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
Synonyms
  • (+)-Brompheniraminum
  • (+)-parabromdylamine
  • (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
  • Dexbrompheniraminum
  • Parabromodylamine
Product Ingredients
IngredientUNIICASInChI Key
Dexbrompheniramine maleateBPA9UT29BS2391-03-9SRGKFVAASLQVBO-DASCVMRKSA-N
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ala-hist IrTablet2 mg/1OralPoly Pharmaceuticals2011-08-22Not applicableUs
PediaVentTablet, chewable1 mg/1OralCarwin Associates, Inc2014-08-05Not applicableUs
PediaVentSyrup2 mg/5mLOralCarwin Associates, Inc2014-08-04Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
ActiconDexbrompheniramine maleate (2 mg/1) + Pseudoephedrine hydrochloride (60 mg/1)TabletOralActipharma, Inc2015-08-13Not applicableUs
ActiconDexbrompheniramine maleate (1 mg/5mL) + Pseudoephedrine hydrochloride (30 mg/5mL)LiquidOralActipharma, Inc2016-07-14Not applicableUs
ActidogesicDexbrompheniramine maleate (1 mg/1) + Acetaminophen (500 mg/1)TabletOralActipharma, Inc2016-10-14Not applicableUs
Ala-hist PEDexbrompheniramine maleate (2 mg/1) + Phenylephrine hydrochloride (10 mg/1)TabletOralPoly Pharmaceuticals2011-09-15Not applicableUs
Alahist CFDexbrompheniramine maleate (2 g/1) + Dextromethorphan hydrobromide monohydrate (20 g/1) + Phenylephrine hydrochloride (10 g/1)TabletOralPoly Pharmaceuticals2017-09-14Not applicableUs
Alahistdm DMDexbrompheniramine maleate (2 mg/5mL) + Dextromethorphan hydrobromide monohydrate (15 mg/5mL) + Phenylephrine hydrochloride (7.5 mg/5mL)LiquidOralPoly Pharmaceuticals2016-09-01Not applicableUs
Bio-cnexDexbrompheniramine maleate (1 mg/5mL) + Pseudoephedrine hydrochloride (30 mg/5mL)LiquidOralAdvanced Generic Corporation2017-01-01Not applicableUs
BiogesicDexbrompheniramine maleate (1 mg/1) + Acetaminophen (500 mg/1)TabletOralAdvanced Generic Corporation2017-01-01Not applicableUs
Bionatuss DXPDexbrompheniramine maleate (2 mg/5mL) + Dextromethorphan hydrobromide monohydrate (20 mg/5mL) + Phenylephrine hydrochloride (10 mg/5mL)LiquidOralAdvanced Generic Corporation2009-10-01Not applicableUs
Chlo HistDexbrompheniramine maleate (1 mg/5mL) + Chlophedianol hydrochloride (12.5 mg/5mL)LiquidOralR. A. McNeil Company2014-09-15Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Brompheniramine Maleate Pseudoephedrine HClDexbrompheniramine maleate (1 mg/1mL) + Pseudoephedrine hydrochloride (7.5 mg/1mL)LiquidOralRiver's Edge Pharmaceuticals, LLC2008-06-012010-10-31Us
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.

TargetActionsOrganism
AHistamine H1 receptor
antagonist
Human
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
PathwayCategory
Dexbrompheniramine H1-Antihistamine ActionDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
2,5-Dimethoxy-4-ethylamphetamine2,5-Dimethoxy-4-ethylamphetamine may decrease the sedative and stimulatory activities of Dexbrompheniramine.
2,5-Dimethoxy-4-ethylthioamphetamine2,5-Dimethoxy-4-ethylthioamphetamine may decrease the sedative and stimulatory activities of Dexbrompheniramine.
3,4-Methylenedioxyamphetamine3,4-Methylenedioxyamphetamine may decrease the sedative and stimulatory activities of Dexbrompheniramine.
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may decrease the sedative and stimulatory activities of Dexbrompheniramine.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when Dexbrompheniramine is combined with 4-Methoxyamphetamine.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of adverse effects can be increased when Dexbrompheniramine is combined with 5-methoxy-N,N-dimethyltryptamine.
7-NitroindazoleThe risk or severity of adverse effects can be increased when Dexbrompheniramine is combined with 7-Nitroindazole.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of adverse effects can be increased when Dexbrompheniramine is combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline.
AbexinostatThe risk or severity of QTc prolongation can be increased when Dexbrompheniramine is combined with Abexinostat.
AcepromazineThe risk or severity of adverse effects can be increased when Dexbrompheniramine is combined with Acepromazine.
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
R06AB56 — Dexbrompheniramine, combinationsR06AB06 — Dexbrompheniramine

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
  • Schering corp sub schering plough corp
Packagers
  • Poly Pharmaceuticals Inc.
Dosage forms
FormRouteStrength
TabletOral2 mg/1
LiquidOral
Tablet, extended releaseOral
Tablet; tablet, extended releaseOral
SyrupOral
TabletOral
SyrupOral2 mg/5mL
Tablet, chewableOral1 mg/1
Prices
Unit descriptionCostUnit
Ala-hist ir 2 mg tablet0.82USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)113-115US. Patent 3,030,371.
logP3.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0127 mg/mLALOGPS
logP3.63ALOGPS
logP3.75ChemAxon
logS-4.4ALOGPS
pKa (Strongest Basic)9.48ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area16.13 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity83.67 m3·mol-1ChemAxon
Polarizability31.84 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9648
Blood Brain Barrier+0.9576
Caco-2 permeable+0.8867
P-glycoprotein substrateSubstrate0.6242
P-glycoprotein inhibitor INon-inhibitor0.8782
P-glycoprotein inhibitor IINon-inhibitor0.93
Renal organic cation transporterInhibitor0.7955
CYP450 2C9 substrateNon-substrate0.8345
CYP450 2D6 substrateSubstrate0.8346
CYP450 3A4 substrateSubstrate0.5898
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8398
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7748
Ames testNon AMES toxic0.9351
CarcinogenicityNon-carcinogens0.9349
BiodegradationNot ready biodegradable1.0
Rat acute toxicity3.0758 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9121
hERG inhibition (predictor II)Inhibitor0.7207
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0292-0940000000-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
Human
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
  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:9691225]
  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:1680053]
  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:1970615]
  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:7714410]
  5. 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]
  6. 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 October 01, 2018 16:38