| Revision as of 15:54, 10 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank', 'ChEMBL').← Previous edit |
Latest revision as of 16:07, 7 September 2024 edit undoJWBE (talk | contribs)Extended confirmed users10,127 edits removed Category:Bromobenzene derivatives; added Category:4-Bromophenyl compounds using HotCat |
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{{Short description|Chemical compound}} |
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{{Distinguish|Promazine}} |
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{{Drugbox |
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{{Drugbox |
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| verifiedrevid = 459983265 |
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| IUPAC_name = 2--''N'',''N''-dimethylethanamine |
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| verifiedrevid = 401934876 |
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| IUPAC_name = 2--''N'',''N''-dimethylethanamine |
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| image = Bromazine.svg |
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| image = Bromazine.svg |
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| width = |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| tradename = |
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| tradename = Ambodryl, Ambrodil, Deserol |
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| MedlinePlus = a682065 |
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| MedlinePlus = a682065 |
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| routes_of_administration = Oral |
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| routes_of_administration = ] |
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<!--Pharmacokinetic data--> |
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<!--Pharmacokinetic data--> |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| IUPHAR_ligand = 7132 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 1808-12-4 |
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| CAS_number = 1808-12-4 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 202J683U97 |
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| UNII = 202J683U97 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 59177 |
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| ChEBI = 59177 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = <!-- blanked - oldvalue: 1201245 --> |
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| ChEMBL = 1201245 |
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| synonyms = Bromodiphenhydramine; Bromdiphenhydramine |
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| C=17 | H=20 | Br=1 | N=1 | O=1 |
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| molecular_weight = 334.251 g/mol |
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<!--Chemical data--> |
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| smiles = Brc1ccc(cc1)C(OCCN(C)C)c2ccccc2 |
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| C=17 | H=20 | Br=1 | N=1 | O=1 |
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| InChI = 1/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 |
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| SMILES = Brc1ccc(cc1)C(OCCN(C)C)c2ccccc2 |
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| InChIKey = NUNIWXHYABYXKF-UHFFFAOYAG |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 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 |
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| StdInChI = 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 |
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'''Bromazine''', sold under the brand names '''Ambodryl''', '''Ambrodil''', and '''Deserol''' among others, also known as '''bromodiphenhydramine''', is an ] and ] medication of the ] class.<ref name="Elks2014">{{cite book | veditors = Elks J | date = 14 November 2014 | title = The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies | publisher = Springer | pages = 177– | isbn = 978-1-4757-2085-3 | oclc = 1058412474 | url = https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA177}}</ref><ref name="SwissPharmaceuticalSociety2000">{{cite book | editor = Swiss Pharmaceutical Society | author = Swiss Pharmaceutical Society | date = 2000 | title = Index Nominum 2000: International Drug Directory | publisher = Taylor & Francis | pages = 134– | isbn = 978-3-88763-075-1 | url = https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA134}}</ref><ref name="PDR1974">{{cite book| vauthors = Baker CE |title=Physicians' Desk Reference|date=1974|publisher=Medical Economics Company|location=Oradell, NJ 07649|pages=1076, 1081|edition=28th}}</ref><ref name="pmid23173575">{{cite journal | vauthors = Kalpaklioglu F, Baccioglu A | title = Efficacy and safety of H1-antihistamines: an update | journal = Anti-Inflammatory & Anti-Allergy Agents in Medicinal Chemistry | volume = 11 | issue = 3 | pages = 230–237 | date = 2012 | pmid = 23173575 | doi = 10.2174/1871523011202030230 }}</ref><ref name="pmid14377226">{{cite journal | vauthors = Maclaren WR, Bruff WC, Eisenberg BC, Weiner H, Martin WH | title = A clinical comparison of carbinoxamine maleate, tripelennamine hydrochloride, and bromodiphenhydramine hydrochloride in treating allergic symptoms | journal = Annals of Allergy | volume = 13 | issue = 3 | pages = 307–312 | year = 1955 | pmid = 14377226 }}</ref> It is an ] of ] with a ] ] on one of the ]s.<ref name="Elks2014" /><ref name="SwissPharmaceuticalSociety2000" /> |
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'''Bromazine''' ('''Amrodyl'''), also known as '''bromodiphenhydramine''', is an ] and ]. |
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==Synthesis== |
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] |
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Grignard reaction between ] and para-bromobenzaldehyde ('''1''') gives p-bromobenzhydrol ('''2'''). Halogenation with ] in benzene solvent gives p-bromo-benzhydrylbromide ('''3'''). Finally, etherification with ] completed the synthesis of Bromazine ('''4'''). |
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==Side effects== |
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Continuous and/or cumulative use of ] medications, including first-generation antihistamines, is associated with higher risk for ] and ] in elderly people.<ref>{{cite journal | vauthors = Gray SL, Anderson ML, Dublin S, Hanlon JT, Hubbard R, Walker R, Yu O, Crane PK, Larson EB | display-authors = 6 | title = Cumulative use of strong anticholinergics and incident dementia: a prospective cohort study | journal = JAMA Internal Medicine | volume = 175 | issue = 3 | pages = 401–407 | date = March 2015 | pmid = 25621434 | pmc = 4358759 | doi = 10.1001/jamainternmed.2014.7663 | author5-link = Rebecca Hubbard }}</ref><ref>{{cite journal | vauthors = Carrière I, Fourrier-Reglat A, Dartigues JF, Rouaud O, Pasquier F, Ritchie K, Ancelin ML | title = Drugs with anticholinergic properties, cognitive decline, and dementia in an elderly general population: the 3-city study | journal = Archives of Internal Medicine | volume = 169 | issue = 14 | pages = 1317–1324 | date = July 2009 | pmid = 19636034 | pmc = 2933398 | doi = 10.1001/archinternmed.2009.229 }}</ref> |
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== References == |
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== References == |
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{{Reflist|2}} |
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{{Reflist}} |
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{{Cholinergics}} |
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{{Antihistamines}} |
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{{Histamine receptor modulators}} |
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{{Histaminergics}} |
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{{Muscarinic acetylcholine receptor modulators}} |
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{{Amine-stub}} |
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{{respiratory-system-drug-stub}} |
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{{Respiratory-system-drug-stub}} |
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