Bromazine

Chemical compound From Wikipedia, the free encyclopedia

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]

Trade namesAmbodryl, Ambrodil, Deserol
Other namesBromodiphenhydramine; Bromdiphenhydramine
Quick facts Clinical data, Trade names ...
Bromazine
Clinical data
Trade namesAmbodryl, Ambrodil, Deserol
Other namesBromodiphenhydramine; Bromdiphenhydramine
MedlinePlusa682065
Routes of
administration
Oral
ATC code
Pharmacokinetic data
BioavailabilityHigh
Protein binding96%
MetabolismMostly hepatic (CYP-mediated), also renal
Elimination half-life1 to 4 hours
Identifiers
  • 2-[(4-Bromophenyl)-phenylmethoxy]-N,N-dimethylethanamine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.003.854 Edit this at Wikidata
Chemical and physical data
FormulaC17H20BrNO
Molar mass334.257 g·mol−1
3D model (JSmol)
  • Brc1ccc(cc1)C(OCCN(C)C)c2ccccc2
  • InChI=1S/C17H20BrNO/c1-19(2)12-13-20-17(14-6-4-3-5-7-14)15-8-10-16(18)11-9-15/h3-11,17H,12-13H2,1-2H3 checkY
  • Key:NUNIWXHYABYXKF-UHFFFAOYSA-N checkY
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Synthesis

Synthesis:[6] Patent:[7]

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).

Side effects

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]

References

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