Bromazine
Bromazine
Chemical compound
Bromazine, sold under the brand names Ambodryl, Ambrodil, and Deserol among others, also known as bromodiphenhydramine, is an antihistamine and anticholinergic medication of the ethanolamine class.[1][2][3][4][5] It is an analogue of diphenhydramine with a bromine substitution on one of the phenyl rings.[1][2]
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Trade names | Ambodryl, Ambrodil, Deserol |
Other names | Bromodiphenhydramine; Bromdiphenhydramine |
MedlinePlus | a682065 |
Routes of administration | Oral |
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Pharmacokinetic data | |
Bioavailability | High |
Protein binding | 96% |
Metabolism | Mostly hepatic (CYP-mediated), also renal |
Elimination half-life | 1 to 4 hours |
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ECHA InfoCard | 100.003.854 |
Chemical and physical data | |
Formula | C17H20BrNO |
Molar mass | 334.257 g·mol−1 |
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Grignard reaction between phenylmagnesium bromide and para-bromobenzaldehyde [1122-91-4] (1) gives p-bromobenzhydrol [29334-16-5] (2). Halogenation with acetyl bromide in benzene solvent gives p-bromo-benzhydrylbromide [18066-89-2] (3). Finally, etherification with deanol completed the synthesis of Bromazine (4).
Continuous and/or cumulative use of anticholinergic medications, including first-generation antihistamines, is associated with higher risk for cognitive decline and dementia in elderly people.[8][9]
- Elks J, ed. (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 177–. ISBN 978-1-4757-2085-3. OCLC 1058412474.
- Swiss Pharmaceutical Society (2000). Swiss Pharmaceutical Society (ed.). Index Nominum 2000: International Drug Directory. Taylor & Francis. pp. 134–. ISBN 978-3-88763-075-1.
- Kalpaklioglu F, Baccioglu A (2012). "Efficacy and safety of H1-antihistamines: an update". Anti-Inflammatory & Anti-Allergy Agents in Medicinal Chemistry. 11 (3): 230–237. doi:10.2174/1871523011202030230. PMID 23173575.
- Ahmadi A, Khalili M, Hajikhani R, Safari N, Nahri-Niknafs B (November 2012). "Anti-inflammatory effects of two new methyl and morpholine derivatives of diphenhydramine on rats". Medicinal Chemistry Research. 21 (11): 3532–3540. doi:10.1007/s00044-011-9891-y. S2CID 253644478.
- US 2527963, Rieveschl Jr G, "Beta-dimethylamino-ethyl rho-halobenzhydryl ethers and their salts", issued 31 October 1950, assigned to Parke Davis & Co.
- Gray SL, Anderson ML, Dublin S, Hanlon JT, Hubbard R, Walker R, et al. (March 2015). "Cumulative use of strong anticholinergics and incident dementia: a prospective cohort study". JAMA Internal Medicine. 175 (3): 401–407. doi:10.1001/jamainternmed.2014.7663. PMC 4358759. PMID 25621434.
- Carrière I, Fourrier-Reglat A, Dartigues JF, Rouaud O, Pasquier F, Ritchie K, Ancelin ML (July 2009). "Drugs with anticholinergic properties, cognitive decline, and dementia in an elderly general population: the 3-city study". Archives of Internal Medicine. 169 (14): 1317–1324. doi:10.1001/archinternmed.2009.229. PMC 2933398. PMID 19636034.
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