Dexchlorpheniramine maleate

Identification

Name
Dexchlorpheniramine maleate
Accession Number
DB09555
Description

Dexchlorpheniramine is the S-enantiomer of chlorpheniramine which is a 1st generation anti-histamine. Dexchlorpheniramine has more pharmacological activity than the R and so is more potent than the racemic mixture.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 390.86
Monoisotopic: 390.1346349
Chemical Formula
C20H23ClN2O4
Synonyms
Not Available

Pharmacology

Indication

Dexchlorpheniramine can be used in the treatment of perennial and seasonal allergic rhinitis, vasomotor rhiniti, allergic conjunctivitis due to inhalant allergens and foods, mild uncomplicated allergic skin manifestations of urticaria and angioedema, amelioration of allergic reactions to blood or plasma, and dermographism.

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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Pharmacodynamics

In allergic reactions, an allergen binds to IgE antibodies on mast cells and basophils. Once this occurs IgE receptors crosslink with each other triggering a series of events that eventually leads to cell-degranulation and the release of histamine (and other chemical mediators) from the mast cell or basophil. Histamine can react with local or widespread tissues through histamine receptors. Histamine, acting on H1-receptors, produces pruritis, vasodilatation, hypotension, flushing, headache, tachycardia, and bronchoconstriction. Histamine also increases vascular permeability and potentiates pain. Dexchlorpheniramine, is a histamine H1 antagonist of the alkylamine class. It competes with histamine for the normal H1-receptor sites on effector cells of the gastrointestinal tract, blood vessels and respiratory tract. It provides effective, temporary relief of sneezing, watery and itchy eyes, and runny nose due to hay fever and other upper respiratory allergies.

Mechanism of action

Competes with histamine for H1-receptor sites on effector cells in the gastrointestinal tract, blood vessels, and respiratory tract. Dexchlorpheniramine is the predominant active isomer of chlorpheniramine and is approximately twice as active as the racemic compound.

TargetActionsOrganism
AHistamine H1 receptor
antagonist
Humans
Absorption

Oral bioavailability in rats 40.5%

Volume of distribution

321L

Protein binding

Dexchlorpheniramine is bound to total plasma proteins 38%, to albumin 20% and to alpha-glycoprotein acid 23%.

Metabolism

Hepatic metabolism. Major metabolism by CYP 2D6 and minor metabolism by 3A4, 2C11 and 2B1.

Route of elimination

Renal excretion

Half-life

20-30 h

Clearance

9.8L/h

Adverse Effects
Learn about our commercial Adverse Effects data.
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Toxicity

Central nervous system depression

Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbametapirThe serum concentration of Dexchlorpheniramine maleate can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Dexchlorpheniramine maleate can be increased when combined with Abatacept.
AbirateroneThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Abiraterone.
AcebutololThe risk or severity of QTc prolongation can be increased when Acebutolol is combined with Dexchlorpheniramine maleate.
AcetaminophenThe metabolism of Acetaminophen can be decreased when combined with Dexchlorpheniramine maleate.
AcetazolamideThe therapeutic efficacy of Acetazolamide can be decreased when used in combination with Dexchlorpheniramine maleate.
AcetylcholineThe risk or severity of adverse effects can be increased when Dexchlorpheniramine maleate is combined with Acetylcholine.
AcrivastineThe risk or severity of QTc prolongation can be increased when Acrivastine is combined with Dexchlorpheniramine maleate.
AcyclovirThe risk or severity of adverse effects can be increased when Acyclovir is combined with Dexchlorpheniramine maleate.
AdalimumabThe metabolism of Dexchlorpheniramine maleate can be increased when combined with Adalimumab.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Avoid alcohol. Alcohol may have additive CNS depressant effects with dexchlorpheniramine maleate.

Products

Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Dexchlorpheniramine MaleateSolution2 mg/5mLOralFoxland Pharmaceuticals, Inc.2018-12-19Not applicableUS flag
Dexchlorpheniramine MaleateSolution2 mg/5mLOralMorton Grove Pharmaceuticals, Inc.1984-03-232012-11-08US flag
PolmonSolution2 mg/5mLOralCapellon Pharmaceuticals, LLC2018-07-16Not applicableUS flag
RycloraLiquid2 mg/5mLOralCarWin Pharmaceutical Associates, LLC2018-10-07Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Polaramine Repetabs 6mgTablet, extended releaseOralSchering Plough1958-12-311997-12-02Canada flag
Polaramine Tab 2mgTabletOralSchering Plough1959-12-312002-07-12Canada flag
Rescon MXTablet2 mg/1OralCapellon Pharmaceuticals, LLC2011-12-282013-07-31US flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Abanatuss PedDexchlorpheniramine maleate (2 mg/5mL) + Chlophedianol hydrochloride (25 mg/5mL) + Pseudoephedrine hydrochloride (60 mg/5mL)SolutionOralKRAMER NOVIS2015-07-01Not applicableUS flag
Abanatuss Ped DropsDexchlorpheniramine maleate (0.5 mg/1mL) + Chlophedianol hydrochloride (6.25 mg/1mL) + Pseudoephedrine hydrochloride (15 mg/1mL)SolutionOralKRAMER NOVIS2015-08-05Not applicableUS flag
Abatuss DmxDexchlorpheniramine maleate (1 mg/5mL) + Dextromethorphan hydrobromide monohydrate (15 mg/5mL) + Pseudoephedrine hydrochloride (30 mg/5mL)LiquidOralKRAMER NOVIS2014-05-25Not applicableUS flag
DELTUSS DMX Cough Suppressant Nasal Decongestant Antihistamine GRAPE FlavorDexchlorpheniramine maleate (1 mg/5mL) + Dextromethorphan hydrobromide monohydrate (15 mg/5mL) + Pseudoephedrine hydrochloride (30 mg/5mL)LiquidOralDeliz Pharmaceutical Corp2015-03-20Not applicableUS flag
DELTUSS DP Nasal Decongestant Antihistamine CHERRY FlavorDexchlorpheniramine maleate (1 mg/5mL) + Pseudoephedrine hydrochloride (30 mg/5mL)LiquidOralDeliz Pharmaceutical Corp2015-03-20Not applicableUS flag
Dexphen w/ CodeineDexchlorpheniramine maleate (1 mg/5mL) + Codeine phosphate hemihydrate (10 mg/5mL) + Phenylephrine hydrochloride (5 mg/5mL)LiquidOralBreckenridge Pharmaceutical, Inc.2010-10-102010-10-10US flag
Panatuss PEDDexchlorpheniramine maleate (0.5 mg/1mL) + Chlophedianol hydrochloride (6.25 mg/1mL) + Pseudoephedrine hydrochloride (15 mg/1mL)Solution / dropsOralSeyer Pharmatec, Inc.2012-12-15Not applicableUS flag
Panatuss PEDDexchlorpheniramine maleate (2 mg/5mL) + Chlophedianol hydrochloride (25 mg/5mL) + Pseudoephedrine hydrochloride (60 mg/5mL)LiquidOralSeyer Pharmatec, Inc.2012-12-15Not applicableUS flag
Polytussin DMDexchlorpheniramine maleate (1 mg/5mL) + Dextromethorphan hydrobromide monohydrate (10 mg/5mL) + Phenylephrine hydrochloride (5 mg/5mL)SyrupOralPoly Pharmaceuticals, Inc.2017-11-22Not applicableUS flag
Pro-red AcDexchlorpheniramine maleate (1 mg/5mL) + Codeine phosphate hemihydrate (9 mg/5mL) + Phenylephrine hydrochloride (5 mg/5mL)SyrupOralPro-Pharma, LLC2013-09-30Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Corzall PEDexchlorpheniramine maleate (1 mg/5mL) + Pentoxyverine citrate (20 mg/5mL) + Phenylephrine hydrochloride (10 mg/5mL)LiquidOralHawthorn Pharmaceuticals, Inc.2010-09-222011-08-26US flag
Dexphen w/ CodeineDexchlorpheniramine maleate (1 mg/5mL) + Codeine phosphate hemihydrate (10 mg/5mL) + Phenylephrine hydrochloride (5 mg/5mL)LiquidOralBreckenridge Pharmaceutical, Inc.2010-10-102010-10-10US flag
Re DrylexDexchlorpheniramine maleate (1 mg/5mL) + Methscopolamine nitrate (1.25 mg/5mL) + Phenylephrine hydrochloride (10 mg/5mL)SyrupOralRiver's Edge Pharmaceuticals, LLC2008-11-012011-01-31US flag
Rescon JrDexchlorpheniramine maleate (3 mg/1) + Phenylephrine hydrochloride (20 mg/1)Tablet, multilayer, extended releaseOralCapellon Pharmaceuticals, LLC2010-01-212012-04-30US flag
Rescon MXDexchlorpheniramine maleate (6 mg/1) + Phenylephrine hydrochloride (40 mg/1)Tablet, multilayer, extended releaseOralCapellon Pharmaceuticals, LLC2010-01-212013-04-30US flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Dicarboxylic acids and derivatives
Direct Parent
Dicarboxylic acids and derivatives
Alternative Parents
Unsaturated fatty acids / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Aromatic heteromonocyclic compound / Carbonyl group / Carboxylic acid / Dicarboxylic acid or derivatives / Fatty acid / Fatty acyl / Hydrocarbon derivative / Organic oxide / Organic oxygen compound / Organooxygen compound
Molecular Framework
Not Available
External Descriptors
organic molecular entity (CHEBI:4465)

Chemical Identifiers

UNII
B10YD955QW
CAS number
2438-32-6
InChI Key
DBAKFASWICGISY-DASCVMRKSA-N
InChI
InChI=1S/C16H19ClN2.C4H4O4/c1-19(2)12-10-15(16-5-3-4-11-18-16)13-6-8-14(17)9-7-13;5-3(6)1-2-4(7)8/h3-9,11,15H,10,12H2,1-2H3;1-2H,(H,5,6)(H,7,8)/b;2-1-/t15-;/m0./s1
IUPAC Name
(2Z)-but-2-enedioic acid; [(3S)-3-(4-chlorophenyl)-3-(pyridin-2-yl)propyl]dimethylamine
SMILES
OC(=O)\C=C/C(O)=O.CN(C)CC[[email protected]@H](C1=CC=C(Cl)C=C1)C1=CC=CC=N1

References

Synthesis Reference

LI Pengfei LIU Lihong MA Ping WANG LingCHI Xiaohua LIANG Dongmei GAO Wenjing WANG Yanfeng(Department of Pharmacy,the Second Artillery General Hospital,PLA,100088,Beijing,China);PHARMACOKINETICS OF PARACETAMOL AND DEXCHLORPHENIRAMINE MALEATE ORAL SOLUTION IN HEALTHY VOLUNTEERS[J];Journal of Beijing Normal University(Natural Science);2008-03

Zuberbier T, Aberer W, Asero R, et al. The EAACI/GA(2) LEN/EDF/WAO guideline for the definition, classification, diagnosis, and management of urticaria: the 2013 revision and update. Allergy. 2014;69(7):868-887.

General References
  1. Angier E, Willington J, Scadding G, Holmes S, Walker S: Management of allergic and non-allergic rhinitis: a primary care summary of the BSACI guideline. Prim Care Respir J. 2010 Sep;19(3):217-22. doi: 10.4104/pcrj.2010.00044. [PubMed:20680237]
  2. Bui TH, Fernandez C, Vu K, Nguyen KH, Thuillier A, Farinotti R, Arnaud P, Gimenez F: Stereospecific versus nonstereospecific assessments for the bioequivalence of two formulations of racemic chlorpheniramine. Chirality. 2000 Aug;12(8):599-605. [PubMed:10897096]
  3. Huang SM, Athanikar NK, Sridhar K, Huang YC, Chiou WL: Pharmacokinetics of chlorpheniramine after intravenous and oral administration in normal adults. Eur J Clin Pharmacol. 1982;22(4):359-65. [PubMed:7106172]
  4. Hiep BT, Gimenez F, Khanh VU, Hung NK, Thuillier A, Farinotti R, Fernandez C: Binding of chlorpheniramine enantiomers to human plasma proteins. Chirality. 1999;11(5-6):501-4. [PubMed:10368923]
  5. Nomura A, Sakurai E, Hikichi N: Stereoselective N-demethylation of chlorpheniramine by rat-liver microsomes and the involvement of cytochrome P450 isozymes. J Pharm Pharmacol. 1997 Mar;49(3):257-62. [PubMed:9231341]
  6. Dexchlorpheniramine monograph [Link]
KEGG Compound
C07783
PubChem Compound
5281070
PubChem Substance
347827879
ChemSpider
4444527
RxNav
54828
ChEBI
4465
ChEMBL
CHEMBL1200927
Wikipedia
Dexchlorpheniramine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
Not AvailableCompletedBasic SciencePain1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
SolutionOral
Capsule
LiquidOral
Tablet
SolutionOral2 mg/5mL
Solution / dropsOral
Tablet, extended releaseOral
TabletOral
SyrupOral
Tablet, multilayerOral
TabletOral2 mg/1
Tablet, multilayer, extended releaseOral
LiquidOral2 mg/5mL
Tablet, coatedOral
SyrupOral
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0519 mg/mLALOGPS
logP3.74ALOGPS
logP3.58ChemAxon
logS-3.7ALOGPS
pKa (Strongest Basic)9.47ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area16.13 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity80.85 m3·mol-1ChemAxon
Polarizability30.81 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Histamine receptor activity
Specific Function
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamin...
Gene Name
HRH1
Uniprot ID
P35367
Uniprot Name
Histamine H1 receptor
Molecular Weight
55783.61 Da

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Inhibitor
Curator comments
This enzyme action was extrapolated from data regarding chlorpheniramine, dexchlorpheniramine's enantiomer, which likely shares the same CYP enzyme activity.
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Yasuda SU, Zannikos P, Young AE, Fried KM, Wainer IW, Woosley RL: The roles of CYP2D6 and stereoselectivity in the clinical pharmacokinetics of chlorpheniramine. Br J Clin Pharmacol. 2002 May;53(5):519-25. [PubMed:11994058]
  2. He N, Zhang WQ, Shockley D, Edeki T: Inhibitory effects of H1-antihistamines on CYP2D6- and CYP2C9-mediated drug metabolic reactions in human liver microsomes. Eur J Clin Pharmacol. 2002 Feb;57(12):847-51. [PubMed:11936702]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Secondary active organic cation transmembrane transporter activity
Specific Function
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnico...
Gene Name
SLC22A1
Uniprot ID
O15245
Uniprot Name
Solute carrier family 22 member 1
Molecular Weight
61153.345 Da
References
  1. Urakami Y, Okuda M, Masuda S, Akazawa M, Saito H, Inui K: Distinct characteristics of organic cation transporters, OCT1 and OCT2, in the basolateral membrane of renal tubules. Pharm Res. 2001 Nov;18(11):1528-34. [PubMed:11758759]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Quaternary ammonium group transmembrane transporter activity
Specific Function
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
Gene Name
SLC22A2
Uniprot ID
O15244
Uniprot Name
Solute carrier family 22 member 2
Molecular Weight
62579.99 Da
References
  1. Urakami Y, Okuda M, Masuda S, Akazawa M, Saito H, Inui K: Distinct characteristics of organic cation transporters, OCT1 and OCT2, in the basolateral membrane of renal tubules. Pharm Res. 2001 Nov;18(11):1528-34. [PubMed:11758759]

Drug created on November 30, 2015 12:10 / Updated on June 12, 2020 10:52

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