brompheniramine maleate
Trade name: dimetane
Approved
Aug 23, 1957
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. — NCATS
Clinical trial activity
4 trials · 4 clinical orgs · 39 marketing orgs
Earliest trial started Mar 1, 2009 (NCT00894634)
Timeline
1950s
- Aug 23, 1957
Wyeth — Earliest FDA Approval
- Aug 23, 1957
Wyeth — NDA Organization
- Aug 23, 1957
Wyeth — NDA Secondary Org
- Sep 29, 1958
American Home Products — NDA Secondary Org
1970s
- May 17, 1974
Lannett Company, Inc. — Marketing Organization
- Apr 7, 1975
Barr Laboratories — Marketing Organization
- Dec 17, 1975
Teva — Marketing Organization
- Dec 19, 1975
Upsher-Smith Laboratories — Marketing Organization
- May 20, 1976
Watson Pharmaceuticals — Marketing Organization
- Aug 19, 1977
Lumara Health — Marketing Organization
- Apr 26, 1978
Mylan — Marketing Organization
- Aug 24, 1978
Nexgen Pharma, Inc — Marketing Organization
- Oct 26, 1979
Newtron Pharmaceuticals — Marketing Organization
1980s
- Jul 16, 1981
Alpharma — Marketing Organization
- Aug 24, 1984
AH Robins — Marketing Organization
- Aug 24, 1984
AH Robins — NDA Secondary Org
- Jun 7, 1985
Xttrium Laboratories — Marketing Organization
- Jun 7, 1985
PHARMOBEDIENT — Marketing Organization
- Dec 22, 1988
Wockhardt — Marketing Organization
2000s
- Jan 1, 2009
Earliest Phase 3 Sponsor(trial)
2010s
- Jul 15, 2014
Paddock Laboratories — Marketing Organization
- Jul 15, 2014
Padagis Us — Marketing Organization
- Jul 21, 2014
Vintage — Marketing Organization
- Jul 21, 2014
Pharmaceutical Associates — Marketing Organization
- Sep 20, 2016
Acella Pharmaceuticals — Marketing Organization
- Feb 27, 2017
Taro Pharmaceuticals — Marketing Organization
- Feb 27, 2017
Sun Pharmaceuticals — Marketing Organization
- Dec 4, 2018
Mayne Pharma — Marketing Organization
- Dec 4, 2018
Dr. Reddy's Laboratories — Marketing Organization
2020s
- Apr 17, 2020
Chartwell Pharmaceuticals — Marketing Organization
- Jun 16, 2020
Wes Pharma Inc — Marketing Organization
- Jun 16, 2020
Eywa Pharma — Marketing Organization
- Jun 16, 2020
HIBROW HLTHCARE — Marketing Organization
- Jul 14, 2020
Alkem Labs Ltd — Marketing Organization
- Sep 30, 2020
Esteve Labs — Marketing Organization
- Sep 30, 2020
Bionpharma Inc — Marketing Organization
- Nov 5, 2020
Rhodes Pharmaceuticals, L.P. — Marketing Organization
Indications
Approved for
Mechanism of action
- Histamine H1 receptorANTAGONIST
HRH1 antagonist
Combination products
dimetane-dx
with dextromethorphan, pseudoephedrine
Also known as bromfed-dm
efidac 24 pseudoephedrine hydrochloride/brompheniramine maleate
with pseudoephedrine
Approval history
- approvedAug 23, 1957
Chemistry & pharmacology
SMILES
CN(C)CCC(c1ccc(Br)cc1)c1ccccn1- Mol. weight
- 319.25 g/mol
- Lipinski Ro5
- Pass
- Rule of 3
- No
- Chirality
- Racemic Mixture
- Inorganic
- No
- Polymer
- No
- Delivery
- Oral, Parenteral
- Availability
- Prescription Only
Oral
Yes
Parenteral
Yes
Topical
No
Sources
- ChEMBLCHEMBL811 ↗
- WikipediaBrompheniramine ↗
- NCATSH57G17P2FN ↗
- ChEMBLCHEMBL1200961 ↗
- ChEMBLCHEMBL1200638 ↗
Also known as
- 1-(p-bromophenyl)-1-(2-pyridyl)-3-dimethylaminopropane
- 1-(p-bromophenyl)-1-(2-pyridyl)-3-dimethylaminopropane
- 2-(p-bromo-alpha-(2-dimethylaminoethyl)benzyl)pyridine
- 2-(p-bromo-alpha-(2-dimethylaminoethyl)benzyl)pyridine
- [3-(4-bromo-phenyl)-3-pyridin-2-yl-propyl]-dimethyl-amine
- [3-(4-bromo-phenyl)-3-pyridin-2-yl-propyl]-dimethyl-amine
- 3-(4-bromophenyl)-n,n-dimethyl-3-(2-pyridinyl)-1-propanamine
- 3-(4-bromophenyl)-n,n-dimethyl-3-(2-pyridinyl)-1-propanamine
- 3-(p-bromophenyl)-3-(2-pyridyl)-n,n-dimethylpropylamine
- 3-(p-bromophenyl)-3-(2-pyridyl)-n,n-dimethylpropylamine
- bpn
- bpn
- bromfed
- bromfed
- bromfenex
- bromfenex
- bromfeniramina
- bromfeniramina
- bromopheniramine
- bromphen
- brompheniramin
- brompheniramin
- brompheniramine
- brompheniramine
- brompheniramine
- brompheniramine
- brompheniramine
- brompheniramine
- brompheniramine
- brompheniramine
- brompheniramine
- brompheniramine
- bromphéniramine
- bromphéniramine
- brompheniramine fumarate
- brompheniramine fumarate
- brompheniramine maleate
- brompheniramine maleate
- brompheniramine maleate
- brompheniramine maleate
- brompheniramine maleate
- brompheniramine maleate, pseudoephedrine hydrochloride drug combination
- brompheniramine, pseudoephedrine drug combination
- brompheniraminum
- brompheniraminum
- bronpheniramine
- dimegan
- dimegan
- dimetane
- dimetane
- dimetane
- dimetane-ten
- dimetane-ten
- dimetapp
- dimetapp
- dimetapp
- dimotane
- dimotane
- dimotane l.a.
- disomer
- drixoril
- lodrane
- parabromdylamine
- parabromdylamine maleate
- parabromdylamine maleate
- parabromodylamine
- parabromodylamine
- parabromodylamine
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT01393548 | Phase 3 | Aug 1, 2014 | Ache Laboratorios Farmaceuticos S.A. |
| NCT01177852 | Phase 3 | Oct 1, 2011 | Ache Laboratorios Farmaceuticos S.A. |
| NCT00967759 | Phase 3 | Aug 26, 2009 | Ache Laboratorios Farmaceuticos S.A., University of Sao Paulo |
| NCT00894634 | N/A | Mar 1, 2009 | Pfizer, Wyeth |
Organizations
Research & Development (4)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| Ache Laboratorios Farmaceuticos S.A. | For profit | 3 | 3 | 1 | 2009 |
| Pfizer | For profit | 1 | 1 | 1 | 2009 |
| University of Sao Paulo | Academic/Hospital | 1 | 0 | 1 | 2009 |
| Wyeth | For profit | 1 | 0 | 1 | 2009 |
Marketing (48)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| AH Robins | For profit | MKTG | Aug 24, 1984 |
| AH Robins | For profit | NDA2 | Aug 24, 1984 |
| Acella Pharmaceuticals | For profit | MKTG | Sep 20, 2016 |
| Acella Pharmaceuticals | For profit | SYN | Sep 20, 2016 |
| Alkem Labs Ltd | For profit | MKTG | Jul 14, 2020 |
| Alpharma | For profit | MKTG | Jul 16, 1981 |
| Alza | For profit | MKTG | Mar 29, 1996 |
| Alza | For profit | NDA2 | Mar 29, 1996 |
| American Home Products | For profit | NDA2 | Sep 29, 1958 |
| Barr Laboratories | For profit | MKTG | Apr 7, 1975 |
| Bionpharma Inc | For profit | MKTG | Sep 30, 2020 |
| Chartwell Pharmaceuticals | For profit | MKTG | Apr 17, 2020 |
| Dow Chemical | For profit | MKTG | — |
| Dr. Reddy's Laboratories | For profit | MKTG | Dec 4, 2018 |
| Esteve Labs | For profit | MKTG | Sep 30, 2020 |
| Eywa Pharma | For profit | MKTG | Jun 16, 2020 |
| HIBROW HLTHCARE | For profit | MKTG | Jun 16, 2020 |
| Lannett Company, Inc. | For profit | SYN | Apr 17, 2020 |
| Lannett Company, Inc. | For profit | MKTG | May 17, 1974 |
| Lumara Health | For profit | MKTG | Aug 19, 1977 |
| Mayne Pharma | For profit | MKTG | Dec 4, 2018 |
| Mylan | For profit | MKTG | Apr 26, 1978 |
| NYLOS | For profit | MKTG | — |
| Newtron Pharmaceuticals | For profit | MKTG | Oct 26, 1979 |
| Nexgen Pharma, Inc | For profit | MKTG | Aug 24, 1978 |
| PHARMOBEDIENT | For profit | MKTG | Jun 7, 1985 |
| Padagis Us | For profit | MKTG | Jul 15, 2014 |
| Paddock Laboratories | For profit | SYN | Jul 15, 2014 |
| Paddock Laboratories | For profit | MKTG | Jul 15, 2014 |
| Par Pharmaceuticals | For profit | MKTG | — |
| Pharmaceutical Associates | For profit | MKTG | Jul 21, 2014 |
| Phoenix Laboratories | For profit | MKTG | — |
| Rhodes Pharmaceuticals, L.P. | For profit | MKTG | Nov 5, 2020 |
| Sun Pharmaceuticals | For profit | MKTG | Feb 27, 2017 |
| Taro Pharmaceuticals | For profit | MKTG | Feb 27, 2017 |
| Taro Pharmaceuticals | For profit | SYN | Feb 27, 2017 |
| Teva | For profit | MKTG | Dec 17, 1975 |
| Upsher-Smith Laboratories | For profit | MKTG | Dec 19, 1975 |
| Upsher-Smith Laboratories | For profit | SYN | Jan 25, 1983 |
| Vintage | For profit | MKTG | Jul 21, 2014 |
| Vitarine | For profit | MKTG | — |
| Watson Pharmaceuticals | For profit | MKTG | May 20, 1976 |
| Wes Pharma Inc | For profit | MKTG | Jun 16, 2020 |
| Wockhardt | For profit | MKTG | Dec 22, 1988 |
| Wockhardt | For profit | SYN | Jun 7, 1985 |
| Wyeth | For profit | NDA | Aug 23, 1957 |
| Wyeth | For profit | NDA2 | Aug 23, 1957 |
| Xttrium Laboratories | For profit | MKTG | Jun 7, 1985 |