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Properties

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Taxonomy

Dexbrompheniramine

Targets (1)

Identification

Name

Dexbrompheniramine

Accession Number

DB00405 (APRD00770)

Type

Small Molecule

Groups

Approved

Description

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

Structure

Similar Structures

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

Product Ingredients

Ingredient	UNII	CAS	InChI Key
Dexbrompheniramine maleate	BPA9UT29BS	2391-03-9	SRGKFVAASLQVBO-DASCVMRKSA-N

Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Unlock Additional Data
Ala-hist Ir	Tablet	2 mg/1	Oral	Poly Pharmaceuticals	2011-08-22	Not applicable
PediaVent	Syrup	2 mg/5mL	Oral	Carwin Associates, Inc	2014-08-04	Not applicable
PediaVent	Tablet, chewable	1 mg/1	Oral	Carwin Associates, Inc	2014-08-05	Not applicable

Additional Data Available

Application Number

A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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Product Code

A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Acticon	Dexbrompheniramine maleate (2 mg/1) + Pseudoephedrine hydrochloride (60 mg/1)	Tablet	Oral	Actipharma, Inc	2015-08-13	Not applicable
Acticon	Dexbrompheniramine maleate (1 mg/5mL) + Pseudoephedrine hydrochloride (30 mg/5mL)	Liquid	Oral	ACTIPHARMA, INC.	2016-07-14	Not applicable
Actidogesic	Dexbrompheniramine maleate (1 mg/1) + Acetaminophen (500 mg/1)	Tablet	Oral	Actipharma, Inc	2016-10-14	Not applicable
Ala-hist PE	Dexbrompheniramine maleate (2 mg/1) + Phenylephrine hydrochloride (10 mg/1)	Tablet	Oral	Poly Pharmaceuticals	2011-09-15	Not applicable
Alahist CF	Dexbrompheniramine maleate (2 g/1) + Dextromethorphan hydrobromide monohydrate (20 g/1) + Phenylephrine hydrochloride (10 g/1)	Tablet	Oral	Poly Pharmaceuticals	2017-09-14	Not applicable
Alahistdm DM	Dexbrompheniramine maleate (2 mg/5mL) + Dextromethorphan hydrobromide monohydrate (15 mg/5mL) + Phenylephrine hydrochloride (7.5 mg/5mL)	Liquid	Oral	Poly Pharmaceuticals, Inc.	2016-09-01	Not applicable
Bio-cnex	Dexbrompheniramine maleate (1 mg/5mL) + Pseudoephedrine hydrochloride (30 mg/5mL)	Liquid	Oral	Advanced Generic Corporation	2017-01-01	Not applicable
Biogesic	Dexbrompheniramine maleate (1 mg/1) + Acetaminophen (500 mg/1)	Tablet	Oral	Advanced Generic Corporation	2017-01-01	Not applicable
Bionatuss DXP	Dexbrompheniramine maleate (2 mg/5mL) + Dextromethorphan hydrobromide monohydrate (20 mg/5mL) + Phenylephrine hydrochloride (10 mg/5mL)	Liquid	Oral	Advanced Generic Corporation	2009-10-01	Not applicable
Chlo Hist	Dexbrompheniramine maleate (1 mg/5mL) + Chlophedianol hydrochloride (12.5 mg/5mL)	Liquid	Oral	R. A. McNeil Company	2014-09-15	Not applicable

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Brompheniramine Maleate Pseudoephedrine HCl	Dexbrompheniramine maleate (1 mg/1mL) + Pseudoephedrine hydrochloride (7.5 mg/1mL)	Liquid	Oral	River's Edge Pharmaceuticals, LLC	2008-06-01	2010-10-31

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.

Target	Actions	Organism
AHistamine H1 receptor	antagonist	Humans

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Additional Data Available

Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available

Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available

Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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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

Pathway	Category
Dexbrompheniramine H1-Antihistamine Action	Drug action

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

Drug	Interaction
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2,5-Dimethoxy-4-ethylamphetamine	2,5-Dimethoxy-4-ethylamphetamine may decrease the sedative and stimulatory activities of Dexbrompheniramine.
2,5-Dimethoxy-4-ethylthioamphetamine	2,5-Dimethoxy-4-ethylthioamphetamine may decrease the sedative and stimulatory activities of Dexbrompheniramine.
4-Bromo-2,5-dimethoxyamphetamine	4-Bromo-2,5-dimethoxyamphetamine may decrease the sedative and stimulatory activities of Dexbrompheniramine.
4-Methoxyamphetamine	The risk or severity of adverse effects can be increased when Dexbrompheniramine is combined with 4-Methoxyamphetamine.
5-methoxy-N,N-dimethyltryptamine	The risk or severity of adverse effects can be increased when Dexbrompheniramine is combined with 5-methoxy-N,N-dimethyltryptamine.
7-Nitroindazole	The risk or severity of adverse effects can be increased when Dexbrompheniramine is combined with 7-Nitroindazole.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline	The risk or severity of adverse effects can be increased when Dexbrompheniramine is combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline.
Abexinostat	The risk or severity of QTc prolongation can be increased when Dexbrompheniramine is combined with Abexinostat.
Acebutolol	The risk or severity of QTc prolongation can be increased when Dexbrompheniramine is combined with Acebutolol.
Acepromazine	The risk or severity of adverse effects can be increased when Dexbrompheniramine is combined with Acepromazine.

Additional Data Available

Extended Description

Extended description of the mechanism of action and particular properties of each drug interaction.

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Severity

A severity rating for each drug interaction, from minor to major.

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Evidence Level

A rating for the strength of the evidence supporting each drug interaction.

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Action

Evidence Level

An effect category for each drug interaction. Know how this interaction affects the subject drug.

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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

R06AB06 — Dexbrompheniramine

R06AB56 — Dexbrompheniramine, combinations

Clinical Trials

Clinical Trials: Not Available

Pharmacoeconomics

Manufacturers

Schering corp sub schering plough corp

Packagers

Poly Pharmaceuticals Inc.

Dosage forms

Form	Route	Strength
Tablet	Oral	2 mg/1
Liquid	Oral
Tablet, extended release	Oral
Tablet; tablet, extended release	Oral
Syrup	Oral
Tablet	Oral
Syrup	Oral	2 mg/5mL
Tablet, chewable	Oral	1 mg/1

Prices

Unit description	Cost	Unit
Ala-hist ir 2 mg tablet	0.82USD	tablet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	113-115	US. Patent 3,030,371.
logP	3.4	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0127 mg/mL	ALOGPS
logP	3.63	ALOGPS
logP	3.75	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Basic)	9.48	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	16.13 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	83.67 m³·mol^-1	ChemAxon
Polarizability	31.84 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	+	0.9648
Blood Brain Barrier	+	0.9576
Caco-2 permeable	+	0.8867
P-glycoprotein substrate	Substrate	0.6242
P-glycoprotein inhibitor I	Non-inhibitor	0.8782
P-glycoprotein inhibitor II	Non-inhibitor	0.93
Renal organic cation transporter	Inhibitor	0.7955
CYP450 2C9 substrate	Non-substrate	0.8345
CYP450 2D6 substrate	Substrate	0.8346
CYP450 3A4 substrate	Substrate	0.5898
CYP450 1A2 substrate	Non-inhibitor	0.9045
CYP450 2C9 inhibitor	Non-inhibitor	0.9071
CYP450 2D6 inhibitor	Inhibitor	0.8932
CYP450 2C19 inhibitor	Non-inhibitor	0.9025
CYP450 3A4 inhibitor	Non-inhibitor	0.8398
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.7748
Ames test	Non AMES toxic	0.9351
Carcinogenicity	Non-carcinogens	0.9349
Biodegradation	Not ready biodegradable	1.0
Rat acute toxicity	3.0758 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9121
hERG inhibition (predictor II)	Inhibitor	0.7207

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	Not Available
MS/MS Spectrum - , positive	LC-MS/MS	splash10-0292-0940000000-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

Details1. Histamine H1 receptor

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

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]
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]
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]
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]
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]
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 May 08, 2019 23:54

Dexbrompheniramine

Identification

Structure for Dexbrompheniramine (DB00405)

Pharmacology

Interactions

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Taxonomy

Targets

References