome P450 2D6

      Kind: protein

      Organism: Human

      Pharmacological action: unknown

      Actions: substrate inhibitor

      Components

      Name UniProt ID Details
      Cytochrome P450 2D6 P10635 Details

      References:

      1. Zhou SF: Polymorphism of human cytochrome P450 2D6 and its clinical significance: Part I. Clin Pharmacokinet. 2009;48(11):689-723. Pubmed
      2. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
      3. 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
      4. © Tianyi Zhang, Yongxin Zhu, and Chandrani Gunaratna. Simultaneous Determination of Metabolites from Multiple Cytochrome P450 Probe Substrates by Gradient Liquid Chromatography with UV Detection. Source
      5. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
      6. 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
      7. 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

      3. Cytochrome P450 3A5

      Kind: protein

      Organism: Human

      Pharmacological action: unknown

      Actions: substrate

      Components

      Name UniProt ID Details
      Cytochrome P450 3A5 P20815 Details

      References:

      1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
      2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

      4. Cytochrome P450 3A7

      Kind: protein

      Organism: Human

      Pharmacological action: unknown

      Actions: substrate

      Components

      Name UniProt ID Details
      Cytochrome P450 3A7 P24462 Details

      References:

      1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
      2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

      5. Cytochrome P450 2B6

      Kind: protein

      Organism: Human

      Pharmacological action: unknown

      Actions: substrate

      Components

      Name UniProt ID Details
      Cytochrome P450 2B6 P20813 Details

      References:

      1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
      2. 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

      6. Cytochrome P450 2C19

      Kind: protein

      Organism: Human

      Pharmacological action: unknown

      Actions: substrate

      Components

      Name UniProt ID Details
      Cytochrome P450 2C19 P33261 Details

      References:

      1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

      7. Cytochrome P450 2C9

      Kind: protein

      Organism: Human

      Pharmacological action: unknown

      Actions: substrate

      Components

      Name UniProt ID Details
      Cytochrome P450 2C9 P11712 Details

      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. Pubmed
      2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

      8. Cytochrome P450 2C8

      Kind: protein

      Organism: Human

      Pharmacological action: unknown

      Actions: substrate

      Components

      Name UniProt ID Details
      Cytochrome P450 2C8 P10632 Details

      References:

      1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

      9. Cytochrome P450 2E1

      Kind: protein

      Organism: Human

      Pharmacological action: unknown

      Actions: substrate

      Components

      Name UniProt ID Details
      Cytochrome P450 2E1 P05181 Details

      References:

      1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

      1. Multidrug resistance protein 1

      Kind: protein

      Organism: Human

      Pharmacological action: unknown

      Actions: inhibitor

      Components

      Name UniProt ID Details
      Multidrug resistance protein 1 P08183 Details

      References:

      1. Wang E, Lew K, Barecki M, Casciano CN, Clement RP, Johnson WW: Quantitative distinctions of active site molecular recognition by P-glycoprotein and cytochrome P450 3A4. Chem Res Toxicol. 2001 Dec;14(12):1596-603. Pubmed

      Comments
      Drug created on June 13, 2005 07:24 / Updated on November 22, 2013 14:24