Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C16H19BrN2.C4H4O4 |
Molecular Weight | 435.312 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)\C=C/C(O)=O.CN(C)CC[C@@H](C1=CC=C(Br)C=C1)C2=CC=CC=N2
InChI
InChIKey=SRGKFVAASLQVBO-DASCVMRKSA-N
InChI=1S/C16H19BrN2.C4H4O4/c1-19(2)12-10-15(16-5-3-4-11-18-16)13-6-8-14(17)9-7-13;5-3(6)1-2-4(7)8/h3-9,11,15H,10,12H2,1-2H3;1-2H,(H,5,6)(H,7,8)/b;2-1-/t15-;/m0./s1
Molecular Formula | C4H4O4 |
Molecular Weight | 116.0722 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Optical Activity | NONE |
Molecular Formula | C16H19BrN2 |
Molecular Weight | 319.239 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e241d83e-996c-494d-b3fe-97f1ef4809edCurator's Comment: description was created based on several sources, including
https://www.drugs.com/mtm/brompheniramine.html
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.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10212017 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | BROMFED-DM (BROMPHENIRAMINE MALEATE; DEXTROMETHORPHAN HYDROBROMIDE; PSEUDOEPHEDRINE HYDROCHLORIDE) Approved UseFor relief of coughs and upper respiratory symptoms, including nasal congestion, associated with allergy or the common cold. Launch Date1985 |
|||
Palliative | Unknown Approved UseUnknown |
|||
Palliative | Unknown Approved UseUnknown |
Cmax
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 |
T1/2
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 |
PubMed
Title | Date | PubMed |
---|---|---|
Oral facial dyskinesia associated with prolonged use of antihistaminic decongestants. | 1975 Sep 4 |
|
Phenylpropanolamine and mental disturbances. | 1979 Dec 22-29 |
|
Fatal cold medication intoxication in an infant. | 2003 Oct |
|
Electrophysiological effects of brompheniramine on cardiac ion channels and action potential. | 2006 Dec |
|
Characterization of antihistamine-human serum protein interactions by capillary electrophoresis. | 2007 Apr 20 |
|
Evaluation of enantioselective binding of basic drugs to plasma by ACE. | 2007 Aug |
|
Medication administered to children from 0 to 7.5 years in the Avon Longitudinal Study of Parents and Children (ALSPAC). | 2007 Feb |
|
Enantiomeric quality control of antihistamines in pharmaceuticals by affinity electrokinetic chromatography with human serum albumin as chiral selector. | 2007 Jun 5 |
|
Possible role of pseudoephedrine and other over-the-counter cold medications in the deaths of very young children. | 2007 Mar |
|
The effect of achiral calixarenes on chiral separation of propranolol-HCl and brompheniramine maleate in capillary electrophoresis using cyclodextrin as chiral selector. | 2008 Apr |
|
Uniformly sized molecularly imprinted polymers for d-chlorpheniramine: influence of a porogen on their morphology and enantioselectivity. | 2008 Apr 14 |
|
Cough and cold medication use by US children, 1999-2006: results from the slone survey. | 2008 Aug |
|
Indirect fluorescent determination of selected nitro-aromatic and pharmaceutical compounds via UV-photolysis of 2-phenylbenzimidazole-5-sulfonate. | 2008 Feb 15 |
|
H1-antihistamines and oxidative burst of professional phagocytes. | 2009 |
|
Protective effect of pheniramines against mesenteric ischaemia/reperfusion-induced injury. | 2009 Apr |
|
Acute cough: a diagnostic and therapeutic challenge. | 2009 Dec 16 |
|
Arvid Carlsson, and the story of dopamine. | 2010 Jan |
|
Determination of chlorpheniramine in human plasma by HPLC-ESI-MS/MS: application to a dexchlorpheniramine comparative bioavailability study. | 2010 Jul |
|
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | 2011 Jul 14 |
Patents
Sample Use Guides
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9578932
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 14:58:49 GMT 2023
by
admin
on
Fri Dec 15 14:58:49 GMT 2023
|
Record UNII |
BPA9UT29BS
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
CFR |
21 CFR 341.12
Created by
admin on Fri Dec 15 14:58:49 GMT 2023 , Edited by admin on Fri Dec 15 14:58:49 GMT 2023
|
||
|
NCI_THESAURUS |
C29578
Created by
admin on Fri Dec 15 14:58:49 GMT 2023 , Edited by admin on Fri Dec 15 14:58:49 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
2391-03-9
Created by
admin on Fri Dec 15 14:58:49 GMT 2023 , Edited by admin on Fri Dec 15 14:58:49 GMT 2023
|
PRIMARY | |||
|
C015121
Created by
admin on Fri Dec 15 14:58:49 GMT 2023 , Edited by admin on Fri Dec 15 14:58:49 GMT 2023
|
PRIMARY | |||
|
219-236-2
Created by
admin on Fri Dec 15 14:58:49 GMT 2023 , Edited by admin on Fri Dec 15 14:58:49 GMT 2023
|
PRIMARY | |||
|
DBSALT001411
Created by
admin on Fri Dec 15 14:58:49 GMT 2023 , Edited by admin on Fri Dec 15 14:58:49 GMT 2023
|
PRIMARY | |||
|
SUB01626MIG
Created by
admin on Fri Dec 15 14:58:49 GMT 2023 , Edited by admin on Fri Dec 15 14:58:49 GMT 2023
|
PRIMARY | |||
|
m2723
Created by
admin on Fri Dec 15 14:58:49 GMT 2023 , Edited by admin on Fri Dec 15 14:58:49 GMT 2023
|
PRIMARY | Merck Index | ||
|
1178002
Created by
admin on Fri Dec 15 14:58:49 GMT 2023 , Edited by admin on Fri Dec 15 14:58:49 GMT 2023
|
PRIMARY | |||
|
100000087764
Created by
admin on Fri Dec 15 14:58:49 GMT 2023 , Edited by admin on Fri Dec 15 14:58:49 GMT 2023
|
PRIMARY | |||
|
BPA9UT29BS
Created by
admin on Fri Dec 15 14:58:49 GMT 2023 , Edited by admin on Fri Dec 15 14:58:49 GMT 2023
|
PRIMARY | |||
|
CHEMBL1201287
Created by
admin on Fri Dec 15 14:58:49 GMT 2023 , Edited by admin on Fri Dec 15 14:58:49 GMT 2023
|
PRIMARY | |||
|
C61706
Created by
admin on Fri Dec 15 14:58:49 GMT 2023 , Edited by admin on Fri Dec 15 14:58:49 GMT 2023
|
PRIMARY | |||
|
6433334
Created by
admin on Fri Dec 15 14:58:49 GMT 2023 , Edited by admin on Fri Dec 15 14:58:49 GMT 2023
|
PRIMARY | |||
|
BPA9UT29BS
Created by
admin on Fri Dec 15 14:58:49 GMT 2023 , Edited by admin on Fri Dec 15 14:58:49 GMT 2023
|
PRIMARY | |||
|
48936
Created by
admin on Fri Dec 15 14:58:49 GMT 2023 , Edited by admin on Fri Dec 15 14:58:49 GMT 2023
|
PRIMARY | RxNorm | ||
|
DTXSID6047818
Created by
admin on Fri Dec 15 14:58:49 GMT 2023 , Edited by admin on Fri Dec 15 14:58:49 GMT 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
PARENT -> SALT/SOLVATE | |||
|
RACEMATE -> ENANTIOMER | |||
|
PARENT -> SALT/SOLVATE |
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |