From Wikipedia, the free encyclopedia
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]
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
^
a
b 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 .
^
a
b Swiss Pharmaceutical Society (2000). Swiss Pharmaceutical Society (ed.).
Index Nominum 2000: International Drug Directory . Taylor & Francis. pp. 134–.
ISBN
978-3-88763-075-1 .
^ Baker CE (1974). Physicians' Desk Reference (28th ed.). Oradell, NJ 07649: Medical Economics Company. pp. 1076, 1081. {{
cite book }}
: CS1 maint: location (
link )
^ 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 .
^ 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 .
^ 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 .
H1
Agonists Antagonists
Others:
Atypical antipsychotics (e.g.,
aripiprazole ,
asenapine ,
brexpiprazole ,
brilaroxazine ,
clozapine ,
iloperidone ,
olanzapine ,
paliperidone ,
quetiapine ,
risperidone ,
ziprasidone ,
zotepine )
Phenylpiperazine
antidepressants (e.g.,
hydroxynefazodone ,
nefazodone ,
trazodone ,
triazoledione )
Tetracyclic antidepressants (e.g.,
amoxapine ,
loxapine ,
maprotiline ,
mianserin ,
mirtazapine ,
oxaprotiline )
Tricyclic antidepressants (e.g.,
amitriptyline ,
butriptyline ,
clomipramine ,
desipramine ,
dosulepin (dothiepin) ,
doxepin ,
imipramine ,
iprindole ,
lofepramine ,
nortriptyline ,
protriptyline ,
trimipramine )
Typical antipsychotics (e.g.,
chlorpromazine ,
flupenthixol ,
fluphenazine ,
loxapine ,
perphenazine ,
prochlorperazine ,
thioridazine ,
thiothixene )
H2
H3
H4
mAChRs Tooltip Muscarinic acetylcholine receptors
Agonists
Antagonists
3-Quinuclidinyl benzilate
4-DAMP
Aclidinium bromide (
+formoterol )
Abediterol
AF-DX 250
AF-DX 384
Ambutonium bromide
Anisodamine
Anisodine
Antihistamines (first-generation) (e.g.,
brompheniramine ,
buclizine ,
captodiame ,
chlorphenamine (chlorpheniramine) ,
cinnarizine ,
clemastine ,
cyproheptadine ,
dimenhydrinate ,
dimetindene ,
diphenhydramine ,
doxylamine ,
meclizine ,
mequitazine ,
perlapine ,
phenindamine ,
pheniramine ,
phenyltoloxamine ,
promethazine ,
propiomazine ,
triprolidine )
AQ-RA 741
Atropine
Atropine methonitrate
Atypical antipsychotics (e.g.,
clozapine ,
fluperlapine ,
olanzapine (
+fluoxetine ),
rilapine ,
quetiapine ,
tenilapine ,
zotepine )
Benactyzine
Benzatropine (benztropine)
Benzilone
Benzilylcholine mustard
Benzydamine
BIBN 99
Biperiden
Bornaprine
Camylofin
CAR-226,086
CAR-301,060
CAR-302,196
CAR-302,282
CAR-302,368
CAR-302,537
CAR-302,668
Caramiphen
Cimetropium bromide
Clidinium bromide
Cloperastine
CS-27349
Cyclobenzaprine
Cyclopentolate
Darifenacin
DAU-5884
Desfesoterodine
Dexetimide
DIBD
Dicycloverine (dicyclomine)
Dihexyverine
Difemerine
Diphemanil metilsulfate
Ditran
Drofenine
EA-3167
EA-3443
EA-3580
EA-3834
Emepronium bromide
Etanautine
Etybenzatropine (ethybenztropine)
Fenpiverinium
Fentonium bromide
Fesoterodine
Flavoxate
Glycopyrronium bromide (
+beclometasone/formoterol ,
+indacaterol ,
+neostigmine )
Hexahydrodifenidol
Hexahydrosiladifenidol
Hexbutinol
Hexocyclium
Himbacine
HL-031,120
Homatropine
Imidafenacin
Ipratropium bromide (
+salbutamol )
Isopropamide
J-104,129
Hyoscyamine
Mamba toxin 3
Mamba toxin 7
Mazaticol
Mebeverine
Meladrazine
Mepenzolate
Methantheline
Methoctramine
Methylatropine
Methylhomatropine
Methylscopolamine
Metixene
Muscarinic toxin 7
N-Ethyl-3-piperidyl benzilate
N-Methyl-3-piperidyl benzilate
Nefopam
Octatropine methylbromide (anisotropine methylbromide)
Orphenadrine
Otenzepad (AF-DX 116)
Otilonium bromide
Oxapium iodide
Oxitropium bromide
Oxybutynin
Oxyphencyclimine
Oxyphenonium bromide
PBID
PD-102,807
PD-0298029
Penthienate
Pethidine
pFHHSiD
Phenglutarimide
Phenyltoloxamine
Pipenzolate bromide
Piperidolate
Pirenzepine
Piroheptine
Pizotifen
Poldine
Pridinol
Prifinium bromide
Procyclidine
Profenamine (ethopropazine)
Propantheline bromide
Propiverine
Quinidine
3-Quinuclidinyl thiochromane-4-carboxylate
Revefenacin
Rociverine
RU-47,213
SCH-57,790
SCH-72,788
SCH-217,443
Scopolamine (hyoscine)
Scopolamine butylbromide (hyoscine butylbromide)
Silahexacyclium
Sofpironium bromide
Solifenacin
SSRIs Tooltip Selective serotonin reuptake inhibitors (e.g.,
femoxetine ,
paroxetine )
Telenzepine
Terodiline
Tetracyclic antidepressants (e.g.,
amoxapine ,
maprotiline ,
mianserin ,
mirtazapine )
Tiemonium iodide
Timepidium bromide
Tiotropium bromide
Tiquizium bromide
Tofenacin
Tolterodine
Tricyclic antidepressants (e.g.,
amitriptyline (
+perphenazine ),
amitriptylinoxide ,
butriptyline ,
cidoxepin ,
clomipramine ,
desipramine ,
desmethyldesipramine ,
dibenzepin ,
dosulepin (dothiepin) ,
doxepin ,
imipramine ,
lofepramine ,
nitroxazepine ,
northiaden (desmethyldosulepin) ,
nortriptyline ,
protriptyline ,
quinupramine ,
trimipramine )
Tridihexethyl
Trihexyphenidyl
Trimebutine
Tripitamine (tripitramine)
Tropacine
Tropatepine
Tropicamide
Trospium chloride
Typical antipsychotics (e.g.,
chlorpromazine ,
chlorprothixene ,
cyamemazine (cyamepromazine) ,
loxapine ,
mesoridazine ,
thioridazine )
Umeclidinium bromide (
+vilanterol )
WIN-2299
Xanomeline
Zamifenacin
Precursors (and
prodrugs )