Dextromethorphan

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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

Similar Structures

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

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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 Type	Indication	Combined Product Details	Approval Level	Dose Form
Used in combination to treat	Allergic cough	Combination Product in combination with: Terpin hydrate (DB13163), Chlorpheniramine (DB01114)	••••••••••••	••••••• ••••••• ••••••
Used in combination for symptomatic treatment of	Common cold	Combination Product in combination with: Phenylephrine (DB00388), Chlorpheniramine (DB01114), Ibuprofen (DB01050)	••• •••	•••••••• •••••• ••••••
Used in combination for symptomatic treatment of	Common cold	Combination Product in combination with: Acetaminophen (DB00316), Chlorpheniramine (DB01114)	••• •••
Used in combination for symptomatic treatment of	Common cold	Combination Product in combination with: Pseudoephedrine (DB00852), Diphenhydramine (DB01075), Guaifenesin (DB00874)	••••••••••••	•••••••• •••••••• • •••••• •••••
Used in combination for symptomatic treatment of	Common cold	Combination 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 a low-affinity uncompetitive NMDA antagonist and sigma-1 receptor agonist.¹³ It is also an antagonist of α3/β4 nicotinic receptors.¹² However, the mechanism by which dextromethorphan's receptor agonism and antagonism translate to a clinical effect is not well understood.⁹

Target	Actions	Organism
ASigma non-opioid intracellular receptor 1	agonist	Humans
AAromatase	inhibitor	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 C_max of 2.9 ng/mL, with a T_max 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

Hover over products below to view reaction partners

Dextromethorphan
- Dextrorphan
- (+)-3-Methoxymorphinan
  - 3-Hydroxymorphinan

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/Enzyme	Allele name	Genotype(s)	Defining Change(s)	Type(s)	Description	Details
Cytochrome P450 2D6	CYP2D6*4	(A;A)	A Allele, homozygote	Effect Directly Studied	Patients with this genotype have reduced metabolism of dextromethorphan.	Details
Cytochrome P450 2D6	CYP2D6*6	(-;-)	T deletion, homozygote	Effect Directly Studied	Patients with this genotype have reduced metabolism of dextromethorphan.	Details
Cytochrome P450 2D6	CYP2D6*3	Not Available	C allele	Effect Inferred	Poor drug metabolizer, lower dose requirements	Details
Cytochrome P450 2D6	CYP2D6*5	Not Available	Whole-gene deletion	Effect Inferred	Poor drug metabolizer, lower dose requirements	Details
Cytochrome P450 2D6	CYP2D6*7	Not Available	2935A>C	Effect Inferred	Poor drug metabolizer, lower dose requirements	Details
Cytochrome P450 2D6	CYP2D6*8	Not Available	1758G>T	Effect Inferred	Poor drug metabolizer, lower dose requirements	Details
Cytochrome P450 2D6	CYP2D6*11	Not Available	883G>C	Effect Inferred	Poor drug metabolizer, lower dose requirements	Details
Cytochrome P450 2D6	CYP2D6*12	Not Available	124G>A	Effect Inferred	Poor drug metabolizer, lower dose requirements	Details
Cytochrome P450 2D6	CYP2D6*13	Not Available	CYP2D7/2D6 hybrid gene structure	Effect Inferred	Poor drug metabolizer, lower dose requirements	Details
Cytochrome P450 2D6	CYP2D6*14A	Not Available	1758G>A	Effect Inferred	Poor drug metabolizer, lower dose requirements	Details
Cytochrome P450 2D6	CYP2D6*15	Not Available	137insT, 137_138insT	Effect Inferred	Poor drug metabolizer, lower dose requirements	Details
Cytochrome P450 2D6	CYP2D6*19	Not Available	2539_2542delAACT	Effect Inferred	Poor drug metabolizer, lower dose requirements	Details
Cytochrome P450 2D6	CYP2D6*20	Not Available	1973_1974insG	Effect Inferred	Poor drug metabolizer, lower dose requirements	Details
Cytochrome P450 2D6	CYP2D6*21	Not Available	2573insC	Effect Inferred	Poor drug metabolizer, lower dose requirements	Details
Cytochrome P450 2D6	CYP2D6*31	Not Available	-1770G>A / -1584C>G … show all	Effect Inferred	Poor drug metabolizer, lower dose requirements	Details
Cytochrome P450 2D6	CYP2D6*36	Not Available	100C>T / -1426C>T … show all	Effect Inferred	Poor drug metabolizer, lower dose requirements	Details
Cytochrome P450 2D6	CYP2D6*38	Not Available	2587_2590delGACT	Effect Inferred	Poor drug metabolizer, lower dose requirements	Details
Cytochrome P450 2D6	CYP2D6*40	Not Available	1863_1864ins(TTT CGC CCC)2	Effect Inferred	Poor drug metabolizer, lower dose requirements	Details
Cytochrome P450 2D6	CYP2D6*42	Not Available	3259_3260insGT	Effect Inferred	Poor drug metabolizer, lower dose requirements	Details
Cytochrome P450 2D6	CYP2D6*44	Not Available	2950G>C	Effect Inferred	Poor drug metabolizer, lower dose requirements	Details
Cytochrome P450 2D6	CYP2D6*47	Not Available	100C>T / -1426C>T … show all	Effect Inferred	Poor drug metabolizer, lower dose requirements	Details
Cytochrome P450 2D6	CYP2D6*51	Not Available	-1584C>G / -1235A>G … show all	Effect Inferred	Poor drug metabolizer, lower dose requirements	Details
Cytochrome P450 2D6	CYP2D6*56	Not Available	3201C>T	Effect Inferred	Poor drug metabolizer, lower dose requirements	Details
Cytochrome P450 2D6	CYP2D6*57	Not Available	100C>T / 310G>T … show all	Effect Inferred	Poor drug metabolizer, lower dose requirements	Details
Cytochrome P450 2D6	CYP2D6*62	Not Available	4044C>T	Effect Inferred	Poor drug metabolizer, lower dose requirements	Details
Cytochrome P450 2D6	CYP2D6*68A	Not Available	-1426C>T / -1235A>G … show all	Effect Inferred	Poor drug metabolizer, lower dose requirements	Details
Cytochrome P450 2D6	CYP2D6*68B	Not Available	Similar but not identical switch region compared to CYP2D668A. Found in tandem arrangement with CYP2D64.	Effect Inferred	Poor drug metabolizer, lower dose requirements	Details
Cytochrome P450 2D6	CYP2D6*69	Not Available	2988G>A / -1426C>T … show all	Effect Inferred	Poor drug metabolizer, lower dose requirements	Details
Cytochrome P450 2D6	CYP2D6*92	Not Available	1995delC	Effect Inferred	Poor drug metabolizer, lower dose requirements	Details
Cytochrome P450 2D6	CYP2D6*100	Not Available	-1426C>T / -1235A>G … show all	Effect Inferred	Poor drug metabolizer, lower dose requirements	Details
Cytochrome P450 2D6	CYP2D6*101	Not Available	-1426C>T / -1235A>G … show all	Effect Inferred	Poor drug metabolizer, lower dose requirements	Details

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
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1,2-Benzodiazepine	The risk or severity of CNS depression can be increased when Dextromethorphan is combined with 1,2-Benzodiazepine.
Abametapir	The serum concentration of Dextromethorphan can be increased when it is combined with Abametapir.
Abatacept	The metabolism of Dextromethorphan can be increased when combined with Abatacept.
Abiraterone	The metabolism of Dextromethorphan can be decreased when combined with Abiraterone.
Abrocitinib	The 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

Ingredient	UNII	CAS	InChI Key
Dextromethorphan hydriodide	086F8ZEM77	7487-74-3	RWSHVMCJJPXQSP-URVXVIKDSA-N
Dextromethorphan hydrobromide	Z0CG3115FG	125-69-9	MISZALMBODQYFT-URVXVIKDSA-N
Dextromethorphan hydrobromide monohydrate	9D2RTI9KYH	6700-34-1	STTADZBLEUMJRG-IKNOHUQMSA-N
Dextromethorphan hydrochloride	351KFH969D	18609-21-7	SNDDIRAXSDUVKW-URVXVIKDSA-N

Active Moieties

Name	Kind	UNII	CAS	InChI Key
Dextrorphan	prodrug	04B7QNO9WS	125-73-5	JAQUASYNZVUNQP-PVAVHDDUSA-N

Product Images

International/Other Brands

Benylin DM (McNeil) / Romilar (Bayer) / Triaminic (Novartis) / Vicks Formula 44 (Procter & Gamble)

Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
12 Hour Cough Relief	Suspension	30 mg/5mL	Oral	Western Family Foods	2013-07-03	2017-04-01
12 Hour Cough Relief	Suspension	30 mg/5mL	Oral	Western Family Foods	2012-09-14	2017-05-01
7 Select Cough DM	Suspension	30 mg/5mL	Oral	7 Eleven	2014-09-05	2016-10-01
Adult Cough Relief DM	Liquid	30 mg/10mL	Oral	Safeway, Inc.	2014-06-30	2025-06-30
Adult Honey Works	Syrup	5 mg / 5 mL	Oral	Lifelab Health Llc	2018-10-09	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
24/7 Life Cold and Flu DayTime Severe	Dextromethorphan hydrobromide monohydrate (10 mg/1) + Acetaminophen (325 mg/1) + Guaifenesin (200 mg/1) + Phenylephrine hydrochloride (5 mg/1)	Tablet, film coated	Oral	Lil' Drug Store Products, Inc.	2021-10-27	Not applicable
7 Select Day Time Relief	Dextromethorphan hydrobromide monohydrate (10 mg/15mL) + Acetaminophen (325 mg/15mL) + Phenylephrine hydrochloride (5 mg/15mL)	Solution	Oral	7-Eleven	2014-08-05	2020-10-31
7 Select Day Time Relief	Dextromethorphan hydrobromide monohydrate (10 mg/1) + Acetaminophen (325 mg/1) + Phenylephrine hydrochloride (5 mg/1)	Capsule, liquid filled	Oral	7-Eleven	2014-04-22	2020-01-31
7 Select Maximum Strength	Dextromethorphan hydrobromide monohydrate (20 mg/20mL) + Guaifenesin (400 mg/20mL)	Solution	Oral	7-Eleven	2019-03-25	Not applicable
7 Select Night Time Relief	Dextromethorphan hydrobromide monohydrate (15 mg/1) + Acetaminophen (325 mg/1) + Doxylamine succinate (6.25 mg/1)	Capsule, liquid filled	Oral	7-Eleven	2014-04-17	2020-07-31

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Alahist DM	Dextromethorphan hydrobromide monohydrate (10 mg/5mL) + Pheniramine maleate (12.5 mg/5mL) + Phenylephrine hydrochloride (5 mg/5mL)	Liquid	Oral	Poly Pharmaceuticals, Inc.	2023-06-08	Not applicable
Aquanaz	Dextromethorphan hydrobromide monohydrate (15 mg/1) + Guaifenesin (400 mg/1) + Phenylephrine hydrochloride (10 mg/1)	Tablet	Oral	Capital Pharmaceutical, LLC	2015-03-10	Not applicable
Atuss DS Tannate Suspension	Dextromethorphan hydrobromide monohydrate (30 mg/5mL) + Chlorpheniramine maleate (4 mg/5mL) + Pseudoephedrine hydrochloride (30 mg/5mL)	Suspension	Oral	Atley Pharmaceuticals	2006-11-21	Not applicable
BPM Mal Phenyleph HCl DM HBr	Dextromethorphan hydrobromide monohydrate (20 mg/5mL) + Brompheniramine maleate (4 mg/5mL) + Phenylephrine hydrochloride (10 mg/5mL)	Liquid	Oral	River's Edge Pharmaceuticals, LLC	2010-01-18	2012-01-31
Brom Mal Phenyl HCl Dex HBr	Dextromethorphan hydrobromide monohydrate (15 mg/5mL) + Brompheniramine maleate (4 mg/5mL) + Phenylephrine hydrochloride (7.5 mg/5mL)	Liquid	Oral	River's Edge Pharmaceuticals, LLC	2010-02-10	2012-02-29

Chemical Identifiers

UNII: 7355X3ROTS
CAS number: 125-71-3
InChI Key: MKXZASYAUGDDCJ-NJAFHUGGSA-N
InChI: InChI=1S/C18H25NO/c1-19-10-9-18-8-4-3-5-15(18)17(19)11-13-6-7-14(20-2)12-16(13)18/h6-7,12,15,17H,3-5,8-11H2,1-2H3/t15-,17+,18+/m1/s1
IUPAC Name: (1S,9S,10S)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,5-triene
SMILES: [H][C@]12CCCC[C@]11CCN(C)[C@H]2CC2=C1C=C(OC)C=C2

References

Synthesis Reference

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

US20130115253

General References

Brooks BR, Thisted RA, Appel SH, Bradley WG, Olney RK, Berg JE, Pope LE, Smith RA: Treatment of pseudobulbar affect in ALS with dextromethorphan/quinidine: a randomized trial. Neurology. 2004 Oct 26;63(8):1364-70. [Article]
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]
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]
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]
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]
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]
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]
Journey JD, Agrawal S, Stern E: Dextromethorphan Toxicity . [Article]
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]
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]
Oh SR, Agrawal S, Sabir S, Taylor A: Dextromethorphan . [Article]
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]
FDA Approved Drug Products: Nuedexta Dextromethorphan Hydrobromide and Quinidine Sulfate Oral Capsules [Link]
Dailymed: Brompheniramine, Pseudoephedrine, and Dextromethorphan Oral Syrup [Link]
Dailymed: Guaifenesin and Dextromethorphan Oral Extended Release Tablets [Link]
FDA Drug Quality Assessment: Nuedexta Dextromethorphan and Quinidine Capsules [Link]
FDA Approved Drug Products: Promethazine Hydrochloride and Dextromethorphan Hydrobromide Oral Syrup (Discontinued) [Link]
FDA Approved Drug Products: AUVELITY (dextromethorphan hydrobromide and bupropion hydrochloride) extended-release tablets, for oral use [Link]

External Links

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

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Phase	Status	Purpose	Conditions	Count	Start Date	Why Stopped	100+ additional columns
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Not Available	Not Yet Recruiting	Basic Science	Drug Drug Interaction (DDI)	1	somestatus	stop reason	just information to hide
Not Available	Terminated	Supportive Care	Fatigue / Unspecified Adult Solid Tumor, Protocol Specific / Unspecified Childhood Solid Tumor, Protocol Specific	1	somestatus	stop reason	just information to hide
Not Available	Unknown Status	Not Available	Depression	1	somestatus	stop reason	just information to hide
4	Completed	Basic Science	Transplanted Organ Rejection	1	somestatus	stop reason	just information to hide
4	Completed	Basic Science	Type 2 Diabetes Mellitus	1	somestatus	stop reason	just information to hide

Pharmacoeconomics

Manufacturers

Reckitt benckiser

Packagers

Amend
BF Ascher & Co.
Great Southern Laboratories
MCR American Pharmaceuticals Inc.
Medisca Inc.
Novartis AG
Pharmaceutical Association
Prescript Pharmaceuticals
Procter & Gamble
Spectrum Pharmaceuticals
The F. Dohmen Co.
Topco
Wyeth Pharmaceuticals

Dosage Forms

Form	Route	Strength
Capsule	Oral	15 mg/1
Liquid	Oral	30 mg/10mL
Solution	Oral	30 mg/10mL
Capsule, liquid filled	Not applicable
Tablet, effervescent	Oral
Granule, effervescent	Oral
Tablet, multilayer, extended release	Oral
Elixir	Oral	15.75 mg/5ml
Syrup	Oral	30 mg / 5 mL
Lozenge	Oral	30 mg
Liquid	Oral	7.5 mg / unit
Lozenge	Oral	7.5 mg / loz
Lozenge	Oral	7.5 mg
Strip	Oral	15 mg
Syrup	Oral	30 mg / 10 mL
Solution	Oral	7.5 mg / 5 mL
Suspension / drops	Oral
Syrup	Oral	0.200 g
Syrup	Oral	2 MG/ML
Tablet	Transmucosal	10.5 MG
Liquid	Oral
Syrup	Oral	0.15 g
Liquid	Oral	12.5 mg / 5 mL
Solution	Oral	15 mg / 5 mL
Liquid	Topical
Capsule	Oral	250.0000 mg
Lozenge	Oral
Solution	Oral	15 mg/5mL
Solution	Oral
Solution / drops	Oral
Capsule	Oral	15 MG
Kit; tablet, coated	Oral
Syrup	Oral	30 mg
Capsule, gelatin coated	Oral	10.50 mg
Capsule, gelatin coated; kit; tablet	Oral
Solution	Oral	15 mg/15mL
Tablet, sugar coated	Oral
Suspension	Oral	30 mg/5mL
Liquid	Oral	30 mg / 5 mL
Syrup	Oral	20 mg/15mL
Syrup	Oral	5 mg/5mL
Kit; liquid; solution	Oral
Kit; tablet; tablet, coated	Oral
Syrup	Oral	10 mg / 15 mL
Kit; liquid	Oral
Capsule; kit	Oral
Capsule, gelatin coated; capsule, liquid filled; kit	Oral
Syrup	Oral	0.300 g
Tablet, chewable	Oral
Suspension, extended release	Oral	30 mg/5mL
Syrup	Oral	30 mg/5mL
Kit; suspension, extended release	Oral
Tablet	Oral	15 mg/1
Suspension	Oral	30 mg / 5 mL
Tablet, chewable	Oral
Capsule	Oral
Solution	Oral
Tablet, film coated	Oral
Elixir	Oral	5.5 mg/5ml
Tablet, film coated	Oral	15 mg
Pastille	Oral	10.5 MG
Capsule, liquid filled	Oral	15 mg/1
Powder	Not applicable	1 g/1g
Elixir	Oral	15 mg/5ml
Syrup	Oral	0.3 g
Tablet, film coated	Oral
Syrup	Not applicable
Elixir; kit; solution	Oral
Cream; kit; liquid; ointment; tablet; tablet, chewable; tablet, film coated	Oral; Topical
Tablet, chewable	Oral	7.5 mg / tab
Syrup	Oral	7.5 mg / 5 mL
Syrup	Oral	15 mg / 5 mL
Capsule	Oral	10 mg
Liquid	Oral	7.5 mg/5mL
Tablet	Oral	15 mg
Capsule	Oral	30 mg
Tablet, orally disintegrating	Oral	30 mg/1
Syrup	Oral	3 mg/ml
Syrup	Oral	1.5 mg/ml
Kit	Oral
Liquid	Oral	20 mg/5mL
Tablet	Oral	10 mg
Granule	Oral	650.00 mg
Granule	Oral
Kit; powder	Oral
Tablet; tablet, film coated	Oral
Solution / drops	Oral
Syrup	Oral
Solution / drops	Nasal
Capsule, liquid filled	Oral	30 mg
Syrup	Oral	30 mg/1
Syrup	Oral	20 mg/20mL
Tablet	Transmucosal
Elixir	Oral
Strip	Oral	7.5 mg
Tablet		7.5 MG
Tablet, orally disintegrating	Oral
Solution / drops	Oral	15 G
Kit; tablet	Oral
Suppository	Rectal
Syrup	Oral	2 mg/5ml
Kit; solution; suspension	Oral
Tablet, extended release	Oral
Kit; tablet, film coated	Oral
Kit; tablet, coated; tablet, film coated	Oral
Capsule, liquid filled; kit; solution	Nasal; Oral
Syrup	Oral	5 mg/5ml
Tablet	Oral	8 mg
Capsule	Oral
Capsule, liquid filled	Oral
Capsule, gelatin coated	Oral
Solution / drops	Oral	30 MG/ML
Syrup	Oral	30 MG/10ML
Syrup	Oral	300.000 mg
Strip	Oral
Capsule, coated	Oral
Capsule, gelatin coated	Oral	15 mg/1
Tablet	Oral	30.00 mg
Tablet	Oral	30 mg
Syrup	Oral	300 mg
Liquid	Oral	15 mg / 5 mL
Liquid	Oral	7.5 mg / 5 mL
Powder	Oral	10 mg
Syrup	Oral	1 mg/5ml
Tablet	Oral	15 mg
Powder	Oral
Syrup	Oral	0.2 g
Patch	Topical
Tablet	Oral
Granule, for solution	Oral
Solution	Oral	0.1000 g
Tablet	Oral	15.000 mg
Suspension	Oral
Syrup	Oral	0.1330 g
Capsule, liquid filled; kit	Oral
Powder, for solution	Oral
Liquid	Oral	15 mg/5mL
Syrup	Oral	10 mg / 5 mL
Syrup	Oral	10 mg/5mL
Liquid	Oral	30 mg/3mL
Tablet	Oral	30 mg/1
Liquid	Oral	10 mg/5mL
Tablet, coated	Oral
Liquid	Oral	30 mg/5mL
Syrup	Oral
Tablet
Lozenge	Oral	10 mg/1
Lozenge	Oral	15 mg
Lozenge	Oral	10 mg
Syrup	Oral	125 mg/5ml
Liquid	Oral	15 mg/15mL
Kit; solution	Oral
Kit; powder, for solution	Oral
Kit; powder; syrup	Oral
Syrup	Oral	7.5 mg/5mL
Tablet	Oral	7.5 mg
Syrup	Oral	1.500 g
Kit; syrup	Oral
Syrup	Oral	0.113 g
Solution	Oral	2 mg/ml
Tablet	Oral	500.000 mg
Syrup	Oral	133 MG/100ML
Suspension	Oral	1000 mg/1
Kit; suspension	Oral
Liquid	Oral	30 mg/15mL
Liquid	Oral	30 mg / 15 mL
Syrup	Oral	5 mg / 5 mL
Liquid	Oral	30 mg/30mL
Liquid	Oral	15 mg / 15 mL
Syrup	Oral	1.33 MG/ML
Pastille	Oral
Capsule	Oral	10.00 mg
Capsule	Oral	250.000 mg
Spray	Oral	6 mg/0.25mL
Tablet, film coated
Lozenge	Oral	5 mg
Suspension
Syrup	Oral	15 mg/5ml
Tablet		15 mg
Tablet
Tablet, coated	Oral	30 mg
Tablet, coated	Oral	15 mg
Tablet, sugar coated	Oral	15 mg
Syrup
Capsule

Prices

Unit description	Cost	Unit
Modicon (28) 28 0.5-35 mg-mcg tablet Disp Pack	59.99USD	disp
Dextromethorphan powder	14.93USD	g
Dextromethorphan hbr powder	4.74USD	g
Dextromethorphan hbr cryst	2.06USD	g
Triaminic allergy thin strip	0.35USD	strip
Triaminic cold-stuff nose strip	0.35USD	strip
Triaminic cgh-runny nose strip	0.3USD	each
Triaminic cough strips	0.3USD	strip
Triaminic cough-cold chew	0.27USD	each
Triaminic softchew tablet	0.27USD	tablet
Robitussin coughgels	0.25USD	each
Triaminic softchews tablet	0.25USD	tablet
Childrens triaminic decon spray	0.24USD	ml
Hold 4 hour lozenge regular	0.24USD	lozenge
Hca severe cough stopper cplet	0.23USD	each
Triaminicin tablet	0.23USD	tablet
Delsym 30 mg/5 ml suspension	0.11USD	ml
Robitussin dm to go liquid	0.09USD	ml
Apap allergy sinus caplet	0.05USD	caplet
Adlt robitussin cough-cold-flu	0.04USD	ml
Adt robitussin cough-cold d lq	0.04USD	ml
Adult robitussin cough syrup	0.04USD	ml
Robitussin chest congest syrup	0.04USD	ml
Robitussin cough & cold liquid	0.04USD	ml
Robitussin cough-cold liquid	0.04USD	ml
Robitussin cough-cong syrup	0.04USD	ml
Robitussin dm max liquid	0.04USD	ml
Robitussin long-acting liq	0.04USD	ml
Robitussin pe head & chest liq	0.04USD	ml
Robitussin-cough-chest-cong lq	0.04USD	ml
Robitussin-dm cough syrup	0.04USD	ml
Triaminic chest-nasal cong liq	0.04USD	ml
Triaminic cold & cough liquid	0.04USD	ml
Triaminic cold-allergy pe liq	0.04USD	ml
Triaminic cough-nasal cong liq	0.04USD	ml
Triaminic cough-sore throat lq	0.04USD	ml
Triaminic flu cough-fever susp	0.04USD	ml
Triaminic flu-cough-fever liq	0.04USD	ml
Triaminic-d syrup	0.04USD	ml
Vicks 44 cough liquid	0.03USD	ml
Vicks 44 custom care liquid	0.03USD	ml
Guaifenesin dm syrup	0.02USD	ml

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
US5980882	No	1999-11-09	2017-04-16
US6372252	No	2002-04-16	2020-04-28
US6955821	No	2005-10-18	2020-04-28
US7838032	No	2010-11-23	2020-04-28
US7659282	No	2010-02-09	2026-08-13
US8227484	No	2012-07-24	2023-07-17
USRE38115	No	2003-05-06	2016-01-26
US11382874	No	2014-11-05	2034-11-05
US11364233	No	2014-11-05	2034-11-05
US9457025	No	2016-10-04	2034-11-05
US10058518	No	2018-08-28	2034-11-05
US9278095	No	2016-03-08	2034-11-05
US9867819	No	2018-01-16	2034-11-05
US9168234	No	2015-10-27	2034-11-05
US9861595	No	2018-01-09	2034-11-05
US8569328	No	2013-10-29	2033-10-29
US9700553	No	2017-07-11	2034-11-05
US11357744	No	2014-11-05	2034-11-05
US11344544	No	2014-11-05	2034-11-05
US9486450	No	2016-11-08	2034-11-05
US9474731	No	2016-10-25	2034-11-05
US9375429	No	2016-06-28	2034-11-05
US9421176	No	2016-08-23	2034-11-05
US9408815	No	2016-08-09	2034-11-05
US9763932	No	2017-09-19	2034-11-05
US11311534	No	2014-11-05	2034-11-05
US9205083	No	2015-12-08	2034-11-05
US9707191	No	2017-07-18	2034-11-05
US10898453	No	2021-01-26	2034-11-05
US11433067	No	2014-11-05	2034-11-05
US9700528	No	2017-07-11	2034-11-05
US9370513	No	2016-06-21	2034-11-05
US9457023	No	2016-10-04	2034-11-05
US9238032	No	2016-01-19	2034-11-05
US11096937	No	2021-08-24	2034-11-05
US11298352	No	2014-11-05	2034-11-05
US10966941	No	2021-04-06	2034-11-05
US11298351	No	2014-11-05	2034-11-05
US11090300	No	2021-08-17	2034-11-05
US10894047	No	2021-01-19	2034-11-05
US10064857	No	2018-09-04	2034-11-05
US11291665	No	2014-11-05	2034-11-05
US10780066	No	2020-09-22	2034-11-09
US10780064	No	2020-09-22	2040-01-07
US11291638	No	2014-11-05	2034-11-05
US10786469	No	2020-09-29	2034-11-05
US11253492	No	2014-11-05	2034-11-05
US10881657	No	2021-01-05	2034-11-05
US10874663	No	2020-12-29	2034-11-05
US10799497	No	2020-10-13	2034-11-05
US11058648	No	2021-07-13	2034-11-05
US11273133	No	2014-11-05	2034-11-05
US10864209	No	2020-12-15	2034-11-05
US10806710	No	2020-10-20	2034-11-05
US10881624	No	2021-01-05	2034-11-05
US10786496	No	2020-09-29	2034-11-05
US11020389	No	2021-06-01	2034-11-05
US11185515	No	2021-11-30	2034-11-05
US10945973	No	2021-03-16	2034-11-05
US10966942	No	2021-04-06	2040-01-07
US11285146	No	2014-11-05	2034-11-05
US11285118	No	2014-11-05	2034-11-05
US10596167	No	2020-03-24	2034-11-05
US11439636	No	2014-11-05	2034-11-05
US9314462	No	2016-04-19	2034-11-05
US9198905	No	2015-12-01	2034-11-05
US11426401	No	2014-11-05	2034-11-05
US11426370	No	2014-11-05	2034-11-05
US11419867	No	2014-11-05	2034-11-05
US10772850	No	2020-09-15	2034-11-05
US10940124	No	2021-03-09	2040-01-07
US11273134	No	2014-11-05	2034-11-05
US11253491	No	2014-11-05	2034-11-05
US11234946	No	2014-11-05	2034-11-05
US10548857	No	2020-02-04	2034-11-05
US11229640	No	2014-11-05	2034-11-05
US10874665	No	2020-12-29	2034-11-05
US10933034	No	2021-03-02	2034-11-05
US10251879	No	2019-04-09	2034-11-05
US10925842	No	2021-02-23	2040-01-07
US10092561	No	2018-10-09	2034-11-05
US10894046	No	2021-01-19	2034-11-05
US11191739	No	2021-12-07	2034-11-05
US10874664	No	2020-12-29	2034-11-05
US10080727	No	2018-09-25	2034-11-05
US11197839	No	2021-12-14	2034-11-05
US11147808	No	2021-10-19	2034-11-05
US11207281	No	2021-12-28	2034-11-05
US11141416	No	2021-10-12	2034-11-05
US11141388	No	2021-10-12	2034-11-05
US11213521	No	2014-11-05	2034-11-05
US11129826	No	2021-09-28	2034-11-05
US11123343	No	2021-09-21	2034-11-05
US10966974	No	2021-04-06	2034-11-05
US10512643	No	2019-12-24	2034-11-05
US10463634	No	2019-11-05	2034-11-05
US10105361	No	2018-10-23	2034-11-05
US10105327	No	2018-10-23	2034-11-05
US10092560	No	2018-10-09	2034-11-05
US9968568	No	2018-05-15	2034-11-05
US11510918	No	2014-11-05	2034-11-05
US11478468	No	2014-11-05	2034-11-05
US11497721	No	2014-11-05	2034-11-05
US11524008	No	2014-11-05	2034-11-05
US11524007	No	2014-11-05	2034-11-05
US11517542	No	2014-11-05	2034-11-05
US11517543	No	2014-11-05	2034-11-05
US11541048	No	2014-11-05	2034-11-05
US11541021	No	2014-11-05	2034-11-05
US11534414	No	2014-11-05	2034-11-05
US11596627	No	2014-11-05	2034-11-05
US11617728	No	2014-11-05	2034-11-05
US11617747	No	2014-11-05	2034-11-05
US11730706	No	2023-01-23	2043-01-23
US11717518	No	2023-01-20	2043-01-20
US11752144	No	2023-02-23	2043-02-23
US11779579	No	2014-11-05	2034-11-05
US11844797	No	2023-04-20	2043-04-20
US11839612	No	2023-03-02	2043-03-02
US11896563	No	2021-12-01	2041-12-01
US11883373	No	2023-01-23	2043-01-23
US11925636	No	2023-01-20	2043-01-20
US11969421	No	2014-11-05	2034-11-05
US11986444	No	2023-02-15	2043-02-15
US12042473	No	2023-02-23	2043-02-23
US12036191	No	2023-02-15	2043-02-15

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	122-124	Schnider, O. and Grussner, A,; US. Patent 2,676,177; April 20, 1954; assigned to Hoffrnann-La Roche Inc.
water solubility	25g/100mL	FDA Drug Quality Assessment: Nudexta Dextromethorphan and Quinidine Capsules

Predicted Properties

Property	Value	Source
Water Solubility	0.00851 mg/mL	ALOGPS
logP	3.75	ALOGPS
logP	3.49	Chemaxon
logS	-4.5	ALOGPS
pKa (Strongest Basic)	9.85	Chemaxon
Physiological Charge	1	Chemaxon
Hydrogen Acceptor Count	2	Chemaxon
Hydrogen Donor Count	0	Chemaxon
Polar Surface Area	12.47 Å²	Chemaxon
Rotatable Bond Count	1	Chemaxon
Refractivity	82.56 m³·mol^-1	Chemaxon
Polarizability	31.86 Å³	Chemaxon
Number of Rings	4	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	Yes	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.9959
Blood Brain Barrier	+	0.9989
Caco-2 permeable	+	0.8867
P-glycoprotein substrate	Substrate	0.8288
P-glycoprotein inhibitor I	Inhibitor	0.654
P-glycoprotein inhibitor II	Non-inhibitor	0.8383
Renal organic cation transporter	Inhibitor	0.7893
CYP450 2C9 substrate	Non-substrate	0.8187
CYP450 2D6 substrate	Substrate	0.8919
CYP450 3A4 substrate	Substrate	0.7783
CYP450 1A2 substrate	Non-inhibitor	0.9046
CYP450 2C9 inhibitor	Non-inhibitor	0.9071
CYP450 2D6 inhibitor	Inhibitor	0.8932
CYP450 2C19 inhibitor	Non-inhibitor	0.9025
CYP450 3A4 inhibitor	Non-inhibitor	0.8308
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.8673
Ames test	Non AMES toxic	0.5664
Carcinogenicity	Non-carcinogens	0.9616
Biodegradation	Not ready biodegradable	0.9763
Rat acute toxicity	3.3377 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.7107
hERG inhibition (predictor II)	Inhibitor	0.6723

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Mass Spectrum (Electron Ionization)	MS	splash10-00di-5890000000-3009baa7e8a19f9be270
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-014i-0190000000-df99af2429c385c2ac44
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-00di-0090000000-1a3ed289b3e93cd6fde4
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-00di-0090000000-ebc22884ca50d755e2e4
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-00di-0090000000-63612671cfd5e7808f7e
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-02mi-0490000000-10cc5d461942becb6194
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-022a-0930000000-943342d8d5a3ae45227f
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-00di-0900000000-eb4c5442e33e6921c728
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-00di-0090000000-a39a4c295bd6e3b25181
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-00di-0090000000-5191ea197708a687222f
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-00di-0090000000-3d90a3bd5c1b6788ed43
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-02mi-0490000000-ddc598f28e1a4f9008d1
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-022a-0940000000-cbb4007ab43d33441b69
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-00dj-0900000000-457827e6b58fa1a77623
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-014i-0190000000-23c81d81c3ea162f7ab7
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-00di-0090000000-1be40c3a6e8dc1309d3d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-00di-0090000000-5b655dbdd7f0dfb89568
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-00dr-0090000000-843d9ad8469fbcc4b08c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-02tc-2390000000-28393a7b0dcef2929abe
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-00di-0090000000-b936a4ab9c28636b57ae
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0ita-0290000000-8993598797c0e153c378
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	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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Details1. Sigma non-opioid intracellular receptor 1

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Agonist

General 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 membrane. Involved in the regulation of different receptors it plays a role in BDNF signaling and EGF signaling. Also regulates ion channels like the potassium channel and could modulate neurotransmitter release. Plays a role in calcium signaling through modulation together with ANK2 of the ITP3R-dependent calcium efflux at the endoplasmic reticulum. Plays a role in several other cell functions including proliferation, survival and death. Originally identified for its ability to bind various psychoactive drugs it is involved in learning processes, memory and mood alteration (PubMed:16472803, PubMed:9341151). Necessary for proper mitochondrial axonal transport in motor neurons, in particular the retrograde movement of mitochondria. Plays a role in protecting cells against oxidative stress-induced cell death via its interaction with RNF112 (By similarity)
Specific Function: G protein-coupled opioid receptor activity
Gene Name: SIGMAR1
Uniprot ID: Q99720
Uniprot Name: Sigma non-opioid intracellular receptor 1
Molecular Weight: 25127.52 Da

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
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]
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]
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]
Church AJ, Andrew RD: Spreading depression expands traumatic injury in neocortical brain slices. J Neurotrauma. 2005 Feb;22(2):277-90. [Article]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
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]
Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]

Details2. Aromatase

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Inhibitor

General Function: A cytochrome P450 monooxygenase that catalyzes the conversion of C19 androgens, androst-4-ene-3,17-dione (androstenedione) and testosterone to the C18 estrogens, estrone and estradiol, respectively (PubMed:27702664, PubMed:2848247). Catalyzes three successive oxidations of C19 androgens: two conventional oxidations at C19 yielding 19-hydroxy and 19-oxo/19-aldehyde derivatives, followed by a third oxidative aromatization step that involves C1-beta hydrogen abstraction combined with cleavage of the C10-C19 bond to yield a phenolic A ring and formic acid (PubMed:20385561). Alternatively, the third oxidative reaction yields a 19-norsteroid and formic acid. Converts dihydrotestosterone to delta1,10-dehydro 19-nordihydrotestosterone and may play a role in homeostasis of this potent androgen (PubMed:22773874). Also displays 2-hydroxylase activity toward estrone (PubMed:22773874). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (CPR; NADPH-ferrihemoprotein reductase) (PubMed:20385561, PubMed:22773874)
Specific Function: Aromatase activity
Gene Name: CYP19A1
Uniprot ID: P11511
Uniprot Name: Aromatase
Molecular Weight: 57882.48 Da

References

Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]

Details3. Glutamate receptor ionotropic, NMDA 3A

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Antagonist

General 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. During the development of neural circuits, plays a role in the synaptic refinement period, restricting spine maturation and growth. By competing with GIT1 interaction with ARHGEF7/beta-PIX, may reduce GIT1/ARHGEF7-regulated local activation of RAC1, hence affecting signaling and limiting the maturation and growth of inactive synapses. May also play a role in PPP2CB-NMDAR mediated signaling mechanism
Specific Function: Calcium channel activity
Gene Name: GRIN3A
Uniprot ID: Q8TCU5
Uniprot Name: Glutamate receptor ionotropic, NMDA 3A
Molecular Weight: 125464.07 Da

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
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]
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]
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]
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]

Details4. Neuronal acetylcholine receptor subunit alpha-2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Antagonist

General 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
Specific Function: Acetylcholine receptor activity
Gene Name: CHRNA2
Uniprot ID: Q15822
Uniprot Name: Neuronal acetylcholine receptor subunit alpha-2
Molecular Weight: 59764.82 Da

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
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]
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]
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]

Details5. Sodium-dependent serotonin transporter

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Serotonin transporter that cotransports serotonin with one Na(+) ion in exchange for one K(+) ion and possibly one proton in an overall electroneutral transport cycle. Transports serotonin across the plasma membrane from the extracellular compartment to the cytosol thus limiting serotonin intercellular signaling (PubMed:10407194, PubMed:12869649, PubMed:21730057, PubMed:27049939, PubMed:27756841, PubMed:34851672). Essential for serotonin homeostasis in the central nervous system. In the developing somatosensory cortex, acts in glutamatergic neurons to control serotonin uptake and its trophic functions accounting for proper spatial organization of cortical neurons and elaboration of sensory circuits. In the mature cortex, acts primarily in brainstem raphe neurons to mediate serotonin uptake from the synaptic cleft back into the pre-synaptic terminal thus terminating serotonin signaling at the synapse (By similarity). Modulates mucosal serotonin levels in the gastrointestinal tract through uptake and clearance of serotonin in enterocytes. Required for enteric neurogenesis and gastrointestinal reflexes (By similarity). Regulates blood serotonin levels by ensuring rapid high affinity uptake of serotonin from plasma to platelets, where it is further stored in dense granules via vesicular monoamine transporters and then released upon stimulation (PubMed:17506858, PubMed:18317590). Mechanistically, the transport cycle starts with an outward-open conformation having Na1(+) and Cl(-) sites occupied. The binding of a second extracellular Na2(+) ion and serotonin substrate leads to structural changes to outward-occluded to inward-occluded to inward-open, where the Na2(+) ion and serotonin are released into the cytosol. Binding of intracellular K(+) ion induces conformational transitions to inward-occluded to outward-open and completes the cycle by releasing K(+) possibly together with a proton bound to Asp-98 into the extracellular compartment. Na1(+) and Cl(-) ions remain bound throughout the transport cycle (PubMed:10407194, PubMed:12869649, PubMed:21730057, PubMed:27049939, PubMed:27756841, PubMed:34851672). Additionally, displays serotonin-induced channel-like conductance for monovalent cations, mainly Na(+) ions. The channel activity is uncoupled from the transport cycle and may contribute to the membrane resting potential or excitability (By similarity)
Specific Function: Actin filament binding
Gene Name: SLC6A4
Uniprot ID: P31645
Uniprot Name: Sodium-dependent serotonin transporter
Molecular Weight: 70324.165 Da

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
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]
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]
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]

Details6. Membrane-associated progesterone receptor component 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Binder

General Function: Component of a progesterone-binding protein complex (PubMed:28396637). Binds progesterone (PubMed:25675345). Has many reported cellular functions (heme homeostasis, interaction with CYPs). Required for the maintenance of uterine histoarchitecture and normal female reproductive lifespan (By similarity). Intracellular heme chaperone. Regulates heme synthesis via interactions with FECH and acts as a heme donor for at least some hemoproteins (PubMed:27599036). Forms a ternary complex with TMEM97 receptor and low density lipid receptor/LDLR, which increases LDLR-mediated LDL lipoprotein internalization (PubMed:30443021)
Specific Function: Amyloid-beta binding
Gene Name: PGRMC1
Uniprot ID: O00264
Uniprot Name: Membrane-associated progesterone receptor component 1
Molecular Weight: 21670.9 Da

References

Chou YC, Liao JF, Chang WY, Lin MF, Chen CF: Binding of dimemorfan to sigma-1 receptor and its anticonvulsant and locomotor effects in mice, compared with dextromethorphan and dextrorphan. Brain Res. 1999 Mar 13;821(2):516-9. [Article]

Details7. Neuronal acetylcholine receptor subunit alpha-3

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Antagonist

General 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
Specific Function: Acetylcholine binding
Gene Name: CHRNA3
Uniprot ID: P32297
Uniprot Name: Neuronal acetylcholine receptor subunit alpha-3
Molecular Weight: 57479.54 Da

References

Damaj MI, Flood P, Ho KK, May EL, Martin BR: Effect of dextrometorphan and dextrorphan on nicotine and neuronal nicotinic receptors: in vitro and in vivo selectivity. J Pharmacol Exp Ther. 2005 Feb;312(2):780-5. Epub 2004 Sep 8. [Article]

Details8. Neuronal acetylcholine receptor subunit alpha-4

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Antagonist

General 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 permeable to sodium ions
Specific Function: Acetylcholine binding
Gene Name: CHRNA4
Uniprot ID: P43681
Uniprot Name: Neuronal acetylcholine receptor subunit alpha-4
Molecular Weight: 69956.47 Da

References

Damaj MI, Flood P, Ho KK, May EL, Martin BR: Effect of dextrometorphan and dextrorphan on nicotine and neuronal nicotinic receptors: in vitro and in vivo selectivity. J Pharmacol Exp Ther. 2005 Feb;312(2):780-5. Epub 2004 Sep 8. [Article]

Details9. Neuronal acetylcholine receptor subunit beta-4

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Antagonist

General 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
Specific Function: Acetylcholine receptor activity
Gene Name: CHRNB4
Uniprot ID: P30926
Uniprot Name: Neuronal acetylcholine receptor subunit beta-4
Molecular Weight: 56378.985 Da

References

Damaj MI, Flood P, Ho KK, May EL, Martin BR: Effect of dextrometorphan and dextrorphan on nicotine and neuronal nicotinic receptors: in vitro and in vivo selectivity. J Pharmacol Exp Ther. 2005 Feb;312(2):780-5. Epub 2004 Sep 8. [Article]

Details10. Neuronal acetylcholine receptor subunit beta-2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Antagonist

General 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 permeable to sodiun ions
Specific Function: Acetylcholine binding
Gene Name: CHRNB2
Uniprot ID: P17787
Uniprot Name: Neuronal acetylcholine receptor subunit beta-2
Molecular Weight: 57018.575 Da

References

Damaj MI, Flood P, Ho KK, May EL, Martin BR: Effect of dextrometorphan and dextrorphan on nicotine and neuronal nicotinic receptors: in vitro and in vivo selectivity. J Pharmacol Exp Ther. 2005 Feb;312(2):780-5. Epub 2004 Sep 8. [Article]

Details11. Neuronal acetylcholine receptor subunit alpha-7

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Antagonist

General 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 channel is blocked by alpha-bungarotoxin
Specific Function: Acetylcholine binding
Gene Name: CHRNA7
Uniprot ID: P36544
Uniprot Name: Neuronal acetylcholine receptor subunit alpha-7
Molecular Weight: 56448.925 Da

References

Damaj MI, Flood P, Ho KK, May EL, Martin BR: Effect of dextrometorphan and dextrorphan on nicotine and neuronal nicotinic receptors: in vitro and in vivo selectivity. J Pharmacol Exp Ther. 2005 Feb;312(2):780-5. Epub 2004 Sep 8. [Article]

Details12. Mu-type opioid receptor

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Agonist
Regulator

General Function: Receptor for endogenous opioids such as beta-endorphin and endomorphin (PubMed:10529478, PubMed:12589820, PubMed:7891175, PubMed:7905839, PubMed:7957926, PubMed:9689128). Receptor for natural and synthetic opioids including morphine, heroin, DAMGO, fentanyl, etorphine, buprenorphin and methadone (PubMed:10529478, PubMed:10836142, PubMed:12589820, PubMed:19300905, PubMed:7891175, PubMed:7905839, PubMed:7957926, PubMed:9689128). Also activated by enkephalin peptides, such as Met-enkephalin or Met-enkephalin-Arg-Phe, with higher affinity for Met-enkephalin-Arg-Phe (By similarity). Agonist binding to the receptor induces coupling to an inactive GDP-bound heterotrimeric G-protein complex and subsequent exchange of GDP for GTP in the G-protein alpha subunit leading to dissociation of the G-protein complex with the free GTP-bound G-protein alpha and the G-protein beta-gamma dimer activating downstream cellular effectors (PubMed:7905839). The agonist- and cell type-specific activity is predominantly coupled to pertussis toxin-sensitive G(i) and G(o) G alpha proteins, GNAI1, GNAI2, GNAI3 and GNAO1 isoforms Alpha-1 and Alpha-2, and to a lesser extent to pertussis toxin-insensitive G alpha proteins GNAZ and GNA15 (PubMed:12068084). They mediate an array of downstream cellular responses, including inhibition of adenylate cyclase activity and both N-type and L-type calcium channels, activation of inward rectifying potassium channels, mitogen-activated protein kinase (MAPK), phospholipase C (PLC), phosphoinositide/protein kinase (PKC), phosphoinositide 3-kinase (PI3K) and regulation of NF-kappa-B (By similarity). Also couples to adenylate cyclase stimulatory G alpha proteins (By similarity). The selective temporal coupling to G-proteins and subsequent signaling can be regulated by RGSZ proteins, such as RGS9, RGS17 and RGS4 (By similarity). Phosphorylation by members of the GPRK subfamily of Ser/Thr protein kinases and association with beta-arrestins is involved in short-term receptor desensitization (By similarity). Beta-arrestins associate with the GPRK-phosphorylated receptor and uncouple it from the G-protein thus terminating signal transduction (By similarity). The phosphorylated receptor is internalized through endocytosis via clathrin-coated pits which involves beta-arrestins (By similarity). The activation of the ERK pathway occurs either in a G-protein-dependent or a beta-arrestin-dependent manner and is regulated by agonist-specific receptor phosphorylation (By similarity). Acts as a class A G-protein coupled receptor (GPCR) which dissociates from beta-arrestin at or near the plasma membrane and undergoes rapid recycling (By similarity). Receptor down-regulation pathways are varying with the agonist and occur dependent or independent of G-protein coupling (By similarity). Endogenous ligands induce rapid desensitization, endocytosis and recycling (By similarity). Heterooligomerization with other GPCRs can modulate agonist binding, signaling and trafficking properties (By similarity)
Specific Function: Beta-endorphin receptor activity
Gene Name: OPRM1
Uniprot ID: P35372
Uniprot Name: Mu-type opioid receptor
Molecular Weight: 44778.855 Da

References

Codd EE, Shank RP, Schupsky JJ, Raffa RB: Serotonin and norepinephrine uptake inhibiting activity of centrally acting analgesics: structural determinants and role in antinociception. J Pharmacol Exp Ther. 1995 Sep;274(3):1263-70. [Article]
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]

Details13. Delta-type opioid receptor

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Agonist

General Function: G-protein coupled receptor that functions as a receptor for endogenous enkephalins and for a subset of other opioids. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Signaling leads to the inhibition of adenylate cyclase activity. Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Plays a role in the perception of pain and in opiate-mediated analgesia. Plays a role in developing analgesic tolerance to morphine
Specific Function: G protein-coupled enkephalin receptor activity
Gene Name: OPRD1
Uniprot ID: P41143
Uniprot Name: Delta-type opioid receptor
Molecular Weight: 40368.235 Da

References

Codd EE, Shank RP, Schupsky JJ, Raffa RB: Serotonin and norepinephrine uptake inhibiting activity of centrally acting analgesics: structural determinants and role in antinociception. J Pharmacol Exp Ther. 1995 Sep;274(3):1263-70. [Article]

Details14. Kappa-type opioid receptor

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Agonist

General Function: G-protein coupled opioid receptor that functions as a receptor for endogenous alpha-neoendorphins and dynorphins, but has low affinity for beta-endorphins. Also functions as a receptor for various synthetic opioids and for the psychoactive diterpene salvinorin A. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Signaling leads to the inhibition of adenylate cyclase activity. Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Plays a role in the perception of pain. Plays a role in mediating reduced physical activity upon treatment with synthetic opioids. Plays a role in the regulation of salivation in response to synthetic opioids. May play a role in arousal and regulation of autonomic and neuroendocrine functions
Specific Function: Dynorphin receptor activity
Gene Name: OPRK1
Uniprot ID: P41145
Uniprot Name: Kappa-type opioid receptor
Molecular Weight: 42644.665 Da

References

Codd EE, Shank RP, Schupsky JJ, Raffa RB: Serotonin and norepinephrine uptake inhibiting activity of centrally acting analgesics: structural determinants and role in antinociception. J Pharmacol Exp Ther. 1995 Sep;274(3):1263-70. [Article]

Details15. NADPH oxidase (Protein Group)

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: 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 across the plasma membrane to molecular oxygen on the exterior. Also functions as a voltage-gated proton channel that mediates the H(+) currents of resting phagocytes. It participates in the regulation of cellular pH and is blocked by zinc
Specific Function: Flavin adenine dinucleotide binding

Components:

Name	UniProt ID
Cytochrome b-245 heavy chain	P04839
Cytochrome b-245 light chain	P13498
Neutrophil cytosol factor 1	P14598
Neutrophil cytosol factor 2	P19878
Neutrophil cytosol factor 4	Q15080
Ras-related C3 botulinum toxin substrate 1	P63000
Ras-related C3 botulinum toxin substrate 2	P15153

References

Zhang W, Wang T, Qin L, Gao HM, Wilson B, Ali SF, Zhang W, Hong JS, Liu B: Neuroprotective effect of dextromethorphan in the MPTP Parkinson's disease model: role of NADPH oxidase. FASEB J. 2004 Mar;18(3):589-91. Epub 2004 Jan 20. [Article]
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]

Details16. Sodium-dependent noradrenaline transporter

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Mediates sodium- and chloride-dependent transport of norepinephrine (also known as noradrenaline) (PubMed:2008212, PubMed:8125921). Can also mediate sodium- and chloride-dependent transport of dopamine (PubMed:11093780, PubMed:8125921)
Specific Function: Actin binding
Gene Name: SLC6A2
Uniprot ID: P23975
Uniprot Name: Sodium-dependent noradrenaline transporter
Molecular Weight: 69331.42 Da

References

Codd EE, Shank RP, Schupsky JJ, Raffa RB: Serotonin and norepinephrine uptake inhibiting activity of centrally acting analgesics: structural determinants and role in antinociception. J Pharmacol Exp Ther. 1995 Sep;274(3):1263-70. [Article]

Enzymes

Details1. Cytochrome P450 2D6

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: A cytochrome P450 monooxygenase involved in the metabolism of fatty acids, steroids and retinoids (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:19965576, PubMed:20972997). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 20-hydroxyeicosatetraenoic acid ethanolamide (20-HETE-EA) and 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:18698000, PubMed:21289075). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Catalyzes the oxidative transformations of all-trans retinol to all-trans retinal, a precursor for the active form all-trans-retinoic acid (PubMed:10681376). Also involved in the oxidative metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants
Specific Function: Anandamide 11,12 epoxidase activity
Gene Name: CYP2D6
Uniprot ID: P10635
Uniprot Name: Cytochrome P450 2D6
Molecular Weight: 55768.94 Da

References

Zhou SF: Polymorphism of human cytochrome P450 2D6 and its clinical significance: Part I. Clin Pharmacokinet. 2009;48(11):689-723. doi: 10.2165/11318030-000000000-00000. [Article]
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]
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]
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]
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]
Flockhart Table of Drug Interactions [Link]
Source [Link]
FDA Approved Drug Products: Nuedexta Dextromethorphan Hydrobromide and Quinidine Sulfate Oral Capsules [Link]

Details2. Cytochrome P450 3A4

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
Specific Function: 1,8-cineole 2-exo-monooxygenase activity
Gene Name: CYP3A4
Uniprot ID: P08684
Uniprot Name: Cytochrome P450 3A4
Molecular Weight: 57342.67 Da

References

Yu A, Haining RL: Comparative contribution to dextromethorphan metabolism by cytochrome P450 isoforms in vitro: can dextromethorphan be used as a dual probe for both CTP2D6 and CYP3A activities? Drug Metab Dispos. 2001 Nov;29(11):1514-20. [Article]
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]
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]
Flockhart Table of Drug Interactions [Link]

Details3. Cytochrome P450 3A7

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: A cytochrome P450 monooxygenase involved in the metabolism of steroid hormones and vitamins during embryogenesis (PubMed:11093772, PubMed:12865317, PubMed:14559847, PubMed:17178770, PubMed:9555064). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:11093772, PubMed:12865317, PubMed:14559847, PubMed:17178770, PubMed:9555064). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes 3beta-hydroxyandrost-5-en-17-one (dehydroepiandrosterone, DHEA), a precursor in the biosynthesis of androgen and estrogen steroid hormones (PubMed:17178770, PubMed:9555064). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1), particularly D-ring hydroxylated estrone at the C16-alpha position (PubMed:12865317, PubMed:14559847). Mainly hydroxylates all trans-retinoic acid (atRA) to 4-hydroxyretinoate and may play a role in atRA clearance during fetal development (PubMed:11093772). Also involved in the oxidative metabolism of xenobiotics including anticonvulsants (PubMed:9555064)
Specific Function: All-trans retinoic acid 18-hydroxylase activity
Gene Name: CYP3A7
Uniprot ID: P24462
Uniprot Name: Cytochrome P450 3A7
Molecular Weight: 57469.95 Da

References

Gorski JC, Jones DR, Wrighton SA, Hall SD: Characterization of dextromethorphan N-demethylation by human liver microsomes. Contribution of the cytochrome P450 3A (CYP3A) subfamily. Biochem Pharmacol. 1994 Jul 5;48(1):173-82. doi: 10.1016/0006-2952(94)90237-2. [Article]
Flockhart Table of Drug Interactions [Link]

Details4. Cytochrome P450 2B6

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: A cytochrome P450 monooxygenase involved in the metabolism of endocannabinoids and steroids (PubMed:12865317, PubMed:21289075). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the epoxidation of double bonds of arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:21289075). Hydroxylates steroid hormones, including testosterone at C-16 and estrogens at C-2 (PubMed:12865317, PubMed:21289075). Plays a role in the oxidative metabolism of xenobiotics, including plant lipids and drugs (PubMed:11695850, PubMed:22909231). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850)
Specific Function: Anandamide 11,12 epoxidase activity
Gene Name: CYP2B6
Uniprot ID: P20813
Uniprot Name: Cytochrome P450 2B6
Molecular Weight: 56277.81 Da

References

Yu A, Haining RL: Comparative contribution to dextromethorphan metabolism by cytochrome P450 isoforms in vitro: can dextromethorphan be used as a dual probe for both CTP2D6 and CYP3A activities? Drug Metab Dispos. 2001 Nov;29(11):1514-20. [Article]
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]

Details5. Cytochrome P450 2C19

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: A cytochrome P450 monooxygenase involved in the metabolism of polyunsaturated fatty acids (PUFA) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Catalyzes the hydroxylation of carbon-hydrogen bonds. Hydroxylates PUFA specifically at the omega-1 position (PubMed:18577768). Catalyzes the epoxidation of double bonds of PUFA (PubMed:19965576, PubMed:20972997). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). 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 imipramine. Hydroxylates fenbendazole at the 4' position (PubMed:23959307)
Specific Function: (r)-limonene 6-monooxygenase activity
Gene Name: CYP2C19
Uniprot ID: P33261
Uniprot Name: Cytochrome P450 2C19
Molecular Weight: 55944.565 Da

References

von Moltke LL, Greenblatt DJ, Grassi JM, Granda BW, Venkatakrishnan K, Schmider J, Harmatz JS, Shader RI: Multiple human cytochromes contribute to biotransformation of dextromethorphan in-vitro: role of CYP2C9, CYP2C19, CYP2D6, and CYP3A. J Pharm Pharmacol. 1998 Sep;50(9):997-1004. doi: 10.1111/j.2042-7158.1998.tb06914.x. [Article]

Details6. Cytochrome P450 2C9

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids and steroids (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:15766564, PubMed:19965576, PubMed:7574697, PubMed:9866708). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Exhibits low catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes bisallylic hydroxylation and hydroxylation with double-bond migration of polyunsaturated fatty acids (PUFA) (PubMed:9435160, PubMed:9866708). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan (PubMed:25994031)
Specific Function: (r)-limonene 6-monooxygenase activity
Gene Name: CYP2C9
Uniprot ID: P11712
Uniprot Name: Cytochrome P450 2C9
Molecular Weight: 55627.365 Da

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
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]
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]

Details7. UDP-glucuronosyltransferase 2B4

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: UDP-glucuronosyltransferase (UGT) that catalyzes phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase the metabolite's water solubility, thereby facilitating excretion into either the urine or bile (PubMed:18719240, PubMed:23288867). Essential for the elimination and detoxification of drugs, xenobiotics and endogenous compounds (PubMed:18719240, PubMed:23288867). Catalyzes the glucuronidation of the endogenous estrogen hormones such as estradiol and estriol (PubMed:18719240, PubMed:23288867)
Specific Function: Glucuronosyltransferase activity
Gene Name: UGT2B4
Uniprot ID: P06133
Uniprot Name: UDP-glucuronosyltransferase 2B4
Molecular Weight: 60512.035 Da

References

Lutz JD, Isoherranen N: Prediction of relative in vivo metabolite exposure from in vitro data using two model drugs: dextromethorphan and omeprazole. Drug Metab Dispos. 2012 Jan;40(1):159-68. doi: 10.1124/dmd.111.042200. Epub 2011 Oct 18. [Article]

Details8. UDP-glucuronosyltransferase 2B7

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: UDP-glucuronosyltransferase (UGT) that catalyzes phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase the metabolite's water solubility, thereby facilitating excretion into either the urine or bile (PubMed:10702251, PubMed:15470161, PubMed:15472229, PubMed:17442341, PubMed:18674515, PubMed:18719240, PubMed:19022937, PubMed:23288867, PubMed:23756265, PubMed:26220143). Essential for the elimination and detoxification of drugs, xenobiotics and endogenous compounds (PubMed:15470161, PubMed:18674515, PubMed:23756265). Catalyzes the glucuronidation of endogenous steroid hormones such as androgens (epitestosterone, androsterone) and estrogens (estradiol, epiestradiol, estriol, catechol estrogens) (PubMed:15472229, PubMed:17442341, PubMed:18719240, PubMed:19022937, PubMed:2159463, PubMed:23288867, PubMed:26220143). Also regulates the levels of retinoic acid, a major metabolite of vitamin A involved in apoptosis, cellular growth and differentiation, and embryonic development (PubMed:10702251). Contributes to bile acid (BA) detoxification by catalyzing the glucuronidation of BA substrates, which are natural detergents for dietary lipids absorption (PubMed:23756265). Involved in the glucuronidation of the AGTR1 angiotensin receptor antagonist losartan, caderastan and zolarsatan, drugs which can inhibit the effect of angiotensin II (PubMed:18674515). Also metabolizes mycophenolate, an immunosuppressive agent (PubMed:15470161)
Specific Function: Glucuronosyltransferase activity
Gene Name: UGT2B7
Uniprot ID: P16662
Uniprot Name: UDP-glucuronosyltransferase 2B7
Molecular Weight: 60720.15 Da

References

Lutz JD, Isoherranen N: Prediction of relative in vivo metabolite exposure from in vitro data using two model drugs: dextromethorphan and omeprazole. Drug Metab Dispos. 2012 Jan;40(1):159-68. doi: 10.1124/dmd.111.042200. Epub 2011 Oct 18. [Article]

Details9. UDP-glucuronosyltransferase 2B15

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: UDP-glucuronosyltransferase (UGT) that catalyzes phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase the metabolite's water solubility, thereby facilitating excretion into either the urine or bile (PubMed:16595710, PubMed:18719240, PubMed:23288867, PubMed:7835232, PubMed:9295060). Essential for the elimination and detoxification of drugs, xenobiotics and endogenous compounds (PubMed:7835232). Catalyzes the glucuronidation of endogenous steroid hormones such as androgens (testosterone, androsterone) and estrogens (estradiol, epiestradiol, estriol, catechol estrogens) (PubMed:16595710, PubMed:18719240, PubMed:23288867, PubMed:7835232, PubMed:9295060). Displays glucuronidation activity toward several classes of xenobiotic substrates, including phenolic compounds (eugenol, 4-nitrophenol, 4-hydroxybiphenyl) and phenylpropanoids (naringenin, coumarins) (PubMed:7835232). Catalyzes the glucuronidation of monoterpenoid alcohols such as borneol, menthol and isomenthol, a class of natural compounds used in essential oils (By similarity)
Specific Function: Glucuronosyltransferase activity
Gene Name: UGT2B15
Uniprot ID: P54855
Uniprot Name: UDP-glucuronosyltransferase 2B15
Molecular Weight: 61035.815 Da

References

Lutz JD, Isoherranen N: Prediction of relative in vivo metabolite exposure from in vitro data using two model drugs: dextromethorphan and omeprazole. Drug Metab Dispos. 2012 Jan;40(1):159-68. doi: 10.1124/dmd.111.042200. Epub 2011 Oct 18. [Article]

Details10. UDP-glucuronosyltransferase 2B17

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: UDP-glucuronosyltransferase (UGT) that catalyzes phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase the metabolite's water solubility, thereby facilitating excretion into either the urine or bile (PubMed:16595710, PubMed:18719240, PubMed:19022937, PubMed:23288867, PubMed:8798464). Catalyzes the glucuronidation of endogenous steroid hormones such as androgens (epitestosterone, androsterone) and estrogens (estradiol, epiestradiol) (PubMed:16595710, PubMed:18719240, PubMed:19022937, PubMed:23288867, PubMed:8798464)
Specific Function: Glucuronosyltransferase activity
Gene Name: UGT2B17
Uniprot ID: O75795
Uniprot Name: UDP-glucuronosyltransferase 2B17
Molecular Weight: 61094.915 Da

References

Lutz JD, Isoherranen N: Prediction of relative in vivo metabolite exposure from in vitro data using two model drugs: dextromethorphan and omeprazole. Drug Metab Dispos. 2012 Jan;40(1):159-68. doi: 10.1124/dmd.111.042200. Epub 2011 Oct 18. [Article]

Drug created at June 13, 2005 13:24 / Updated at September 13, 2024 02:19

Dextromethorphan

Identification

Structure for Dextromethorphan (DB00514)

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Clinical Trial & Rare Diseases Add-on Data Package

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