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
Structure for Dexchlorpheniramine (DB13679)
- Weight
- Average: 274.79
Monoisotopic: 274.1236763 - Chemical Formula
- C16H19ClN2
- Synonyms
- Dexchlorpheniramine
- dexclorfeniramina
Pharmacology
- Indication
Not Available
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- Contraindications & Blackbox Warnings
Contraindications & Blackbox WarningsWith our commercial data, access important information on dangerous risks, contraindications, and adverse effects.Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects- 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
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Not Available
- Pathways
Pathway Category Dexchlorpheniramine H1-Antihistamine Action Drug 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbatacept The metabolism of Dexchlorpheniramine can be increased when combined with Abatacept. Abiraterone The metabolism of Dexchlorpheniramine can be decreased when combined with Abiraterone. Acebutolol The metabolism of Dexchlorpheniramine can be decreased when combined with Acebutolol. Acetazolamide The therapeutic efficacy of Acetazolamide can be decreased when used in combination with Dexchlorpheniramine. Acrivastine The risk or severity of QTc prolongation can be increased when Acrivastine is combined with Dexchlorpheniramine. Adalimumab The metabolism of Dexchlorpheniramine can be increased when combined with Adalimumab. Adenosine The risk or severity of QTc prolongation can be increased when Adenosine is combined with Dexchlorpheniramine. Ajmaline The risk or severity of QTc prolongation can be increased when Ajmaline is combined with Dexchlorpheniramine. Alfuzosin The risk or severity of QTc prolongation can be increased when Alfuzosin is combined with Dexchlorpheniramine. Alimemazine The risk or severity of QTc prolongation can be increased when Alimemazine is combined with Dexchlorpheniramine. 
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- Not Available
Products
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Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Dextromethorphan Tannate, Phenylephrine Tannate, Dexchlorpheniramine Tannate Dexchlorpheniramine (2 mg/5mL) + Dextromethorphan (30 mg/5mL) + Phenylephrine (20 mg/5mL) Suspension Oral River's Edge Pharmaceuticals, LLC 2008-08-01 2010-07-31 US 
Categories
- ATC Codes
- R06AB52 — Dexchlorpheniramine, combinations
- R06AB — Substituted alkylamines
- R06A — ANTIHISTAMINES FOR SYSTEMIC USE
- R06 — ANTIHISTAMINES FOR SYSTEMIC USE
- R — RESPIRATORY SYSTEM
- Drug Categories
- Agents that reduce seizure threshold
- Antihistamines for Systemic Use
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Histamine Agents
- Histamine Antagonists
- Histamine H1 Antagonists
- Moderate Risk QTc-Prolonging Agents
- Neurotransmitter Agents
- Pyridines
- QTc Prolonging Agents
- Stereoisomerism
- Substituted Alkylamines
- 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
- External Links
- Human Metabolome Database
- HMDB0240218
- KEGG Compound
- C06946
- PubChem Compound
- 33036
- PubChem Substance
- 347829309
- ChemSpider
- 30576
- 22697
- ChEBI
- 4464
- ChEMBL
- CHEMBL1201353
- ZINC
- ZINC000000113404
- Wikipedia
- Dexchlorpheniramine
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Prostate Cancer 1 3 Active Not Recruiting Treatment Disseminated Sclerosis 1 3 Completed Prevention Hemodynamics Instability / Vasoplegic Syndrome 1 3 Completed Treatment Allergic Rhinitis (AR) 1 3 Not Yet Recruiting Treatment Nephritis, Lupus / Systemic Lupus Erythematosus (SLE) 1 3 Terminated Treatment Cutaneous Hypersensitivity 1 3 Unknown Status Treatment Allergic Rhinitis (AR) 1 3 Unknown Status Treatment Insect Bites 2 3 Unknown Status Treatment Sunburn 2 3 Unknown Status Treatment Viral Infections of the Upper Respiratory Tract 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Solution Oral Suspension Oral Syrup Oral Syrup Oral Tablet Oral Syrup Oral 0.04 g Tablet Oral 3 mg Tablet Oral 2 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0519 mg/mL ALOGPS logP 3.74 ALOGPS logP 3.58 ChemAxon logS -3.7 ALOGPS pKa (Strongest Basic) 9.47 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 16.13 Å2 ChemAxon Rotatable Bond Count 5 ChemAxon Refractivity 80.85 m3·mol-1 ChemAxon Polarizability 30.82 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available LC-MS/MS Spectrum - LC-ESI-qTof , Positive LC-MS/MS Not Available MS/MS Spectrum - , positive LC-MS/MS splash10-001i-0190000000-f6ef5e736260c9c22a16 MS/MS Spectrum - , positive LC-MS/MS splash10-0uy0-0960000000-24a36e80af50293ed70d
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- 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
- 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]
- 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