BROMPHENIRAMINE TANNATE

US Approved OTC

First approved in 1956

Details

Stereochemistry	EPIMERIC
Molecular Formula	C76H52O46.C16H19BrN2
Molecular Weight	2020.438
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN(C)CCC(C1=CC=C(Br)C=C1)C2=NC=CC=C2.OC3=CC(=CC(O)=C3O)C(=O)OC4=CC(=CC(O)=C4O)C(=O)OC[C@H]5O[C@@H](OC(=O)C6=CC(O)=C(O)C(OC(=O)C7=CC(O)=C(O)C(O)=C7)=C6)[C@H](OC(=O)C8=CC(O)=C(O)C(OC(=O)C9=CC(O)=C(O)C(O)=C9)=C8)[C@@H](OC(=O)C%10=CC(O)=C(O)C(OC(=O)C%11=CC(O)=C(O)C(O)=C%11)=C%10)[C@@H]5OC(=O)C%12=CC(O)=C(O)C(OC(=O)C%13=CC(O)=C(O)C(O)=C%13)=C%12

InChI

InChIKey=YZAQFXRNFPSDQX-HBNMXAOGSA-N

InChI=1S/C76H52O46.C16H19BrN2/c77-32-1-22(2-33(78)53(32)92)67(103)113-47-16-27(11-42(87)58(47)97)66(102)112-21-52-63(119-72(108)28-12-43(88)59(98)48(17-28)114-68(104)23-3-34(79)54(93)35(80)4-23)64(120-73(109)29-13-44(89)60(99)49(18-29)115-69(105)24-5-36(81)55(94)37(82)6-24)65(121-74(110)30-14-45(90)61(100)50(19-30)116-70(106)25-7-38(83)56(95)39(84)8-25)76(118-52)122-75(111)31-15-46(91)62(101)51(20-31)117-71(107)26-9-40(85)57(96)41(86)10-26;1-19(2)12-10-15(16-5-3-4-11-18-16)13-6-8-14(17)9-7-13/h1-20,52,63-65,76-101H,21H2;3-9,11,15H,10,12H2,1-2H3/t52-,63-,64+,65-,76+;/m1./s1

HIDE SMILES / InChI

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e241d83e-996c-494d-b3fe-97f1ef4809ed
Curator's Comment: description was created based on several sources, including https://www.drugs.com/mtm/brompheniramine.html

Brompheniramine is an antihistaminergic medication of the propylamine class. It is a first-generation antihistamine, which is used for the treatment of the symptoms of the common cold and allergic rhinitis, such as runny nose, itchy eyes, watery eyes, and sneezing. 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. Brompheniramine is a histamine H1 antagonist 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. Brompheniramine is metabolised by cytochrome P450s. The halogenated alkylamine antihistamines all exhibit optic isomerism and brompheniramine products contain racemic brompheniramine maleate whereas dexbrompheniramine (Drixoral) is the dextrorotary (right-handed) stereoisomer.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Histamine H1 receptor 315 Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10212017	Antagonist 2778

Conditions

Condition	Modality	Highest Phase	Product
Common cold 58 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=06db369d-09fe-4ca2-b98c-705356b7c403	Palliative	Approved 8429	BROMFED-DM (BROMPHENIRAMINE MALEATE; DEXTROMETHORPHAN HYDROBROMIDE; PSEUDOEPHEDRINE HYDROCHLORIDE) Approved Use For relief of coughs and upper respiratory symptoms, including nasal congestion, associated with allergy or the common cold. Launch Date 1985
Nasal congestion and inflammations 4 Sources: https://clinicaltrials.gov/ct2/show/NCT01393561	Palliative	Phase III 656	Unknown Approved Use Unknown
Rhinitis 20 Sources: https://clinicaltrials.gov/ct2/show/NCT01393561	Palliative	Phase III 656	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
11.6 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6128358/	0.13 mg/kg single, oral dose: 0.13 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		BROMPHENIRAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
284 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6128358/	0.13 mg/kg single, oral dose: 0.13 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		BROMPHENIRAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
24.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6128358/	0.13 mg/kg single, oral dose: 0.13 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		BROMPHENIRAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:3183	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3183
MolPort	MolPort-005-935-546	https://www.molport.com/shop/molecule-link/MolPort-005-935-546
eMolecules	901744	https://www.emolecules.com/cgi-bin/more?vid=901744

PubMed

Title	Date	PubMed
Oral facial dyskinesia associated with prolonged use of antihistaminic decongestants.	1975 Sep 4	239337
Phenylpropanolamine and mental disturbances.	1979 Dec 22-29	92706
[Antimycobacterial antihistaminics].	1989 Aug	2513793
Withdrawal symptoms after discontinuation of long-acting brompheniramine maleate.	1994 Dec	7857852
pH-independent large-volume sample stacking of positive or negative analytes in capillary electrophoresis.	2001 Jan	11197179
Toxicity of over-the-counter cough and cold medications.	2001 Sep	11533370
Involvement of calmodulin inhibition in analgesia induced with low doses of intrathecal trifluoperazine.	2002 Feb	11928715
Spermine-induced negative inotropic effect in isolated rat heart, is mediated through the release of ATP.	2003 Jul 1	12818376
First do no harm: managing antihistamine impairment in patients with allergic rhinitis.	2003 May	12743547
Retentivity and enantioselectivity of uniformly sized molecularly imprinted polymers for d-chlorpheniramine and -brompheniramine in hydro-organic mobile phases.	2004 May 5	15093155
Over-the-counter cold medications-postmortem findings in infants and the relationship to cause of death.	2005 Oct	16419411
The combined luminol/isoluminol chemiluminescence method for differentiating between extracellular and intracellular oxidant production by neutrophils.	2006	16805965
Extra- and intracellular formation of reactive oxygen species by human neutrophils in the presence of pheniramine, chlorpheniramine and brompheniramine.	2006 Dec	17159800
Evaluation of enantioselective binding of basic drugs to plasma by ACE.	2007 Aug	17661317
Evaluation of enantioselective binding of antihistamines to human serum albumin by ACE.	2007 Aug	17605150
Medication administered to children from 0 to 7.5 years in the Avon Longitudinal Study of Parents and Children (ALSPAC).	2007 Feb	17200835
The effect of achiral calixarenes on chiral separation of propranolol-HCl and brompheniramine maleate in capillary electrophoresis using cyclodextrin as chiral selector.	2008 Apr	18468383
Potentialities of ITP-CZE method with diode array detection for enantiomeric purity control of dexbrompheniramine in pharmaceuticals.	2008 Apr 14	17618074
Cough and cold medication use by US children, 1999-2006: results from the slone survey.	2008 Aug	18676518
Transient receptor potential vanilloid-1-mediated calcium responses are inhibited by the alkylamine antihistamines dexbrompheniramine and chlorpheniramine.	2008 Dec	19085565
Indirect fluorescent determination of selected nitro-aromatic and pharmaceutical compounds via UV-photolysis of 2-phenylbenzimidazole-5-sulfonate.	2008 Feb 15	18371796
Possibilities of column coupling electrophoresis provided with a fiber-based diode array detection in enantioselective analysis of drugs in pharmaceutical and clinical samples.	2008 Jan 25	17905259
H1-antihistamines and oxidative burst of professional phagocytes.	2009	20027159
Acute cough: a diagnostic and therapeutic challenge.	2009 Dec 16	20015366
Treatment of congestion in upper respiratory diseases.	2010 Apr 8	20463825
Commonly prescribed medications and potential false-positive urine drug screens.	2010 Aug 15	20689123
Arvid Carlsson, and the story of dopamine.	2010 Jan	20174530
Trace determination of pharmaceuticals and other wastewater-derived micropollutants by solid phase extraction and gas chromatography/mass spectrometry.	2010 Jan 22	20015510
Determination of chlorpheniramine in human plasma by HPLC-ESI-MS/MS: application to a dexchlorpheniramine comparative bioavailability study.	2010 Jul	19924675
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.	2011 Jul 14	21599003

Patents

Sample Use Guides

In Vivo Use Guide

Adults and pediatric patients 12 years of age and over: 10 mL (2 teaspoonfuls) every 4 hours. Children 6 to under 12 years of age: 5 mL (1 teaspoonful) every 4 hours. Children 2 to under 6 years of age: 2.5 mL (½ teaspoonful) every 4 hours. Infants 6 months to under 2 years of age:

Route of Administration: Oral

In Vitro Use Guide

The anticholinergic properties of brompheniramine was assessed in an in vitro model of human nasal mucosal glandular secretion. The effective dose reducing methacholine-induced secretion (ED50) was determined. ED50 was 4.10 microM for rompheniramine.

Name

Type

Language

BROMPHENIRAMINE TANNATE

Common Name

English

BROVEX

Brand Name

English

BROMPHENIRAMINE TANNATE [WHO-DD]

Common Name

English

Code System Code Type Description

PUBCHEM

16140045