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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 ).
References
^ a b J. Elks, 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 (28 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-Inflamm Anti-Allergy Agents Med Chem . 11 (3): 230–7. 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): 307–12. PMID 14377226 .
^ Ahmadi, Abbas; Khalili, Mohsen; Hajikhani, Ramin; Safari, Narjes; Nahri-Niknafs, Babak (2011). "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.
^ Jr George Rieveschl, US2527963 (1950 to Parke Davis & Co).
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 )