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Bromazine

From Wikipedia, the free encyclopedia
Chemical compound
Not to be confused withPromazine.
Pharmaceutical compound
Bromazine
Clinical data
Trade namesAmbodryl, Ambrodil, Deserol
Other namesBromodiphenhydramine; Bromdiphenhydramine
MedlinePlusa682065
Routes of
administration
Oral
ATC code
Pharmacokinetic data
BioavailabilityHigh
Protein binding96%
MetabolismMostlyhepatic (CYP-mediated), alsorenal
Eliminationhalf-life1 to 4 hours
Identifiers
  • 2-[(4-Bromophenyl)-phenylmethoxy]-N,N-dimethylethanamine
CAS Number
PubChemCID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.003.854Edit 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
 ☒NcheckY (what is this?)  (verify)

Bromazine, sold under the brand namesAmbodryl,Ambrodil, andDeserol among others, also known asbromodiphenhydramine, is anantihistamine andanticholinergic medication of theethanolamine class.[1][2][3][4][5] It is ananalogue ofdiphenhydramine with abrominesubstitution on one of thephenyl rings.[1][2]

Synthesis

[edit]
Synthesis:[6] Patent:[7]

Grignard reaction betweenphenylmagnesium bromide and para-bromobenzaldehyde [1122-91-4] (1) gives p-bromobenzhydrol [29334-16-5] (2). Halogenation withacetyl bromide in benzene solvent gives p-bromo-benzhydrylbromide [18066-89-2] (3). Finally, etherification withdeanol completed the synthesis of Bromazine (4).

Side effects

[edit]

Continuous and/or cumulative use ofanticholinergic medications, including first-generation antihistamines, is associated with higher risk forcognitive decline anddementia in elderly people.[8][9]

References

[edit]
  1. ^abElks 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.
  2. ^abSwiss Pharmaceutical Society (2000). Swiss Pharmaceutical Society (ed.).Index Nominum 2000: International Drug Directory. Taylor & Francis. pp. 134–.ISBN 978-3-88763-075-1.
  3. ^Baker CE (1974).Physicians' Desk Reference (28th ed.). Oradell, NJ: Medical Economics Company. pp. 1076, 1081.
  4. ^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.
  5. ^Maclaren WR, Bruff WC, Eisenberg BC, Weiner H, Martin WH (1955). "A clinical comparison of carbinoxamine maleate, tripelennamine hydrochloride, and bromodiphenhydramine hydrochloride in treating allergic symptoms".Annals of Allergy.13 (3):307–312.PMID 14377226.
  6. ^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.
  7. ^US 2527963, Rieveschl Jr G, "Beta-dimethylamino-ethyl rho-halobenzhydryl ethers and their salts", issued 31 October 1950, assigned to Parke Davis & Co. 
  8. ^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.
  9. ^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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