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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyDexbrompheniramine
Identification
- Name
- Dexbrompheniramine
- Accession Number
- DB00405 (APRD00770)
- Type
- Small Molecule
- Groups
- Approved
- Description
Dexbrompheniramine maleate is an antihistamine used to treat allergic conditions such as hay fever or urticaria.
- Structure
Structure for Dexbrompheniramine (DB00405)
- Synonyms
- (+)-brompheniraminum
- (R)-3-(4-Bromophenyl)-3-(2-pyridyl)propyldimethylamine
- (S)-(+)-brompheniramine
- (S)-brompheniramine
- 3-(4-bromophenyl)- N,N-dimethyl- 3-pyridin-2-yl-propan-1-amine
- d-brompheniramine
- Desbrofeniramina
- Dexbromfeniramina
- Dexbrompheniramin
- Dexbromphéniramine
- Dexbrompheniramine
- Dexbrompheniraminum
- Product Ingredients
Ingredient UNII CAS InChI Key Dexbrompheniramine maleate BPA9UT29BS 2391-03-9 SRGKFVAASLQVBO-DASCVMRKSA-N - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Ala-hist Ir Tablet 2 mg/1 Oral Poly Pharmaceuticals 2011-08-22 Not applicable US 
PediaVent Syrup 2 mg/5mL Oral Carwin Associates, Inc 2014-08-04 Not applicable US PediaVent Tablet, chewable 1 mg/1 Oral Carwin Associates, Inc 2014-08-05 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Acticon Dexbrompheniramine maleate (1 mg/5mL) + Pseudoephedrine hydrochloride (30 mg/5mL) Liquid Oral ACTIPHARMA, INC. 2016-07-14 Not applicable US Acticon Dexbrompheniramine maleate (2 mg/1) + Pseudoephedrine hydrochloride (60 mg/1) Tablet Oral Actipharma, Inc 2015-08-13 Not applicable US Actidogesic Dexbrompheniramine maleate (1 mg/1) + Acetaminophen (500 mg/1) Tablet Oral Actipharma, Inc 2016-10-14 Not applicable US Ala-hist PE Dexbrompheniramine maleate (2 mg/1) + Phenylephrine hydrochloride (10 mg/1) Tablet Oral Poly Pharmaceuticals 2011-09-15 Not applicable US Alahist CF Dexbrompheniramine maleate (2 g/1) + Dextromethorphan hydrobromide monohydrate (20 g/1) + Phenylephrine hydrochloride (10 g/1) Tablet Oral Poly Pharmaceuticals 2017-09-14 Not applicable US Alahistdm DM Dexbrompheniramine maleate (2 mg/5mL) + Dextromethorphan hydrobromide monohydrate (15 mg/5mL) + Phenylephrine hydrochloride (7.5 mg/5mL) Liquid Oral Poly Pharmaceuticals 2016-09-01 Not applicable US Bio-cnex Dexbrompheniramine maleate (1 mg/5mL) + Pseudoephedrine hydrochloride (30 mg/5mL) Liquid Oral Advanced Generic Corporation 2017-01-01 Not applicable US Biogesic Dexbrompheniramine maleate (1 mg/1) + Acetaminophen (500 mg/1) Tablet Oral Advanced Generic Corporation 2017-01-01 Not applicable US Bionatuss DXP Dexbrompheniramine maleate (2 mg/5mL) + Dextromethorphan hydrobromide monohydrate (20 mg/5mL) + Phenylephrine hydrochloride (10 mg/5mL) Liquid Oral Advanced Generic Corporation 2009-10-01 Not applicable US Chlo Hist Dexbrompheniramine maleate (1 mg/5mL) + Chlophedianol hydrochloride (12.5 mg/5mL) Liquid Oral R. A. McNeil Company 2014-09-15 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End 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 US - International/Other Brands
- Disophrol (Schering) / Drixoral (Schering )
- Categories
- UNII
- 75T64B71RP
- CAS number
- 132-21-8
- Weight
- Average: 319.239
Monoisotopic: 318.073161265 - Chemical Formula
- C16H19BrN2
- InChI Key
- ZDIGNSYAACHWNL-HNNXBMFYSA-N
- InChI
- InChI=1S/C16H19BrN2/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-bromophenyl)-3-(pyridin-2-yl)propyl]dimethylamine
- SMILES
- CN(C)CC[C@@H](C1=CC=C(Br)C=C1)C1=CC=CC=N1
Pharmacology
- Indication
For treatment and relief of symptoms of allergies, hay fever, and colds
- Associated Conditions
- Pharmacodynamics
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 receptor antagonistHumans - Absorption
Antihistamines are well absorbed from the gastrointestinal tract after oral administration.
- Volume of distribution
- Not Available
- Protein binding
- Not Available
- Metabolism
Hepatic (cytochrome P-450 system), some renal.
- Route of elimination
- Not Available
- Half life
25 hours
- Clearance
- Not Available
- Toxicity
Signs of an overdose include fast or irregular heartbeat, mental or mood changes, tightness in the chest, and unusual tiredness or weakness.
- Affected organisms
- Humans and other mammals
- Pathways
Pathway Category Dexbrompheniramine H1-Antihistamine Action Drug action - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
Drug Interaction 2,5-Dimethoxy-4-ethylamphetamine 2,5-Dimethoxy-4-ethylamphetamine may decrease the sedative and stimulatory activities of Dexbrompheniramine. 2,5-Dimethoxy-4-ethylthioamphetamine 2,5-Dimethoxy-4-ethylthioamphetamine may decrease the sedative and stimulatory activities of Dexbrompheniramine. 3,4-Methylenedioxyamphetamine 3,4-Methylenedioxyamphetamine may decrease the sedative and stimulatory activities of Dexbrompheniramine. 4-Bromo-2,5-dimethoxyamphetamine 4-Bromo-2,5-dimethoxyamphetamine may decrease the sedative and stimulatory activities of Dexbrompheniramine. 4-Methoxyamphetamine The risk or severity of adverse effects can be increased when Dexbrompheniramine is combined with 4-Methoxyamphetamine. 7-Nitroindazole The risk or severity of adverse effects can be increased when Dexbrompheniramine is combined with 7-Nitroindazole. Abexinostat The risk or severity of QTc prolongation can be increased when Dexbrompheniramine is combined with Abexinostat. Acebutolol The risk or severity of QTc prolongation can be increased when Dexbrompheniramine is combined with Acebutolol. Acepromazine The risk or severity of adverse effects can be increased when Dexbrompheniramine is combined with Acepromazine. Aceprometazine The risk or severity of adverse effects can be increased when Dexbrompheniramine is combined with Aceprometazine. - Food Interactions
- Not Available
References
- 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
- External Links
- Human Metabolome Database
- HMDB0014549
- PubChem Compound
- 16960
- PubChem Substance
- 46505186
- ChemSpider
- 16068
- ChEBI
- 59269
- ChEMBL
- CHEMBL1201287
- Therapeutic Targets Database
- DAP001068
- PharmGKB
- PA164746251
- Wikipedia
- Dexbrompheniramine
- ATC Codes
- R06AB06 — Dexbrompheniramine
- R06AB — Substituted alkylamines
- R06A — ANTIHISTAMINES FOR SYSTEMIC USE
- R06 — ANTIHISTAMINES FOR SYSTEMIC USE
- R — RESPIRATORY SYSTEM
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Schering corp sub schering plough corp
- Packagers
- Poly Pharmaceuticals Inc.
- Dosage forms
Form Route Strength Tablet Oral 2 mg/1 Liquid Oral Tablet, extended release Oral Tablet; tablet, extended release Oral Syrup Oral Tablet Oral Syrup Oral 2 mg/5mL Tablet, chewable Oral 1 mg/1 - Prices
Unit description Cost Unit Ala-hist ir 2 mg tablet 0.82USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- 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
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 splash10-0292-0940000000-f369442eba5344b3ecb4
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
- Bromobenzenes / Aralkylamines / Aryl bromides / Heteroaromatic compounds / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Organobromides / Hydrocarbon derivatives
- Substituents
- Pheniramine / Bromobenzene / Halobenzene / Aralkylamine / Aryl bromide / Benzenoid / Monocyclic benzene moiety / Aryl halide / Heteroaromatic compound / Tertiary aliphatic amine
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- brompheniramine (CHEBI:59269)
Targets
- Kind
- Protein
- Organism
- Humans
- 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
References
- 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. [PubMed:9691225]
- 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. [PubMed:1680053]
- 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. [PubMed:1970615]
- 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. [PubMed:7714410]
- 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. [PubMed:19085565]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Drug created on June 13, 2005 07:24 / Updated on February 20, 2019 19:19