Identification

Name
Dexchlorpheniramine maleate
Accession Number
DB09555
Type
Small Molecule
Groups
Approved
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.

Structure
Thumb
Synonyms
Not Available
Active Moieties
NameKindUNIICASInChI Key
Dexchlorpheniramineprodrug3Q9Q0B929N25523-97-1SOYKEARSMXGVTM-HNNXBMFYSA-N
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Dexchlorpheniramine MaleateSolution2 mg/5mLOralMorton Grove Pharmaceuticals, Inc.1984-03-232012-11-08Us
PolmonSolution2 mg/5mLOralCapellon Pharmaceuticals, LLC2018-07-16Not applicableUs
RycloraLiquid2 mg/5mLOralCarWin Pharmaceutical Associates, LLC2018-10-07Not applicableUs
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Polaramine Repetabs 6mgTablet, extended release6 mgOralSchering Plough1958-12-311997-12-02Canada
Polaramine Tab 2mgTablet2 mgOralSchering Plough1959-12-312002-07-12Canada
Rescon MXTablet2 mg/1OralCapellon Pharmaceuticals, LLC2011-12-282013-07-31Us
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Abanatuss PedDexchlorpheniramine maleate (2 mg/5mL) + Chlophedianol hydrochloride (25 mg/5mL) + Pseudoephedrine hydrochloride (60 mg/5mL)SolutionOralKramer Novis.2015-07-01Not applicableUs
Abanatuss Ped DropsDexchlorpheniramine maleate (0.5 mg/1mL) + Chlophedianol hydrochloride (6.25 mg/1mL) + Pseudoephedrine hydrochloride (15 mg/1mL)SolutionOralKramer Novis.2015-08-05Not applicableUs
Abatuss DmxDexchlorpheniramine maleate (1 mg/5mL) + Dextromethorphan hydrobromide monohydrate (15 mg/5mL) + Pseudoephedrine hydrochloride (30 mg/5mL)LiquidOralKramer Novis.2014-05-25Not applicableUs
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
DELTUSS DP Nasal Decongestant Antihistamine CHERRY FlavorDexchlorpheniramine maleate (1 mg/5mL) + Pseudoephedrine hydrochloride (30 mg/5mL)LiquidOralDeliz Pharmaceutical Corp2015-03-20Not applicableUs
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
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
Panatuss PEDDexchlorpheniramine maleate (2 mg/5mL) + Chlophedianol hydrochloride (25 mg/5mL) + Pseudoephedrine hydrochloride (60 mg/5mL)LiquidOralSeyer Pharmatec, Inc.2012-12-15Not applicableUs
Polytussin DMDexchlorpheniramine maleate (1 mg/5mL) + Dextromethorphan hydrobromide monohydrate (10 mg/5mL) + Phenylephrine hydrochloride (5 mg/5mL)SyrupOralPoly Pharmaceuticals2017-11-22Not applicableUs
Pro-red AcDexchlorpheniramine maleate (1 mg/5mL) + Codeine phosphate hemihydrate (9 mg/5mL) + Phenylephrine hydrochloride (5 mg/5mL)SyrupOralPro-Pharma, LLC2013-09-30Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Corzall PEDexchlorpheniramine maleate (1 mg/5mL) + Pentoxyverine citrate (20 mg/5mL) + Phenylephrine hydrochloride (10 mg/5mL)LiquidOralHawthorn Pharmaceuticals, Inc.2010-09-222011-08-26Us
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
Rescon JrDexchlorpheniramine maleate (3 mg/1) + Phenylephrine hydrochloride (20 mg/1)Tablet, multilayer, extended releaseOralCapellon Pharmaceuticals, LLC2010-01-212012-04-30Us
Rescon MXDexchlorpheniramine maleate (6 mg/1) + Phenylephrine hydrochloride (40 mg/1)Tablet, multilayer, extended releaseOralCapellon Pharmaceuticals, LLC2010-01-212013-04-30Us
Categories
UNII
B10YD955QW
CAS number
Not Available
Weight
Average: 390.86
Monoisotopic: 390.1346349
Chemical Formula
C20H23ClN2O4
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[C@@H](C1=CC=C(Cl)C=C1)C1=CC=CC=N1

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
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
Human
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

Toxicity

Central nervous system depression

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

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with (R)-warfarin.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Dexchlorpheniramine maleate.
2,5-Dimethoxy-4-ethylamphetamine2,5-Dimethoxy-4-ethylamphetamine may decrease the sedative and stimulatory activities of Dexchlorpheniramine maleate.
2,5-Dimethoxy-4-ethylthioamphetamine2,5-Dimethoxy-4-ethylthioamphetamine may decrease the sedative and stimulatory activities of Dexchlorpheniramine maleate.
3,4-Methylenedioxyamphetamine3,4-Methylenedioxyamphetamine may decrease the sedative and stimulatory activities of Dexchlorpheniramine maleate.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Dexchlorpheniramine maleate.
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may decrease the sedative and stimulatory activities of Dexchlorpheniramine maleate.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Dexchlorpheniramine maleate.
4-MethoxyamphetamineThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with 4-Methoxyamphetamine.
5-androstenedioneThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with 5-androstenedione.
Food Interactions
Not Available

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]
External Links
KEGG Compound
C07783
PubChem Compound
5281070
PubChem Substance
347827879
ChemSpider
4444527
ChEBI
4465
ChEMBL
CHEMBL1200927
Wikipedia
Dexchlorpheniramine

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
SolutionOral
LiquidOral
SolutionOral2 mg/5mL
Solution / dropsOral
Tablet, extended releaseOral6 mg
TabletOral2 mg
SyrupOral
Tablet, multilayerOral
TabletOral2 mg/1
Tablet, multilayer, extended releaseOral
LiquidOral2 mg/5mL
Tablet, coatedOral
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

Taxonomy

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
Fatty acyl / Fatty acid / Unsaturated fatty acid / Dicarboxylic acid or derivatives / Carboxylic acid / Organic oxygen compound / Organic oxide / Hydrocarbon derivative / Organooxygen compound / Carbonyl group
Molecular Framework
Not Available
External Descriptors
organic molecular entity (CHEBI:4465)

Targets

Kind
Protein
Organism
Human
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
Human
Pharmacological action
No
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. 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]
Kind
Protein
Organism
Human
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
Human
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
Human
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 November 02, 2018 07:03