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Identification
NameBromodiphenhydramine
Accession NumberDB01237  (APRD00710)
TypeSmall Molecule
GroupsApproved
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
Synonyms
SynonymLanguageCode
2-(P-Bromo-alpha-phenylbenzyloxy)-N,N-dimethylethylamineNot AvailableNot Available
beta-(P-Bromobenzhydryloxy)ethyldimethylamineNot AvailableNot Available
beta-Dimethylaminoethyl P-bromobenzhydryl etherNot AvailableNot Available
BromazinaNot AvailableNot Available
BromazineNot AvailableINN
BromazinumNot AvailableNot Available
BromodiphenhydramineNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixtures
Brand NameIngredients
Ambenyl Cough SyrupAmmonium Chloride + Bromodiphenhydramine Hydrochloride + Codeine Phosphate + Diphenhydramine Hydrochloride + Potassium Guaiacol Sulphonate
Salts
Name/CASStructureProperties
Bromazine hydrochloride
1808-12-4
Thumb
  • InChI Key: ZQDJSWUEGOYDGT-UHFFFAOYNA-N
  • Monoisotopic Mass: 369.049504653
  • Average Mass: 370.712
DBSALT000791
Categories
CAS number118-23-0
WeightAverage: 334.251
Monoisotopic: 333.072826914
Chemical FormulaC17H20BrNO
InChI KeyNUNIWXHYABYXKF-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
IUPAC Name
{2-[(4-bromophenyl)(phenyl)methoxy]ethyl}dimethylamine
SMILES
CN(C)CCOC(C1=CC=CC=C1)C1=CC=C(Br)C=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentDiphenylmethanes
Alternative Parents
Substituents
  • Diphenylmethane
  • Benzylether
  • Halobenzene
  • Bromobenzene
  • Aryl halide
  • Aryl bromide
  • Tertiary aliphatic amine
  • Tertiary amine
  • Ether
  • Dialkyl ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organobromide
  • Organohalogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor 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.
PharmacodynamicsBromodiphenhydramine 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 actionBromodiphenhydramine 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.
AbsorptionWell absorbed in the digestive tract.
Volume of distributionNot Available
Protein binding96%
Metabolism

Hepatic (cytochrome P-450 system); some renal.

Route of eliminationNot Available
Half life1 to 4 hours
ClearanceNot Available
ToxicitySigns 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9871
Blood Brain Barrier+0.9525
Caco-2 permeable+0.7916
P-glycoprotein substrateSubstrate0.6199
P-glycoprotein inhibitor INon-inhibitor0.6681
P-glycoprotein inhibitor IINon-inhibitor0.7076
Renal organic cation transporterInhibitor0.7733
CYP450 2C9 substrateNon-substrate0.8289
CYP450 2D6 substrateSubstrate0.7231
CYP450 3A4 substrateSubstrate0.6411
CYP450 1A2 substrateInhibitor0.7747
CYP450 2C9 substrateNon-inhibitor0.8483
CYP450 2D6 substrateInhibitor0.8438
CYP450 2C19 substrateNon-inhibitor0.719
CYP450 3A4 substrateNon-inhibitor0.917
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5526
Ames testNon AMES toxic0.8547
CarcinogenicityNon-carcinogens0.6627
BiodegradationNot ready biodegradable0.9892
Rat acute toxicity2.7517 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.5627
hERG inhibition (predictor II)Inhibitor0.7917
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00345 mg/mLALOGPS
logP4.16ALOGPS
logP4.42ChemAxon
logS-5ALOGPS
pKa (Strongest Basic)8.87ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.47 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity87.55 m3·mol-1ChemAxon
Polarizability33.48 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

DrugSyn.org

US2527963
General ReferenceNot Available
External Links
ATC CodesR06AA01
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
TacrineThe 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.
TrimethobenzamideTrimethobenzamide and Bromodiphenhydramine, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
TriprolidineTriprolidine 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.
TrospiumTrospium and Bromodiphenhydramine, two anticholinergics, may cause additive anticholinergic effects and enhanced adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Food InteractionsNot Available

Targets

1. Histamine H1 receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Histamine H1 receptor P35367 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Multidrug and toxin extrusion protein 1 Q96FL8 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Solute carrier family 22 member 6 Q4U2R8 Details

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

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Drug created on June 13, 2005 07:24 / Updated on October 08, 2013 14:22