Dexbrompheniramine is an antihistamine used to treat allergy symptoms including upper respiratory tract symptoms.
- Brand Names
- Ala-hist Ir, Ala-hist PE, Dologen, Dologesic Reformulated Jun 2016
- Generic Name
- DrugBank Accession Number
Dexbrompheniramine maleate is an antihistamine agent that is used for the treatment of allergic conditions, such as hay fever or urticaria.
- Small Molecule
- Average: 319.239
- Chemical Formula
- 3-(4-bromophenyl)- N,N-dimethyl- 3-pyridin-2-yl-propan-1-amine
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- Associated Conditions
- Contraindications & Blackbox Warnings
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In allergic reactions an allergen interacts with and cross-links surface IgE antibodies on mast cells and basophils. Once the mast cell-antibody-antigen complex is formed, a complex series of events occurs that eventually leads to cell-degranulation and the release of histamine (and other chemical mediators) from the mast cell or basophil. Once released, 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. Dexbrompheniramine is a histamine H1 antagonist (or more correctly, an inverse histamine agonist) of the alkylamine class. 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
Dexbrompheniramine competitively binds to the histamine H1-receptor. It competes with histamine for the normal H1-receptor sites on effector cells of the gastrointestinal tract, blood vessels and respiratory tract. This blocks the action of endogenous histamine, which subsequently leads to temporary relief of the negative symptoms brought on by histamine.
Target Actions Organism AHistamine H1 receptorantagonist Humans
Antihistamines are well absorbed from the gastrointestinal tract after oral administration.
- Volume of distribution
- Protein binding
Hepatic (cytochrome P-450 system), some renal.
- Route of elimination
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.
Signs of an overdose include fast or irregular heartbeat, mental or mood changes, tightness in the chest, and unusual tiredness or weakness.
Pathway Category Dexbrompheniramine H1-Antihistamine Action Drug action
- Pharmacogenomic Effects/ADRs
- Not Available
- 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 1,2-Benzodiazepine The risk or severity of adverse effects can be increased when Dexbrompheniramine is combined with 1,2-Benzodiazepine. Acetazolamide The risk or severity of adverse effects can be increased when Dexbrompheniramine is combined with Acetazolamide. Acetophenazine The risk or severity of adverse effects can be increased when Dexbrompheniramine is combined with Acetophenazine. Aclidinium Dexbrompheniramine may increase the central nervous system depressant (CNS depressant) activities of Aclidinium. Acrivastine The risk or severity of QTc prolongation can be increased when Dexbrompheniramine is combined with Acrivastine. Adenosine The risk or severity of QTc prolongation can be increased when Dexbrompheniramine is combined with Adenosine. Agomelatine The risk or severity of adverse effects can be increased when Dexbrompheniramine is combined with Agomelatine. Ajmaline The risk or severity of QTc prolongation can be increased when Dexbrompheniramine is combined with Ajmaline. Alfentanil The risk or severity of adverse effects can be increased when Dexbrompheniramine is combined with Alfentanil. Alfuzosin The risk or severity of QTc prolongation can be increased when Alfuzosin is combined with Dexbrompheniramine.Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more
- Food Interactions
- Avoid alcohol. Taking with alcohol may increase drowsiness.
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Dexbrompheniramine maleate BPA9UT29BS 2391-03-9 SRGKFVAASLQVBO-DASCVMRKSA-N
- International/Other Brands
- Disophrol (Schering) / Drixoral (Schering )
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ala-hist Ir Tablet 2 mg/1 Oral Poly Pharmaceuticals, Inc. 2011-08-22 Not applicable PediaVent Tablet, chewable 1 mg/1 Oral Carwin Associates, Inc 2014-08-05 Not applicable PediaVent Syrup 2 mg/5mL Oral Carwin Associates, Inc 2014-08-04 Not applicable
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Acticon Dexbrompheniramine maleate (2 mg/1) + Pseudoephedrine hydrochloride (60 mg/1) Tablet Oral Actipharma, Inc 2015-08-13 Not applicable Acticon Dexbrompheniramine maleate (1 mg/5mL) + Pseudoephedrine hydrochloride (30 mg/5mL) Liquid Oral ACTIPHARMA, INC. 2016-07-14 Not applicable Actidogesic Dexbrompheniramine maleate (1 mg/1) + Acetaminophen (500 mg/1) Tablet Oral Actipharma, Inc 2016-10-14 Not applicable Actidogesic DF Dexbrompheniramine maleate (1 mg/1) + Acetaminophen (500 mg/1) Tablet Oral Actipharma, Inc 2020-07-10 Not applicable Ala-hist PE Dexbrompheniramine maleate (2 mg/1) + Phenylephrine hydrochloride (10 mg/1) Tablet Oral Poly Pharmaceuticals, Inc. 2011-09-15 Not applicable Alahist CF Dexbrompheniramine maleate (2 g/1) + Dextromethorphan hydrobromide monohydrate (20 g/1) + Phenylephrine hydrochloride (10 g/1) Tablet Oral Poly Pharmaceuticals, Inc. 2017-09-14 Not applicable Alahist DM Dexbrompheniramine maleate (2 mg/5mL) + Dextromethorphan hydrobromide monohydrate (15 mg/5mL) + Phenylephrine hydrochloride (7.5 mg/5mL) Liquid Oral Poly Pharmaceuticals, Inc. 2016-09-01 Not applicable Alahist PE Dexbrompheniramine maleate (2 mg/1) + Phenylephrine hydrochloride (7.5 mg/1) Tablet Oral Poly Pharmaceuticals, Inc. 2020-08-24 Not applicable Bio-cnex Dexbrompheniramine maleate (1 mg/5mL) + Pseudoephedrine hydrochloride (30 mg/5mL) Liquid Oral Advanced Generic Corporation 2017-01-01 Not applicable Biogesic Dexbrompheniramine maleate (1 mg/1) + Acetaminophen (500 mg/1) Tablet Oral Advanced Generic Corporation 2017-01-01 Not applicable
- Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Brompheniramine Maleate Pseudoephedrine HCl Dexbrompheniramine maleate (1 mg/1mL) + Pseudoephedrine hydrochloride (7.5 mg/1mL) Liquid Oral River's Edge Pharmaceuticals, LLC 2008-06-01 2010-10-31
- ATC Codes
- R06AB06 — Dexbrompheniramine
- R06AB — Substituted alkylamines
- R06A — ANTIHISTAMINES FOR SYSTEMIC USE
- R06 — ANTIHISTAMINES FOR SYSTEMIC USE
- R — RESPIRATORY SYSTEM
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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.
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Pyridines and derivatives
- Sub Class
- Direct Parent
- Alternative Parents
- Bromobenzenes / Aralkylamines / Aryl bromides / Heteroaromatic compounds / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Organobromides / Hydrocarbon derivatives
- Amine / Aralkylamine / Aromatic heteromonocyclic compound / Aryl bromide / Aryl halide / Azacycle / Benzenoid / Bromobenzene / Halobenzene / Heteroaromatic compound
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- brompheniramine (CHEBI:59269)
- Affected organisms
- Humans and other mammals
- CAS number
- InChI Key
- IUPAC Name
- Synthesis Reference
Walter, L.A.; U.S. Patents 3,061,517; October 30, 1962; and 3,030,371; April 17, 1962; both assigned to Schering Corporation.
- General References
- Not Available
- Schering corp sub schering plough corp
- Poly Pharmaceuticals Inc.
- Dosage Forms
Form Route Strength Tablet Oral 2 mg/1 Liquid Oral Tablet, extended release Oral Tablet Oral Tablet; tablet, extended release Oral Syrup Oral 2 mg/5mL Tablet, chewable Oral 1 mg/1 Syrup Oral
Unit description Cost Unit Ala-hist ir 2 mg tablet 0.82USD tabletDrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
- Not Available
- Experimental Properties
Property Value Source melting point (°C) 113-115 US. Patent 3,030,371. logP 3.4 Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0127 mg/mL ALOGPS logP 3.63 ALOGPS logP 3.75 ChemAxon logS -4.4 ALOGPS pKa (Strongest Basic) 9.48 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 83.67 m3·mol-1 ChemAxon Polarizability 31.84 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
Property Value Probability Human Intestinal Absorption + 0.9648 Blood Brain Barrier + 0.9576 Caco-2 permeable + 0.8867 P-glycoprotein substrate Substrate 0.6242 P-glycoprotein inhibitor I Non-inhibitor 0.8782 P-glycoprotein inhibitor II Non-inhibitor 0.93 Renal organic cation transporter Inhibitor 0.7955 CYP450 2C9 substrate Non-substrate 0.8345 CYP450 2D6 substrate Substrate 0.8346 CYP450 3A4 substrate Substrate 0.5898 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Inhibitor 0.8932 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.8398 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7748 Ames test Non AMES toxic 0.9351 Carcinogenicity Non-carcinogens 0.9349 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 3.0758 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9121 hERG inhibition (predictor II) Inhibitor 0.7207
- Mass Spec (NIST)
- Not Available
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 splash10-0292-0940000000-f369442eba5344b3ecb4
- Pharmacological action
- 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
- Uniprot ID
- Uniprot Name
- Histamine H1 receptor
- Molecular Weight
- 55783.61 Da
- McLeod RL, Mingo G, O'Reilly S, Ruck LA, Bolser DC, Hey JA: Antitussive action of antihistamines is independent of sedative and ventilation activity in the guinea pig. Pharmacology. 1998 Aug;57(2):57-64. [Article]
- Bokesoy TA, Onaran HO: Atypical Schild plots with histamine H1 receptor agonists and antagonists in the rabbit aorta. Eur J Pharmacol. 1991 May 2;197(1):49-56. [Article]
- Onaran HO, Bokesoy TA: Kinetics of antagonism at histamine-H1 receptors in isolated rabbit arteries. Naunyn Schmiedebergs Arch Pharmacol. 1990 Apr;341(4):316-23. [Article]
- Yanni JM, Stephens DJ, Parnell DW, Spellman JM: Preclinical efficacy of emedastine, a potent, selective histamine H1 antagonist for topical ocular use. J Ocul Pharmacol. 1994 Winter;10(4):665-75. [Article]
- Sadofsky LR, Campi B, Trevisani M, Compton SJ, Morice AH: Transient receptor potential vanilloid-1-mediated calcium responses are inhibited by the alkylamine antihistamines dexbrompheniramine and chlorpheniramine. Exp Lung Res. 2008 Dec;34(10):681-93. doi: 10.1080/01902140802339623. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Drug created on June 13, 2005 13:24 / Updated on July 03, 2021 09:04