Dexchlorpheniramine maleate

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
External IDs
Not Available
Product Ingredients
Not Available
Approved Prescription Products
Not Available
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Dexchlorpheniramine MaleateSolution2 mg/5mLOralMorton Grove Pharmaceuticals, Inc.1984-03-23Not applicableUs
Approved 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
Unapproved/Other Products
Not Available
International/Other Brands
Not Available
Brand mixtures
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Abanatuss PedSolutionOralKramer Novis.2015-07-01Not applicableUs
Abanatuss Ped DropsSolutionOralKramer Novis.2015-08-05Not applicableUs
Abatuss DmxLiquidOralKramer Novis.2014-05-25Not applicableUs
DELTUSS DMX Cough Suppressant Nasal Decongestant Antihistamine GRAPE FlavorLiquidOralDeliz Pharmaceutical Corp2015-03-20Not applicableUs
DELTUSS DP Nasal Decongestant Antihistamine CHERRY FlavorLiquidOralDeliz Pharmaceutical Corp2015-03-20Not applicableUs
Panatuss PEDLiquidOralSeyer Pharmatec, Inc.2012-12-15Not applicableUs
Pro-red AcSyrupOralPro Pharma, Llc2013-09-30Not applicableUs
ResconTablet, multilayerOralCapellon Pharmaceuticals, LLC2012-03-30Not applicableUs
RymedTablet, coatedOralEdwards Pharmaceuticals, Inc2011-11-15Not applicableUs
VanacofLiquidOralGm Pharmaceuticals2008-04-22Not applicableUs
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
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.

Structured Indications
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
DrugInteractionDrug group
2,5-Dimethoxy-4-ethylamphetamine2,5-Dimethoxy-4-ethylamphetamine may decrease the sedative activities of Dexchlorpheniramine maleate.Experimental, Illicit
3,4-Methylenedioxyamphetamine3,4-Methylenedioxyamphetamine may decrease the sedative activities of Dexchlorpheniramine maleate.Experimental, Illicit
3,4-Methylenedioxymethamphetamine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Dexchlorpheniramine maleate.Experimental, Illicit
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may decrease the sedative activities of Dexchlorpheniramine maleate.Experimental, Illicit
AmphetamineAmphetamine may decrease the sedative activities of Dexchlorpheniramine maleate.Approved, Illicit
BenzphetamineBenzphetamine may decrease the sedative activities of Dexchlorpheniramine maleate.Approved, Illicit
Benzylpenicilloyl PolylysineDexchlorpheniramine maleate may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.Approved
BetahistineThe therapeutic efficacy of Betahistine can be decreased when used in combination with Dexchlorpheniramine maleate.Approved
ChlorphentermineChlorphentermine may decrease the sedative activities of Dexchlorpheniramine maleate.Illicit, Withdrawn
DextroamphetamineDextroamphetamine may decrease the sedative activities of Dexchlorpheniramine maleate.Approved, Illicit
DiethylpropionDiethylpropion may decrease the sedative activities of Dexchlorpheniramine maleate.Approved, Illicit
HyaluronidaseThe therapeutic efficacy of Hyaluronidase can be decreased when used in combination with Dexchlorpheniramine maleate.Approved, Investigational
HydroxyamphetamineHydroxyamphetamine hydrobromide may decrease the sedative activities of Dexchlorpheniramine maleate.Approved
LisdexamfetamineLisdexamfetamine may decrease the sedative activities of Dexchlorpheniramine maleate.Approved, Investigational
MephedroneMephedrone may decrease the sedative activities of Dexchlorpheniramine maleate.Investigational
MephentermineMephentermine may decrease the sedative activities of Dexchlorpheniramine maleate.Approved
MethamphetamineMethamphetamine may decrease the sedative activities of Dexchlorpheniramine maleate.Approved, Illicit
MMDAMMDA may decrease the sedative activities of Dexchlorpheniramine maleate.Experimental, Illicit
PhenterminePhentermine may decrease the sedative activities of Dexchlorpheniramine maleate.Approved, Illicit
PseudoephedrinePseudoephedrine may decrease the sedative activities of Dexchlorpheniramine maleate.Approved
RitobegronRitobegron may decrease the sedative activities of Dexchlorpheniramine maleate.Investigational
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
ChemSpider
4444527
ChEBI
4465
ChEMBL
CHEMBL1200927
ATC Codes
Not Available
AHFS Codes
Not Available
PDB Entries
Not Available
FDA label
Not Available
MSDS
Not Available

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

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

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted LC-MS/MS Spectrum - 10V, PositivePredicted LC-MS/MSNot Available
Predicted LC-MS/MS Spectrum - 20V, PositivePredicted LC-MS/MSNot Available
Predicted LC-MS/MS Spectrum - 40V, PositivePredicted LC-MS/MSNot Available
Predicted LC-MS/MS Spectrum - 10V, NegativePredicted LC-MS/MSNot Available
Predicted LC-MS/MS Spectrum - 20V, NegativePredicted LC-MS/MSNot Available
Predicted LC-MS/MS Spectrum - 40V, NegativePredicted 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 September 01, 2017 12:06