Dexchlorpheniramine

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Summary

Dexchlorpheniramine is a chlorpheniramine enantiomer antihistamine indicated in the treatment of sunburns, insect bites, and allergic reactions of the skin.

Generic Name
Dexchlorpheniramine
DrugBank Accession Number
DB13679
Background

Dexchlorpheniramine is a potent S-enantiomer of chlorpheniramine. The salt form dexchlorpheniramine maleate as the active ingredient is available as a prescription drug indicated for adjunctive therapy for allergic and anaphylactic reactions. It is an antihistamine drug with anticholinergic (drying) and sedative actions. It disrupts histamine signaling by competing with histamine for cell receptor sites on effector cells.

Type
Small Molecule
Groups
Experimental, Investigational
Structure
Thumb
Weight
Average: 274.79
Monoisotopic: 274.1236763
Chemical Formula
C16H19ClN2
Synonyms
  • Dexchlorpheniramine
  • dexclorfeniramina

Pharmacology

Indication

Not Available

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Adverseeffects
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Toxicity

Not Available

Pathways
PathwayCategory
Dexchlorpheniramine H1-Antihistamine ActionDrug action
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
AbataceptThe metabolism of Dexchlorpheniramine can be increased when combined with Abatacept.
AbirateroneThe metabolism of Dexchlorpheniramine can be decreased when combined with Abiraterone.
AcebutololThe metabolism of Dexchlorpheniramine can be decreased when combined with Acebutolol.
AcetazolamideThe therapeutic efficacy of Acetazolamide can be decreased when used in combination with Dexchlorpheniramine.
AcrivastineThe risk or severity of QTc prolongation can be increased when Acrivastine is combined with Dexchlorpheniramine.
AdalimumabThe metabolism of Dexchlorpheniramine can be increased when combined with Adalimumab.
AdenosineThe risk or severity of QTc prolongation can be increased when Adenosine is combined with Dexchlorpheniramine.
AjmalineThe risk or severity of QTc prolongation can be increased when Ajmaline is combined with Dexchlorpheniramine.
AlfuzosinThe risk or severity of QTc prolongation can be increased when Alfuzosin is combined with Dexchlorpheniramine.
AlimemazineThe risk or severity of QTc prolongation can be increased when Alimemazine is combined with Dexchlorpheniramine.
Interactions
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Food Interactions
Not Available

Products

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Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Dextromethorphan Tannate, Phenylephrine Tannate, Dexchlorpheniramine TannateDexchlorpheniramine (2 mg/5mL) + Dextromethorphan (30 mg/5mL) + Phenylephrine (20 mg/5mL)SuspensionOralRiver's Edge Pharmaceuticals, LLC2008-08-012010-07-31US flag

Categories

ATC Codes
R06AB52 — Dexchlorpheniramine, combinationsR06AB02 — Dexchlorpheniramine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as pheniramines. These are compounds containing a pheniramine moiety, which is structurally characterized by the presence of a 2-benzylpyridine linked to an dimethyl(propyl)amine to form a dimethyl[3-phenyl-3-(pyridin-2-yl)propyl]amine skeleton.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyridines and derivatives
Sub Class
Pheniramines
Direct Parent
Pheniramines
Alternative Parents
Chlorobenzenes / Aralkylamines / Aryl chlorides / Heteroaromatic compounds / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Organochlorides / Hydrocarbon derivatives
Substituents
Amine / Aralkylamine / Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzenoid / Chlorobenzene / Halobenzene / Heteroaromatic compound
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
chlorphenamine (CHEBI:4464)
Affected organisms
Not Available

Chemical Identifiers

UNII
3Q9Q0B929N
CAS number
25523-97-1
InChI Key
SOYKEARSMXGVTM-HNNXBMFYSA-N
InChI
InChI=1S/C16H19ClN2/c1-19(2)12-10-15(16-5-3-4-11-18-16)13-6-8-14(17)9-7-13/h3-9,11,15H,10,12H2,1-2H3/t15-/m0/s1
IUPAC Name
[(3S)-3-(4-chlorophenyl)-3-(pyridin-2-yl)propyl]dimethylamine
SMILES
CN(C)CC[C@@H](C1=CC=C(Cl)C=C1)C1=CC=CC=N1

References

General References
  1. INVIMA Product Authorization: Coricidin (acetaminophen/dexchlorpheniramine maleate) oral pediatric drops [Link]
  2. AIFA Package Leaflet: POLARAMIN (Dexchlorpheniramine) for oral or topical use [Link]
Human Metabolome Database
HMDB0240218
KEGG Compound
C06946
PubChem Compound
33036
PubChem Substance
347829309
ChemSpider
30576
RxNav
22697
ChEBI
4464
ChEMBL
CHEMBL1201353
ZINC
ZINC000000113404
Wikipedia
Dexchlorpheniramine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentProstate Cancer1
3Active Not RecruitingTreatmentMultiple Sclerosis1
3CompletedPreventionHemodynamics Instability / Vasoplegic Syndrome1
3CompletedTreatmentAllergic Rhinitis (Disorder)1
3Not Yet RecruitingTreatmentLupus Nephritis / Systemic Lupus Erythematosus (SLE)1
3TerminatedTreatmentCutaneous Hypersensitivity1
3Unknown StatusTreatmentAllergic Rhinitis (Disorder)1
3Unknown StatusTreatmentInsect Bites2
3Unknown StatusTreatmentSunburn2
3Unknown StatusTreatmentViral Infections of the Upper Respiratory Tract1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
SolutionOral
SuspensionOral
SyrupOral
SyrupOral
TabletOral
SyrupOral0.04 g
TabletOral3 mg
TabletOral2 mg
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 Count5ChemAxon
Refractivity80.85 m3·mol-1ChemAxon
Polarizability30.82 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 GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-001i-0190000000-f6ef5e736260c9c22a16
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0uy0-0960000000-24a36e80af50293ed70d

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Curator comments
Enzyme information for dexchlorpheniramine is extrapolated from evidence for its enantiomer, chlorpheniramine, which likely shows the same CYP enzyme action.
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. 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. [Article]
  2. 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. [Article]

Drug created on June 23, 2017 20:46 / Updated on May 29, 2021 18:12