Bromazine

Not to be confused with Promazine.

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]

Bromazine

Clinical data
Trade names	Ambodryl, Ambrodil, Deserol
Other names	Bromodiphenhydramine; Bromdiphenhydramine
MedlinePlus	a682065
Routes of administration	Oral
ATC code	R06AA01 (WHO)
Pharmacokinetic data
Bioavailability	High
Protein binding	96%
Metabolism	Mostly hepatic (CYP-mediated), also renal
Elimination half-life	1 to 4 hours
Identifiers
IUPAC name 2-[(4-Bromophenyl)-phenylmethoxy]-N,N-dimethylethanamine
CAS Number	1808-12-4 Y 1808-12-4
PubChem CID	2444
IUPHAR/BPS	7132
DrugBank	DB01237 Y
ChemSpider	2350 Y
UNII	202J683U97
ChEBI	CHEBI:59177 Y
ChEMBL	ChEMBL1201245 N
CompTox Dashboard (EPA)	DTXSID6022688
ECHA InfoCard	100.003.854
Chemical and physical data
Formula	C17H20BrNO
Molar mass	334.257 g·mol−1
3D model (JSmol)	Interactive image
SMILES Brc1ccc(cc1)C(OCCN(C)C)c2ccccc2
InChI 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 Y Key:NUNIWXHYABYXKF-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

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

1. 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.
2. Swiss 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 07649: Medical Economics Company. pp. 1076, 1081.{{cite book}}: CS1 maint: location (link)
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.