You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameDexbrompheniramine
Accession NumberDB00405  (APRD00770)
TypeSmall Molecule
GroupsApproved
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
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ala-hist Irtablet2 mg/1oralPoly Pharmaceuticals, Inc.2011-08-22Not applicableUs
Pediaventsyrup2 mg/5mLoralCar Win Pharmaceutical Associates, Llc2014-08-04Not applicableUs
Pediaventtablet, chewable1 mg/1oralCar Win Pharmaceutical Associates, Llc2014-08-05Not applicableUs
Unapproved/Other Products Not Available
International Brands
NameCompany
DisophrolSchering
DrixoralSchering
Brand mixtures
NameLabellerIngredients
ActiconActipharma, Inc
Ala-hist PEPoly Pharmaceuticals, Inc.
Bionatuss DxpAdvanced Generic Corporation
Chlo HistR. A. Mc Neil Company
Chlo TussR.A. Mc Neil Company
ConexLlorens Pharmaceuticals International Division
Coricidin 'd' Nasal and Sinus CongestionSchering Plough Healthcare Products Canada, A Division Of Schering Canada Inc.
Coricidin D Nasal and Sinus Congestion TabletsSchering Plough Healthcare Products Canada, A Division Of Schering Canada Inc.
DallergyLaser Pharmaceuticals, LLC
Dexbrompherniramine Maleate and Pseudoephedrine Sulfate 6mg/120mgKvk Tech, Inc.
DologenKramer Novis
Dologen 325Kramer Novis
Drixoral Cold & SinusBayer Inc Consumer Care
Drixoral Day/night - Srt/tabsSchering Plough Canada Inc
Drixoral SyrupSchering Plough Canada Inc
Drixtab TabSchering Plough Canada Inc
G-con-XMc Laren Medical
G-dologenKramer Novis
G-P-tuss DxpKramer Novis
M-end DmxR. A. Mc Neil Company
M-end Max DR.A. Mc Neil Company
Panatuss DxpSeyer Pharmatec, Inc.
Panatuss Pediatric Drops DxpSeyer Pharmatec, Inc.
Supress AKramer Novis
Salts
Name/CASStructureProperties
Dexbrompheniramine maleate
ThumbNot applicableDBSALT001411
Categories
UNII75T64B71RP
CAS number132-21-8
WeightAverage: 319.239
Monoisotopic: 318.073161265
Chemical FormulaC16H19BrN2
InChI KeyInChIKey=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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPheniramines
Direct ParentPheniramines
Alternative Parents
Substituents
  • Pheniramine
  • Phenylpropylamine
  • Aralkylamine
  • Halobenzene
  • Bromobenzene
  • Benzenoid
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl bromide
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organobromide
  • Organohalogen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationFor treatment and relief of symptoms of allergies, hay fever, and colds
PharmacodynamicsIn 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 actionDexbrompheniramine 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.
Related Articles
AbsorptionAntihistamines are well absorbed from the gastrointestinal tract after oral administration.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

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

Route of eliminationNot Available
Half life25 hours
ClearanceNot Available
ToxicitySigns 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
Manufacturers
  • Schering corp sub schering plough corp
Packagers
Dosage forms
FormRouteStrength
Tabletoral2 mg/1
Syruporal
Tabletoral
Tablet, extended releaseoral
Tablet (extended-release)oral
Tablet (extended-release); tabletoral
Liquidoral
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.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point113-115US. 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 RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot 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 ReferencesNot Available
External Links
ATC CodesR06AB06R06AB56
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AmphetamineAmphetamine may decrease the sedative activities of Dexbrompheniramine.
AzelastineDexbrompheniramine may increase the central nervous system depressant (CNS depressant) activities of Azelastine.
BaclofenThe risk or severity of adverse effects can be increased when Baclofen is combined with Dexbrompheniramine.
BrimonidineBrimonidine may increase the central nervous system depressant (CNS depressant) activities of Dexbrompheniramine.
CathinoneCathinone may decrease the sedative activities of Dexbrompheniramine.
Cimetropium BromideDexbrompheniramine may increase the anticholinergic activities of Cimetropium Bromide.
EluxadolineDexbrompheniramine may increase the activities of Eluxadoline.
EthanolDexbrompheniramine may increase the central nervous system depressant (CNS depressant) activities of Ethanol.
Ipratropium bromideIpratropium bromide may increase the anticholinergic activities of Dexbrompheniramine.
LorazepamThe risk or severity of adverse effects can be increased when Lorazepam is combined with Dexbrompheniramine.
MorphineThe risk or severity of adverse effects can be increased when Dexbrompheniramine is combined with Morphine.
ParoxetineThe risk or severity of adverse effects can be increased when Dexbrompheniramine is combined with Paroxetine.
ProcyclidineThe risk or severity of adverse effects can be increased when Procyclidine is combined with Dexbrompheniramine.
RamosetronDexbrompheniramine may increase the activities of Ramosetron.
TacrineThe therapeutic efficacy of Dexbrompheniramine can be decreased when used in combination with Tacrine.
TrichlormethiazideThe serum concentration of Trichlormethiazide can be increased when it is combined with Dexbrompheniramine.
Food InteractionsNot Available

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 catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system.
Gene Name:
HRH1
Uniprot ID:
P35367
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 ]
Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on November 30, 2015 12:10