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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 Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • D-Brompheniramine
  • Parabromdylamine
  • Parabromodylamine
Synonyms
D-Brompheniramine
Parabromdylamine
Parabromodylamine
Salts Not Available
Brand names
Name Company
Ilvin
Brand mixtures
Brand Name Ingredients
Drixoral Cold & Sinus Dexbrompheniramine Maleate + Pseudoephedrine Sulfate
Drixoral Day/Night - Srt/Tabs Dexbrompheniramine Maleate + Pseudoephedrine Sulfate
Drixoral Syrup Dexbrompheniramine Maleate + Pseudoephedrine Sulfate
Drixtab Tab Dexbrompheniramine Maleate + Pseudoephedrine Sulfate
Categories
  • Antihistamines
CAS number 132-21-8
Weight Average: 319.239
Monoisotopic: 318.073161265
Chemical Formula C16H19BrN2
InChI Key InChIKey=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
Plain Text
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
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Pheniramines
Substructures
  • Pheniramines
  • Pyridines and Derivatives
  • Benzene and Derivatives
  • Aliphatic and Aryl Amines
  • Aryl Halides
  • Heterocyclic compounds
  • Aromatic compounds
  • Phenylpropylamines
  • Imines
  • Halobenzenes
Pharmacology
Indication For treatment and relief of symptoms of allergies, hay fever, and colds
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.
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 Not Available
Pharmacoeconomics
Manufacturers
  • Schering corp sub schering plough corp
Packagers
Dosage forms Not Available
Prices
Unit description Cost Unit
Ala-hist ir 2 mg tablet 0.82 USD tablet
Patents Not Available
Properties
State solid
Melting point Not Available
Experimental Properties
Property Value Source
logP 3.4 PhysProp
Predicted Properties
Property Value Source
water solubility 1.27e-02 g/l ALOGPS
logP 3.63 ALOGPS
logP 3.75 ChemAxon Molconvert
logS -4.4 ALOGPS
pKa 0 ChemAxon Molconvert
hydrogen acceptor count 2 ChemAxon Molconvert
hydrogen donor count 0 ChemAxon Molconvert
polar surface area 16.13 ChemAxon Molconvert
rotatable bond count 5 ChemAxon Molconvert
refractivity 83.67 ChemAxon Molconvert
polarizability 31.84 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
PubChem Compound 16960 Link_out
PubChem Substance 46505186 Link_out
ChemSpider 16068 Link_out
ChEBI 59269 Link_out
ChEMBL 59269 Link_out
Therapeutic Targets Database DAP001068 Link_out
PharmGKB PA449250 Link_out
Drug Product Database 411892 Link_out
Wikipedia http://en.wikipedia.org/wiki/Dexbrompheniramine Link_out
ATC Codes
  • R06AB06
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions
Drug Interaction
Donepezil Possible antagonism of action
Galantamine Possible antagonism of action
Tacrine The therapeutic effects of the central acetylcholinesterase inhibitor, Tacrine, and/or the anticholinergic, Dexbrompheniramine, may be reduced due to antagonism. The interaction may be beneficial when the anticholinergic action is a side effect. Monitor for decreased efficacy of both agents.
Trimethobenzamide Trimethobenzamide and Dexbrompheniramine, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Triprolidine Triprolidine and Dexbrompheniramine, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Additive CNS depressant effects may also occur. Monitor for enhanced anticholinergic and CNS depressant effects.
Trospium Trospium and Dexbrompheniramine, two anticholinergics, may cause additive anticholinergic effects and enhanced adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Food Interactions Not Available
Targets

1. Histamine H1 receptor

Pharmacological action: yes
Actions: antagonist

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 catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system

Organism class: human
UniProt ID: P35367 Link_out
Gene: HRH1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. 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
  2. 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
  3. 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
  4. 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# 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. Pubmed
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 14, 2012 11:41