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
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
Molecular Formula | C76H52O46 |
Molecular Weight | 1701.1985 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 3 |
Optical Activity | UNSPECIFIED |
Molecular Formula | C16H19BrN2 |
Molecular Weight | 319.239 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
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 |
|
[Antimycobacterial antihistaminics]. | 1989 Aug |
|
Withdrawal symptoms after discontinuation of long-acting brompheniramine maleate. | 1994 Dec |
|
Toxicity of over-the-counter cough and cold medications. | 2001 Sep |
|
Update on medical treatment of ejaculatory disorders. | 2002 Dec |
|
Involvement of calmodulin inhibition in analgesia induced with low doses of intrathecal trifluoperazine. | 2002 Feb |
|
Spermine-induced negative inotropic effect in isolated rat heart, is mediated through the release of ATP. | 2003 Jul 1 |
|
First do no harm: managing antihistamine impairment in patients with allergic rhinitis. | 2003 May |
|
Antihistamines in the treatment of dermatitis. | 2003 Nov-Dec |
|
Fatal cold medication intoxication in an infant. | 2003 Oct |
|
Retentivity and enantioselectivity of uniformly sized molecularly imprinted polymers for d-chlorpheniramine and -brompheniramine in hydro-organic mobile phases. | 2004 May 5 |
|
Laboratory exposures to staphylococcal enterotoxin B. | 2004 Sep |
|
Nimesulide-induced fixed drug eruption. | 2005 Sep-Oct |
|
Antiradical effects of antihistamines in human blood. Structure-activity relationship. | 2006 Apr |
|
Extra- and intracellular formation of reactive oxygen species by human neutrophils in the presence of pheniramine, chlorpheniramine and brompheniramine. | 2006 Dec |
|
Analysis of pharmaceutical preparations containing antihistamine drugs by micellar liquid chromatography. | 2006 Feb 13 |
|
Optimization by factorial design of a capillary zone electrophoresis method for the simultaneous separation of antihistamines. | 2006 May 1 |
|
Evaluation of enantioselective binding of basic drugs to plasma by ACE. | 2007 Aug |
|
Evaluation of enantioselective binding of antihistamines to human serum albumin 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 |
|
First-generation H1 antihistamines found in pilot fatalities of civil aviation accidents, 1990-2005. | 2007 May |
|
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 |
|
Potentialities of ITP-CZE method with diode array detection for enantiomeric purity control of dexbrompheniramine in pharmaceuticals. | 2008 Apr 14 |
|
Drug-liposome distribution phenomena studied by capillary electrophoresis-frontal analysis. | 2008 Aug |
|
Indirect fluorescent determination of selected nitro-aromatic and pharmaceutical compounds via UV-photolysis of 2-phenylbenzimidazole-5-sulfonate. | 2008 Feb 15 |
|
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 |
|
Blockade of HERG K+ channel by an antihistamine drug brompheniramine requires the channel binding within the S6 residue Y652 and F656. | 2008 Mar |
|
H1-antihistamines and oxidative burst of professional phagocytes. | 2009 |
|
Pheniramines and oxidative burst of blood phagocytes during ischaemia/reperfusion. | 2009 Apr |
|
Protective effect of pheniramines against mesenteric ischaemia/reperfusion-induced injury. | 2009 Apr |
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Acute cough: a diagnostic and therapeutic challenge. | 2009 Dec 16 |
|
Comparison of chiral separation of basic drugs in capillary electrophoresis and liquid chromatography using neutral and negatively charged cyclodextrins. | 2009 Jul 10 |
|
A novel flow cytometric high throughput assay for a systematic study on molecular mechanisms underlying T cell receptor-mediated integrin activation. | 2009 Jun 25 |
|
Halogenation effects of pheniramines on the complexation with beta-cyclodextrin. | 2009 Oct 15 |
|
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
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Edited
Fri Dec 15 21:31:26 GMT 2023
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Record UNII |
NQD5087V38
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Record Status |
Validated (UNII)
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Record Version |
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