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
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Dexchlorpheniramine MaleateSolution2 mg/5mLOralMorton Grove Pharmaceuticals, Inc.1984-03-232017-10-21Us
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
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 (.5 mg/mL) + Chlophedianol hydrochloride (6.25 mg/mL) + Pseudoephedrine hydrochloride (15 mg/mL)SolutionOralKramer Novis.2015-08-05Not applicableUs
Abatuss DmxDexchlorpheniramine maleate (1 mg/5mL) + Dextromethorphan hydrobromide (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 (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
Panatuss PEDDexchlorpheniramine maleate (2 mg/5mL) + Chlophedianol hydrochloride (25 mg/5mL) + Pseudoephedrine hydrochloride (60 mg/5mL)LiquidOralSeyer Pharmatec, Inc.2012-12-15Not applicableUs
Panatuss PEDDexchlorpheniramine maleate (.5 mg/mL) + Chlophedianol hydrochloride (6.25 mg/mL) + Pseudoephedrine hydrochloride (15 mg/mL)Solution / dropsOralSeyer Pharmatec, Inc.2012-12-15Not applicableUs
Pro-red AcDexchlorpheniramine maleate (1 mg/5mL) + Codeine phosphate (9 mg/5mL) + Phenylephrine hydrochloride (5 mg/5mL)SyrupOralPro Pharma, Llc2013-09-30Not applicableUs
ResconDexchlorpheniramine maleate (2 mg/1) + Pseudoephedrine hydrochloride (60 mg/1)Tablet, multilayerOralCapellon Pharmaceuticals, LLC2012-03-30Not applicableUs
RymedDexchlorpheniramine maleate (2 mg/1) + Phenylephrine hydrochloride (10 mg/1)Tablet, coatedOralEdwards Pharmaceuticals, Inc2011-11-15Not 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
(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

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
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may decrease the sedative activities of Dexchlorpheniramine maleate.Experimental, Illicit
AbirateroneThe serum concentration of Dexchlorpheniramine maleate can be increased when it is combined with Abiraterone.Approved
AmiodaroneThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Amiodarone.Approved, Investigational
AmphetamineAmphetamine may decrease the sedative activities of Dexchlorpheniramine maleate.Approved, Illicit
AprepitantThe serum concentration of Dexchlorpheniramine maleate can be increased when it is combined with Aprepitant.Approved, Investigational
ArtemetherThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Artemether.Approved
AtazanavirThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Atazanavir.Approved, Investigational
AtomoxetineThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Atomoxetine.Approved
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
BetaxololThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Betaxolol.Approved
BoceprevirThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Boceprevir.Approved, Withdrawn
BortezomibThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Dexchlorpheniramine maleate can be decreased when it is combined with Bosentan.Approved, Investigational
BupropionThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Bupropion.Approved
CarbamazepineThe metabolism of Dexchlorpheniramine maleate can be increased when combined with Carbamazepine.Approved, Investigational
CelecoxibThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Celecoxib.Approved, Investigational
CeritinibThe serum concentration of Dexchlorpheniramine maleate can be increased when it is combined with Ceritinib.Approved
ChloroquineThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Chloroquine.Approved, Vet Approved
ChlorphentermineChlorphentermine may decrease the sedative activities of Dexchlorpheniramine maleate.Illicit, Withdrawn
ChlorpromazineThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Chlorpromazine.Approved, Vet Approved
CholecalciferolThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
CimetidineThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Cimetidine.Approved
CinacalcetThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Cinacalcet.Approved
CitalopramThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Citalopram.Approved
ClarithromycinThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Clemastine.Approved
ClobazamThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Clobazam.Approved, Illicit
ClomipramineThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Clomipramine.Approved, Vet Approved
ClotrimazoleThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Clotrimazole.Approved, Vet Approved
ClozapineThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Clozapine.Approved
CobicistatThe serum concentration of Dexchlorpheniramine maleate can be increased when it is combined with Cobicistat.Approved
CocaineThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Cocaine.Approved, Illicit
ConivaptanThe serum concentration of Dexchlorpheniramine maleate can be increased when it is combined with Conivaptan.Approved, Investigational
CrizotinibThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Crizotinib.Approved
CyclosporineThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
DabrafenibThe serum concentration of Dexchlorpheniramine maleate can be decreased when it is combined with Dabrafenib.Approved
DarifenacinThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Darifenacin.Approved, Investigational
DarunavirThe serum concentration of Dexchlorpheniramine maleate can be increased when it is combined with Darunavir.Approved
DasatinibThe serum concentration of Dexchlorpheniramine maleate can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Dexchlorpheniramine maleate can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Delavirdine.Approved
DesipramineThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Desipramine.Approved
DextroamphetamineDextroamphetamine may decrease the sedative activities of Dexchlorpheniramine maleate.Approved, Illicit
DiethylpropionDiethylpropion may decrease the sedative activities of Dexchlorpheniramine maleate.Approved, Illicit
DihydroergotamineThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Dihydroergotamine.Approved
DiltiazemThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Diltiazem.Approved
DiphenhydramineThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Diphenhydramine.Approved
DosulepinThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Dosulepin.Approved
DoxycyclineThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Dronedarone.Approved
DuloxetineThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Duloxetine.Approved
EliglustatThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Eliglustat.Approved
EnzalutamideThe serum concentration of Dexchlorpheniramine maleate can be decreased when it is combined with Enzalutamide.Approved
ErythromycinThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Erythromycin.Approved, Vet Approved
FesoterodineThe serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination with Dexchlorpheniramine maleate.Approved
FluconazoleThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Fluconazole.Approved
FluoxetineThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Fluoxetine.Approved, Vet Approved
FluvoxamineThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Dexchlorpheniramine maleate can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe metabolism of Dexchlorpheniramine maleate can be increased when combined with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Dexchlorpheniramine maleate can be increased when it is combined with Fusidic Acid.Approved
GepefrineGepefrine may decrease the sedative activities of Dexchlorpheniramine maleate.Experimental
HaloperidolThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Haloperidol.Approved
HyaluronidaseThe therapeutic efficacy of Hyaluronidase can be decreased when used in combination with Dexchlorpheniramine maleate.Approved, Investigational
HydroxyamphetamineHydroxyamphetamine may decrease the sedative activities of Dexchlorpheniramine maleate.Approved
IdelalisibThe serum concentration of Dexchlorpheniramine maleate can be increased when it is combined with Idelalisib.Approved
ImatinibThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Imatinib.Approved
ImipramineThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Imipramine.Approved
IndinavirThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Indinavir.Approved
Iofetamine I-123Iofetamine I-123 may decrease the sedative activities of Dexchlorpheniramine maleate.Approved
IsavuconazoniumThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Isavuconazonium.Approved, Investigational
IsoniazidThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Isoniazid.Approved
IsradipineThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Isradipine.Approved
ItraconazoleThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Dexchlorpheniramine maleate can be increased when it is combined with Ivacaftor.Approved
KetoconazoleThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Ketoconazole.Approved, Investigational
LisdexamfetamineLisdexamfetamine may decrease the sedative activities of Dexchlorpheniramine maleate.Approved, Investigational
LopinavirThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Lopinavir.Approved
LorcaserinThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Lorcaserin.Approved
LovastatinThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Dexchlorpheniramine maleate can be increased when it is combined with Luliconazole.Approved
LumacaftorThe metabolism of Dexchlorpheniramine maleate can be increased when combined with Lumacaftor.Approved
LumefantrineThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Lumefantrine.Approved
ManidipineThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Manidipine.Approved, Investigational
MephedroneMephedrone may decrease the sedative activities of Dexchlorpheniramine maleate.Investigational
MephentermineMephentermine may decrease the sedative activities of Dexchlorpheniramine maleate.Approved
MethadoneThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Methadone.Approved
MethamphetamineMethamphetamine may decrease the sedative activities of Dexchlorpheniramine maleate.Approved, Illicit
MethotrimeprazineThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Methotrimeprazine.Approved
MethoxyphenamineMethoxyphenamine may decrease the sedative activities of Dexchlorpheniramine maleate.Experimental
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Dexchlorpheniramine maleate.Approved, Investigational
Midomafetamine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Dexchlorpheniramine maleate.Experimental, Illicit, Investigational
MidostaurinThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Midostaurin.Approved
MifepristoneThe serum concentration of Dexchlorpheniramine maleate can be increased when it is combined with Mifepristone.Approved, Investigational
MirabegronThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Mirabegron.Approved
MitotaneThe serum concentration of Dexchlorpheniramine maleate can be decreased when it is combined with Mitotane.Approved
MMDAMMDA may decrease the sedative activities of Dexchlorpheniramine maleate.Experimental, Illicit
NefazodoneThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Nelfinavir.Approved
NetupitantThe serum concentration of Dexchlorpheniramine maleate can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Dexchlorpheniramine maleate can be increased when combined with Nevirapine.Approved
NicardipineThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Nicardipine.Approved
NilotinibThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Nilotinib.Approved, Investigational
OlaparibThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Olaparib.Approved
OsimertinibThe serum concentration of Dexchlorpheniramine maleate can be increased when it is combined with Osimertinib.Approved
PalbociclibThe serum concentration of Dexchlorpheniramine maleate can be increased when it is combined with Palbociclib.Approved
PanobinostatThe serum concentration of Dexchlorpheniramine maleate can be increased when it is combined with Panobinostat.Approved, Investigational
ParoxetineThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Paroxetine.Approved, Investigational
Peginterferon alfa-2bThe serum concentration of Dexchlorpheniramine maleate can be decreased when it is combined with Peginterferon alfa-2b.Approved
PentobarbitalThe metabolism of Dexchlorpheniramine maleate can be increased when combined with Pentobarbital.Approved, Vet Approved
PhenobarbitalThe metabolism of Dexchlorpheniramine maleate can be increased when combined with Phenobarbital.Approved
PhenterminePhentermine may decrease the sedative activities of Dexchlorpheniramine maleate.Approved, Illicit
PhenytoinThe metabolism of Dexchlorpheniramine maleate can be increased when combined with Phenytoin.Approved, Vet Approved
PosaconazoleThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PrimidoneThe metabolism of Dexchlorpheniramine maleate can be increased when combined with Primidone.Approved, Vet Approved
PromazineThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Promazine.Approved, Vet Approved
PseudoephedrinePseudoephedrine may decrease the sedative activities of Dexchlorpheniramine maleate.Approved
QuinidineThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Quinidine.Approved
QuinineThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Quinine.Approved
RanolazineThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Ranolazine.Approved, Investigational
RifabutinThe metabolism of Dexchlorpheniramine maleate can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Dexchlorpheniramine maleate can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Dexchlorpheniramine maleate can be increased when combined with Rifapentine.Approved
RitobegronRitobegron may decrease the sedative activities of Dexchlorpheniramine maleate.Investigational
RitonavirThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Ritonavir.Approved, Investigational
RolapitantThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Rolapitant.Approved
RopiniroleThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Ropinirole.Approved, Investigational
SaquinavirThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Saquinavir.Approved, Investigational
SertralineThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Sertraline.Approved
SildenafilThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Dexchlorpheniramine maleate can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Dexchlorpheniramine maleate can be increased when it is combined with Simeprevir.Approved
St. John's WortThe serum concentration of Dexchlorpheniramine maleate can be decreased when it is combined with St. John's Wort.Investigational, Nutraceutical
StiripentolThe serum concentration of Dexchlorpheniramine maleate can be increased when it is combined with Stiripentol.Approved
SulfisoxazoleThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
TelaprevirThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Telaprevir.Approved, Withdrawn
TelithromycinThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Telithromycin.Approved
TerbinafineThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Terbinafine.Approved, Investigational, Vet Approved
ThioridazineThe serum concentration of Thioridazine can be increased when it is combined with Dexchlorpheniramine maleate.Approved, Withdrawn
TiclopidineThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Ticlopidine.Approved
TipranavirThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Tipranavir.Approved, Investigational
TocilizumabThe serum concentration of Dexchlorpheniramine maleate can be decreased when it is combined with Tocilizumab.Approved
TranylcypromineThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Tranylcypromine.Approved
VenlafaxineThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Verapamil.Approved
VoriconazoleThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Voriconazole.Approved, Investigational
ZiprasidoneThe metabolism of Dexchlorpheniramine maleate can be decreased when combined with Ziprasidone.Approved
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

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
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 09, 2017 04:50