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Showing drug card for Brompheniramine (DB00835)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-04-16 16:48:02
Primary Accession Number DB00835
Secondary Accession Number
  • APRD00832
Name Brompheniramine
Drug Type
  • Approved
  • Small Molecule
Description Histamine H1 antagonist used in treatment of allergies, rhinitis, and urticaria. [PubChem]
Synonyms
  1. Brompheniramine Maleate
Brand Names
  1. Bromfed
  2. Bromfenex
  3. Dimetane
  4. Veltane
Brand Mixtures
  1. Cold & Allergy (Brompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride)
  2. Cold & Allergy Relief - Liq (Brompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride)
  3. Cold Relief (Brompheniramine Maleate + Phenylpropanolamine Hydrochloride)
  4. Cold Relief Dm (Brompheniramine Maleate + Dextromethorphan Hydrobromide + Phenylpropanolamine Hydrochloride)
  5. Cough, Cold & Allergy Relief (Brompheniramine Maleate + Dextromethorphan Hydrobromide + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride)
  6. Decongestant Antihistaminic Syrup (Brompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride)
  7. Dimetane Expectorant Liq (Brompheniramine Maleate + Guaifenesin + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride)
  8. Dimetane Expectorant-C Syr (Brompheniramine Maleate + Codeine Phosphate + Guaifenesin + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride)
  9. Dimetane Expectorant-C Syrup (Brompheniramine Maleate + Codeine Phosphate + Guaifenesin + Phenylephrine Hydrochloride)
  10. Dimetane Expectorant-Dc Syr (Brompheniramine Maleate + Guaifenesin + Hydrocodone Bitartrate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride)
  11. Dimetane Expectorant-Dc Syrup (Brompheniramine Maleate + Guaifenesin + Hydrocodone Bitartrate + Phenylephrine Hydrochloride)
  12. Dimetapp (Brompheniramine Maleate + Phenylephrine Hydrochloride)
  13. Dimetapp Chewable Tablets (Brompheniramine Maleate + Phenylpropanolamine Hydrochloride)
  14. Dimetapp Children's Cold & Allergy Tablets (Brompheniramine Maleate + Phenylpropanolamine Hydrochloride)
  15. Dimetapp Children's Cold & Fever (Acetaminophen + Brompheniramine Maleate + Phenylpropanolamine Hydrochloride)
  16. Dimetapp Clear (Brompheniramine Maleate + Phenylpropanolamine Hydrochloride)
  17. Dimetapp Cough & Cold Liqui-Gels - Cap (Brompheniramine Maleate + Dextromethorphan Hydrobromide + Phenylpropanolamine Hydrochloride)
  18. Dimetapp Cough, Cold & Flu (Acetaminophen + Brompheniramine Maleate + Dextromethorphan Hydrobromide + Phenylpropanolamine Hydrochloride)
  19. Dimetapp Dm Cough & Cold Liquid (Brompheniramine Maleate + Dextromethorphan Hydrobromide + Phenylephrine Hydrochloride)
  20. Dimetapp Dm Elixir (Brompheniramine Maleate + Dextromethorphan Hydrobromide + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride)
  21. Dimetapp Dm Tab (Brompheniramine Maleate + Dextromethorphan Hydrobromide + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride)
  22. Dimetapp Elixir (Brompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride)
  23. Dimetapp Extentabs (Brompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride)
  24. Dimetapp Extra Strength (Brompheniramine Maleate + Phenylephrine Hydrochloride)
  25. Dimetapp Extra Strength Dm Cough & Cold (Brompheniramine Maleate + Dextromethorphan Hydrobromide + Phenylephrine Hydrochloride)
  26. Dimetapp Liqui-Gels Cap (Brompheniramine Maleate + Phenylpropanolamine Hydrochloride)
  27. Dimetapp Oral Infant Cold Drops (Brompheniramine Maleate + Phenylephrine Hydrochloride)
  28. Dimetapp Oral Infant Cold and Fever Drops (Acetaminophen + Brompheniramine Maleate + Phenylephrine Hydrochloride)
  29. Dimetapp Oral Infant Drops (Brompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride)
  30. Dimetapp Tab (Brompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride)
  31. Dimetapp-C Syr (Brompheniramine Maleate + Codeine Phosphate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride)
  32. Dimetapp-C Syrup (Brompheniramine Maleate + Codeine Phosphate + Phenylephrine Hydrochloride)
  33. Pharmetapp Elixir (Brompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride)
  34. Tantapp Elixir (Brompheniramine Maleate + Phenylephrine Hydrochloride + Phenylpropanolamine Hydrochloride)
Chemical IUPAC Name 3-(4-bromophenyl)-N,N-dimethyl-3-pyridin-2-ylpropan-1-amine
Chemical Formula C16H19BrN2
Chemical Structure Structure
CAS Registry Number 86-22-6
InChI Identifier InChI=1/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
InChI Key ZDIGNSYAACHWNL-UHFFFAOYAT
KEGG Drug Not Available
KEGG Compound C06857 Link Image
PubChem Compound 6834 Link Image
PubChem Substance 9075 Link Image
ChEBI ID Not Available
PharmGKB ID PA448675 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] 02244079 Link Image
RxList Link Not Available
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Brompheniramine Link Image
FDA Label Not Available
Material Safety Data Sheet (MSDS)
Synthesis Reference Not Available
Average Molecular Weight 319.2390
Monoisotopic Molecular Weight 318.0732
State Liquid
Melting Point < 25 oC
Experimental Water Solubility Freely soluble (maleate salt) Source: PhysProp
Predicted Water Solubility 1.27e-02 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 3.4 Source: PhysProp
Predicted LogP 3.63 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -4.40 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES CN(C)CC[C@H](C1=CC=C(Br)C=C1)C1=CC=CC=N1
Canonical SMILES CN(C)CCC(C1=CC=C(Br)C=C1)C1=CC=CC=N1
Drug Category
  • Anti-Allergic Agents
  • Histamine H1 Antagonists
ATC Codes
AHFS Codes Not Available
Indication For the treatment of the symptoms of the common cold and allergic rhinitis, such as runny nose, itchy eyes, watery eyes, and sneezing.
Pharmacology Brompheniramine is an antihistaminergic medication of the propylamine class. It is a first-generation antihistamine. 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. Brompheniramine 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 Brompheniramine works by acting as an antagonist of the H1 histamine receptors. It also functions as a moderately effective anticholingeric agent, likely an antimuscarinic agent similar to other common antihistamines such as diphenhydramine. Its effects on the cholinergic system may include side-effects such as drowsiness, sedation, dry mouth, dry throat, blurred vision, and increased heart rate.
Absorption Antihistamines are well absorbed from the gastrointestinal tract after oral administration.
Toxicity Oral, rat: LD50 = 318 mg/kg. Signs of overdose include fast or irregular heartbeat, mental or mood changes, tightness in the chest, and unusual tiredness or weakness.
Protein Binding Not Available
Biotransformation Hepatic (cytochrome P-450 system), some renal.
Half Life Not Available
Dosage Forms Not Available
Patient Information Show Link Image
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions
Drug Interaction
Donepezil Possible antagonism of action
Galantamine Possible antagonism of action
Rivastigmine Possible antagonism of action
Food Interactions
  • Avoid alcohol.
  • Take with food.
Pathways Not Available
General References
  1. Drugs.com Link Image
  2. Wikipedia Link Image
Organisms Affected
  • Humans and other mammals
Targets
  1. Histamine H1 receptor
Drug Target 1 [top]
Target 1 ID 492
Target 1 Name Histamine H1 receptor
Target 1 Synonyms Not Available
Target 1 Gene Name HRH1
Target 1 Protein Sequence >Histamine H1 receptor 
MSLPNSSCLLEDKMCEGNKTTMASPQLMPLVVVLSTICLVTVGLNLLVLYAVRSERKLHT
VGNLYIVSLSVADLIVGAVVMPMNILYLLMSKWSLGRPLCLFWLSMDYVASTASIFSVFI
LCIDRYRSVQQPLRYLKYRTKTRASATILGAWFLSFLWVIPILGWNHFMQQTSVRREDKC
ETDFYDVTWFKVMTAIINFYLPTLLMLWFYAKIYKAVRQHCQHRELINRSLPSFSEIKLR
PENPKGDAKKPGKESPWEVLKRKPKDAGGGSVLKSPSQTPKEMKSPVVFSQEDDREVDKL
YCFPLDIVHMQAAAEGSSRDYVAVNRSHGQLKTDEQGLNTHGASEISEDQMLGDSQSFSR
TDSDTTTETAPGKGKLRSGSNTGLDYIKFTWKRLRSHSRQYVSGLHMNRERKAAKQLGFI
MAAFILCWIPYFIFFMVIAFCKNCCNEHLHMFTIWLGYINSTLNPLIYPLCNENFKKTFK
RILHIRS
Target 1 Number of Residues 495
Target 1 Molecular Weight 55785
Target 1 Theoretical pI 9.58
Target 1 GO Classification
Function
amine receptor activity
histamine receptor activity
signal transducer activity
receptor activity
transmembrane receptor activity
G-protein coupled receptor activity
rhodopsin-like receptor activity
Process
cellular process
cell communication
signal transduction
cell surface receptor linked signal transduction
G-protein coupled receptor protein signaling pathway
Component
cell
membrane
intrinsic to membrane
integral to membrane
Target 1 General Function Involved in rhodopsin-like receptor activity
Target 1 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 catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • 30-49
  • 64-83
  • 102-123
  • 146-165
  • 190-210
  • 419-438
  • 451-470
Target 1 Essentiality Non-Essential
Target 1 GenBank ID Protein 510296 Link Image
Target 1 UniProtKB/Swiss-Prot ID P35367 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name HRH1_HUMAN Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location
  • Membrane
  • multi-pass membrane protein
Target 1 Gene Sequence >1464 bp 
ATGAGCCTCCCCAATTCCTCCTGCCTCTTAGAAGACAAGATGTGTGAGGGCAACAAGACC
ACTATGGCCAGCCCCCAGCTGATGCCCCTGGTGGTGGTCCTGAGCACTATCTGCTTGGTC
ACAGTAGGGCTCAACCTGCTGGTGCTGTATGCCGTACGGAGTGAGCGGAAGCTCCACACT
GTGGGGAACCTGTACATCGTCAGCCTCTCGGTGGCGGACTTGATCGTGGGTGCCGTCGTC
ATGCCTATGAACATCCTCTACCTGCTCATGTCCAAGTGGTCACTGGGCCGTCCTCTCTGC
CTCTTTTGGCTTTCCATGGACTATGTGGCCAGCACAGCGTCCATTTTCAGTGTCTTCATC
CTGTGCATTGATCGCTACCGCTCTGTCCAGCAGCCCCTCAGGTACCTTAAGTATCGTACC
AAGACCCGAGCCTCGGCCACCATTCTGGGGGCCTGGTTTCTCTCTTTTCTGTGGGTTATT
CCCATTCTAGGCTGGAATCACTTCATGCAGCAGACCTCGGTGCGCCGAGAGGACAAGTGT
GAGACAGACTTCTATGATGTCACCTGGTTCAAGGTCATGACTGCCATCATCAACTTCTAC
CTGCCCACCTTGCTCATGCTCTGGTTCTATGCCAAGATCTACAAGGCCGTACGACAACAC
TGCCAGCACCGGGAGCTCATCAATAGGTCCCTCCCTTCCTTCTCAGAAATTAAGCTGAGG
CCAGAGAACCCCAAGGGGGATGCCAAGAAACCAGGGAAGGAGTCTCCCTGGGAGGTTCTG
AAAAGGAAGCCAAAAGATGCTGGTGGTGGATCTGTCTTGAAGTCACCATCCCAAACCCCC
AAGGAGATGAAATCCCCAGTTGTCTTCAGCCAAGAGGATGATAGAGAAGTAGACAAACTC
TACTGCTTTCCACTTGATATTGTGCACATGCAGGCTGCGGCAGAGGGGAGTAGCAGGGAC
TATGTAGCCGTCAACCGGAGCCATGGCCAGCTCAAGACAGATGAGCAGGGCCTGAACACA
CATGGGGCCAGCGAGATATCAGAGGATCAGATGTTAGGTGATAGCCAATCCTTCTCTCGA
ACGGACTCAGATACCACCACAGAGACAGCACCAGGCAAAGGCAAATTGAGGAGTGGGTCT
AACACAGGCCTGGATTACATCAAGTTTACTTGGAAGAGGCTCCGCTCGCATTCAAGACAG
TATGTATCTGGGTTGCACATGAACCGCGAAAGGAAGGCCGCCAAACAGTTGGGTTTTATC
ATGGCAGCCTTCATCCTCTGCTGGATCCCTTATTTCATCTTCTTCATGGTCATTGCCTTC
TGCAAGAACTGTTGCAATGAACATTTGCACATGTTCACCATCTGGCTGGGCTACATCAAC
TCCACACTGAACCCCCTCATCTACCCCTTGTGCAATGAGAACTTCAAGAAGACATTCAAG
AGAATTCTGCATATTCGCTCCTAA
Target 1 GenBank Gene ID
Target 1 GeneCard ID HRH1 Link Image
Target 1 GenAtlas ID HRH1 Link Image
Target 1 HGNC ID HGNC:5182 Link Image
Target 1 Chromosome Location 3
Target 1 Locus 3p25
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Fukui H, Fujimoto K, Mizuguchi H, Sakamoto K, Horio Y, Takai S, Yamada K, Ito S: Molecular cloning of the human histamine H1 receptor gene. Biochem Biophys Res Commun. 1994 Jun 15;201(2):894-901. [PubMed Link Image]
  2. De Backer MD, Gommeren W, Moereels H, Nobels G, Van Gompel P, Leysen JE, Luyten WH: Genomic cloning, heterologous expression and pharmacological characterization of a human histamine H1 receptor. Biochem Biophys Res Commun. 1993 Dec 30;197(3):1601-8. [PubMed Link Image]
Target 1 Drug References
  1. 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 Link Image]
  2. 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 Link Image]
  3. 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 Link Image]

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.