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targets (1) transporters (2)
for drugs
Identification
Name Bromodiphenhydramine
Accession Number DB01237 (APRD00710)
Type small molecule
Groups approved
Description

Bromodiphenhydramine is an ethanolamine antihistamine with antimicrobial property. Bromodiphenhydramine is used in the control of cutaneous allergies. Ethanolamine antihistamines produce marked sedation in most patients
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Ambodryl Hydrochloride
Amodryl
Bromanautine
Bromazin
Bromazine
Bromazine hydrochloride
Bromdiphenhydramine
Bromdiphenhydramine hydrochloride
Bromdiphenylhydramine Hydrochloride
Bromodiphenhydramine hydrochloride
Salts Not Available
Brand names
Name Company
Bromo-Benadryl
Bromo-Benzdryl
Deserol
Histabromamine
Neo-Benadryl
Brand mixtures
Brand Name Ingredients
Ambenyl Cough Syrup Ammonium Chloride + Bromodiphenhydramine Hydrochloride + Codeine Phosphate + Diphenhydramine Hydrochloride + Potassium Guaiacol Sulphonate
Categories
  • Antihistamines
CAS number 1808-12-4
Weight Average: 334.251
Monoisotopic: 333.072826914
Chemical Formula C17H20BrNO
InChI Key InChIKey=NUNIWXHYABYXKF-UHFFFAOYSA-N
InChI
InChI=1S/C17H20BrNO/c1-19(2)12-13-20-17(14-6-4-3-5-7-14)15-8-10-16(18)11-9-15/h3-11,17H,12-13H2,1-2H3
Plain Text
IUPAC Name
{2-[(4-bromophenyl)(phenyl)methoxy]ethyl}dimethylamine
SMILES
CN(C)CCOC(C1=CC=CC=C1)C1=CC=C(Br)C=C1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Diphenhydramines
Substructures
  • Diphenhydramines
  • Benzyl Alcohols and Derivatives
  • Ethers
  • Benzene and Derivatives
  • Aliphatic and Aryl Amines
  • Aryl Halides
  • Diphenylmethanes
  • Aromatic compounds
  • Halobenzenes
Pharmacology
Indication For management of symptoms related to hay fever and other types of allergy and used to help bring up phlegm, thin secretions, and make a cough productive.
Pharmacodynamics Bromodiphenhydramine is an antihistamine of the ethanolamine class. Ethanolamine antihistamines have significant antimuscarinic activity and produce marked sedation in most patients. In addition to the usual allergic symptoms, the drug also treats irritant cough and nausea, vomiting, and vertigo associated with motion sickness. It also is used commonly to treat drug-induced extrapyramidal symptoms as well as to treat mild cases of Parkinson's disease. Rather than preventing the release of histamine, as do cromolyn and nedocromil, Bromodiphenhydramine competes with free histamine for binding at HA-receptor sites. Bromodiphenhydramine competitively antagonizes the effects of histamine on HA-receptors in the GI tract, uterus, large blood vessels, and bronchial muscle. Ethanolamine derivatives have greater anticholinergic activity than do other antihistamines, which probably accounts for the antidyskinetic action of Bromodiphenhydramine. This anticholinergic action appears to be due to a central antimuscarinic effect, which also may be responsible for its antiemetic effects, although the exact mechanism is unknown.
Mechanism of action Bromodiphenhydramine competes with free histamine for binding at HA-receptor sites. This antagonizes the effects of histamine on HA-receptors, leading to a reduction of the negative symptoms brought on by histamine HA-receptor binding.
Absorption Well absorbed in the digestive tract.
Volume of distribution Not Available
Protein binding 96%
Metabolism
Hepatic (cytochrome P-450 system); some renal.
Route of elimination Not Available
Half life 1 to 4 hours
Clearance Not Available
Toxicity Signs of overdose include wheezing, tightness in the chest, fever, itching, bad cough, blue skin color, fits, swelling of face, lips, tongue, or throat.
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Parke davis div warner lambert co
Packagers Not Available
Dosage forms Not Available
Prices Not Available
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
logP 4 Not Available
Predicted Properties
Property Value Source
water solubility 3.45e-03 g/l ALOGPS
logP 4.16 ALOGPS
logP 4.42 ChemAxon
logS -5 ALOGPS
pKa (strongest basic) 8.87 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 2 ChemAxon
hydrogen donor count 0 ChemAxon
polar surface area 12.47 ChemAxon
rotatable bond count 6 ChemAxon
refractivity 87.55 ChemAxon
polarizability 33.48 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
PubChem Compound 2444 Link_out
PubChem Substance 46506082 Link_out
ChemSpider 2350 Link_out
ChEBI 59177 Link_out
ChEMBL 59177 Link_out
Therapeutic Targets Database DAP001072 Link_out
PharmGKB PA164760854 Link_out
Drug Product Database 469122 Link_out
ATC Codes
  • D04AA32
  • D04AA33
  • R06AA02
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions
Drug Interaction
Tacrine The therapeutic effects of the central acetylcholinesterase inhibitor, Tacrine, and/or the anticholinergic, Bromodiphenhydramine, 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 Bromodiphenhydramine, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Triprolidine Triprolidine and Bromodiphenhydramine, 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 Bromodiphenhydramine, 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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
Transporters

1. Multidrug and toxin extrusion protein 1

Actions: inhibitor

Solute transporter for tetraethylammonium (TEA), 1- methyl-4-phenylpyridinium (MPP), cimetidine, N-methylnicotinamide (NMN), metformin, creatinine, guanidine, procainamide, topotecan, estrone sulfate, acyclovir, ganciclovir and also the zwitterionic cephalosporin, cephalexin and cephradin. Seems to also play a role in the uptake of oxaliplatin (a new platinum anticancer agent). Able to transport paraquat (PQ or N,N-dimethyl-4-4'-bipiridinium); a widely used herbicid. Responsible for the secretion of cationic drugs across the brush border membranes

UniProt ID: Q96FL8 Link_out
Gene: SLC47A1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Ullrich KJ, Rumrich G, David C, Fritzsch G: Bisubstrates: substances that interact with renal contraluminal organic anion and organic cation transport systems. I. Amines, piperidines, piperazines, azepines, pyridines, quinolines, imidazoles, thiazoles, guanidines and hydrazines. Pflugers Arch. 1993 Nov;425(3-4):280-99. Pubmed

2. Solute carrier family 22 member 6

UniProt ID: Q4U2R8 Link_out
Gene: hROAT1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Ullrich KJ, Rumrich G, David C, Fritzsch G: Bisubstrates: substances that interact with renal contraluminal organic anion and organic cation transport systems. I. Amines, piperidines, piperazines, azepines, pyridines, quinolines, imidazoles, thiazoles, guanidines and hydrazines. Pflugers Arch. 1993 Nov;425(3-4):280-99. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:20