Dexbrompheniramine

Identification

Summary

Dexbrompheniramine is an antihistamine used to treat allergy symptoms including upper respiratory tract symptoms.

Brand Names
Ala-hist Ir, Ala-hist PE, Dologen, Dologesic Reformulated Jun 2016
Generic Name
Dexbrompheniramine
DrugBank Accession Number
DB00405
Background

Dexbrompheniramine maleate is an antihistamine agent that is used for the treatment of allergic conditions, such as hay fever or urticaria.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 319.239
Monoisotopic: 318.073161265
Chemical Formula
C16H19BrN2
Synonyms
  • (+)-brompheniraminum
  • (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
  • Dexbrompheniramine
  • Dexbrompheniraminum

Pharmacology

Indication

For treatment and relief of symptoms of allergies, hay fever, and colds

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Symptomatic treatment ofAllergic rhinitis••• •••
Symptomatic treatment ofUpper respiratory allergies••• •••
Contraindications & Blackbox Warnings
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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
Humans
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

Adverse Effects
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Toxicity

Signs of an overdose include fast or irregular heartbeat, mental or mood changes, tightness in the chest, and unusual tiredness or weakness.

Pathways
PathwayCategory
Dexbrompheniramine H1-Antihistamine ActionDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Dexbrompheniramine is combined with 1,2-Benzodiazepine.
AcetazolamideThe risk or severity of CNS depression can be increased when Dexbrompheniramine is combined with Acetazolamide.
AcetophenazineThe risk or severity of CNS depression can be increased when Dexbrompheniramine is combined with Acetophenazine.
AcrivastineThe risk or severity of QTc prolongation can be increased when Dexbrompheniramine is combined with Acrivastine.
AdenosineThe risk or severity of QTc prolongation can be increased when Dexbrompheniramine is combined with Adenosine.
Food Interactions
  • Avoid alcohol. Taking with alcohol may increase drowsiness.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Dexbrompheniramine maleateBPA9UT29BS2391-03-9SRGKFVAASLQVBO-DASCVMRKSA-N
International/Other Brands
Disophrol (Schering) / Drixoral (Schering )
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Ala-hist IrTablet2 mg/1OralPoly Pharmaceuticals, Inc.2011-08-22Not applicableUS flag
PediaVentTablet, chewable1 mg/1OralCarwin Associates, Inc2014-08-05Not applicableUS flag
PediaVentSyrup2 mg/5mLOralCarwin Associates, Inc2014-08-04Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Accu Tuss DMDexbrompheniramine maleate (2 mg/5mL) + Dextromethorphan hydrobromide monohydrate (15 mg/5mL) + Phenylephrine hydrochloride (7.5 mg/5mL)LiquidOralAccoria, Inc2023-10-20Not applicableUS flag
ActiconDexbrompheniramine maleate (1 mg/5mL) + Pseudoephedrine hydrochloride (30 mg/5mL)LiquidOralACTIPHARMA, INC.2016-07-14Not applicableUS flag
ActiconDexbrompheniramine maleate (2 mg/1) + Pseudoephedrine hydrochloride (60 mg/1)TabletOralActipharma, Inc2015-08-13Not applicableUS flag
ActiconDexbrompheniramine maleate (2 mg/5mL) + Pseudoephedrine hydrochloride (60 mg/5mL)SolutionOralActipharma, Inc2022-02-15Not applicableUS flag
ActidogesicDexbrompheniramine maleate (1 mg/1) + Acetaminophen (500 mg/1)TabletOralActipharma, Inc2016-10-14Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Ala-hist IrDexbrompheniramine maleate (2 mg/1)TabletOralPoly Pharmaceuticals, Inc.2011-08-22Not applicableUS flag
Alahist PEDexbrompheniramine maleate (2 mg/1) + Phenylephrine hydrochloride (7.5 mg/1)TabletOralPoly Pharmaceuticals, Inc.2020-08-24Not applicableUS flag
Brompheniramine Maleate Pseudoephedrine HClDexbrompheniramine maleate (1 mg/1mL) + Pseudoephedrine hydrochloride (7.5 mg/1mL)LiquidOralRiver's Edge Pharmaceuticals, LLC2008-06-012010-10-31US flag

Categories

ATC Codes
R06AB06 — DexbrompheniramineR06AB56 — Dexbrompheniramine, combinations
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Amine / Aralkylamine / Aromatic heteromonocyclic compound / Aryl bromide / Aryl halide / Azacycle / Benzenoid / Bromobenzene / Halobenzene / Heteroaromatic compound
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
brompheniramine (CHEBI:59269)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
75T64B71RP
CAS number
132-21-8
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

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
Human Metabolome Database
HMDB0014549
PubChem Compound
16960
PubChem Substance
46505186
ChemSpider
16068
RxNav
22696
ChEBI
59269
ChEMBL
CHEMBL1201287
ZINC
ZINC000000000096
Therapeutic Targets Database
DAP001068
PharmGKB
PA164746251
Wikipedia
Dexbrompheniramine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
  • Schering corp sub schering plough corp
Packagers
  • Poly Pharmaceuticals Inc.
Dosage Forms
FormRouteStrength
SolutionOral
TabletOral2 mg/1
LiquidOral
Tablet, extended releaseOral
TabletOral
Tablet; tablet, extended releaseOral
SyrupOral2 mg/5mL
Tablet, chewableOral1 mg/1
SyrupOral
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-MSsplash10-0a4i-9050000000-d51445063b50de15bdcc
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-0292-0940000000-f369442eba5344b3ecb4
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0292-0940000000-f369442eba5344b3ecb4
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0009000000-8df93fa5ad3493aa4111
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0009000000-615031c9863c28108e0f
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00xr-9058000000-79d59f3d1387fa225ee7
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-016s-9454000000-72507f314a6e9dc5fbf3
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00lr-2910000000-cf47f8cc138e09cf7622
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9120000000-2bc9148808a8e32bfa7a
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-170.9342217
predicted
DarkChem Lite v0.1.0
[M-H]-164.86452
predicted
DeepCCS 1.0 (2019)
[M+H]+173.2816217
predicted
DarkChem Lite v0.1.0
[M+H]+167.22252
predicted
DeepCCS 1.0 (2019)
[M+Na]+171.3594217
predicted
DarkChem Lite v0.1.0
[M+Na]+173.31566
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 03, 2024 02:25