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

Identification

Logo pink
Are you a
new drug developer?
Contact us to learn more about our customized products and solutions.
Logo pink
Stay in the know!
As part of our commitment to providing the most up-to-date drug information, we will be releasing #DrugBankUpdates with our newly added curated drug pages.
#DrugBankUpdates
Name
Dexchlorpheniramine
Accession Number
DB13679
Type
Small Molecule
Groups
Experimental, Investigational
Description

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 adjuctive therapy for allergic and anaphylactic reactions. It is an antihistamine drug with anticholinergic (drying) and sedative actions. It disrupts histamine signalling by competing with histamine for cell receptor sites on effector cells.

Structure
Thumb
Synonyms
  • Dexchlorpheniramine
  • dexclorfeniramina
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
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
Categories
UNII
3Q9Q0B929N
CAS number
25523-97-1
Weight
Average: 274.79
Monoisotopic: 274.1236763
Chemical Formula
C16H19ClN2
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

Pharmacology

Indication
Not Available
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
Toxicity
Not Available
Affected organisms
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
1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidineThe metabolism of Dexchlorpheniramine can be decreased when combined with 1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine.
2,5-Dimethoxy-4-ethylamphetamine2,5-Dimethoxy-4-ethylamphetamine may decrease the sedative and stimulatory activities of Dexchlorpheniramine.
2,5-Dimethoxy-4-ethylthioamphetamine2,5-Dimethoxy-4-ethylthioamphetamine may decrease the sedative and stimulatory activities of Dexchlorpheniramine.
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may decrease the sedative and stimulatory activities of Dexchlorpheniramine.
4-MethoxyamphetamineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Dexchlorpheniramine.
5-methoxy-N,N-dimethyltryptamineThe metabolism of 5-methoxy-N,N-dimethyltryptamine can be decreased when combined with Dexchlorpheniramine.
7-NitroindazoleThe therapeutic efficacy of 7-Nitroindazole can be decreased when used in combination with Dexchlorpheniramine.
AbataceptThe metabolism of Dexchlorpheniramine can be increased when combined with Abatacept.
AbexinostatThe risk or severity of QTc prolongation can be increased when Abexinostat is combined with Dexchlorpheniramine.
AbirateroneThe metabolism of Dexchlorpheniramine can be decreased when combined with Abiraterone.
Additional Data Available
  • Extended Description
    Extended Description

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

    Learn more
  • Severity
    Severity

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

    Learn more
  • Evidence Level
    Evidence Level

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

    Learn more
  • Action
    Action

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

    Learn more
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0240218
KEGG Compound
C06946
PubChem Compound
33036
PubChem Substance
347829309
ChemSpider
30576
ChEBI
4464
ChEMBL
CHEMBL1201353
Wikipedia
Dexchlorpheniramine
ATC Codes
R06AB52 — Dexchlorpheniramine, combinationsR06AB02 — Dexchlorpheniramine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1Active Not RecruitingTreatmentProgressive Multiple Sclerosis1
3Active Not RecruitingPreventionHemodynamics Instability / Vasoplegic Syndrome1
3CompletedTreatmentAllergic Rhinitis (AR)1
3RecruitingTreatmentDisseminated Sclerosis1
3TerminatedTreatmentCutaneous Hypersensitivity1
3Unknown StatusTreatmentAllergic Rhinitis (AR)1
3Unknown StatusTreatmentInsect Bites2
3Unknown StatusTreatmentSunburn2
3Unknown StatusTreatmentViral Infections of the Upper Respiratory Tract1
4CompletedTreatmentProstate Cancer1
Not AvailableCompletedBasic ScienceCognition1
Not AvailableCompletedBasic SciencePain1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
SuspensionOral
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

Taxonomy

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
Pheniramine / Chlorobenzene / Halobenzene / Aralkylamine / Aryl chloride / Benzenoid / Monocyclic benzene moiety / Aryl halide / Heteroaromatic compound / Tertiary aliphatic amine
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
chlorphenamine (CHEBI:4464)

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. [PubMed:11936702]
  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. [PubMed:11994058]

Drug created on June 23, 2017 14:46 / Updated on December 02, 2019 10:03