bufenadrine

{{Short description|Chemical compound}}

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| image = Bufenadrine.svg

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| class = Antiemetic; Antihistamine; Anticholinergic; Antiparkinsonian agent

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| CAS_number = 604-74-0

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| PubChem = 21916

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| ChemSpiderID = 20600

| UNII = 9Y0T619B3U

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| ChEMBL = 2104614

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| synonyms = B.S. 6534; BS-6534; 2-tert-Butyldiphenhydramine

| IUPAC_name = 2-[(2-tert-butylphenyl)-phenylmethoxy]-N,N-dimethylethanamine

| C=21 | H=29 | N=1 | O=1

| SMILES = CC(C)(C)C1=CC=CC=C1C(C2=CC=CC=C2)OCCN(C)C

| StdInChI = 1S/C21H29NO/c1-21(2,3)19-14-10-9-13-18(19)20(23-16-15-22(4)5)17-11-7-6-8-12-17/h6-14,20H,15-16H2,1-5H3

| StdInChIKey = OGNRRAFRDFGFKA-UHFFFAOYSA-N

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Bufenadrine ({{Abbrlink|INN|International Nonproprietary Name}}; developmental code name B.S. 6534), also known as 2-tert-butyldiphenhydramine, is a drug described as an antiemetic, antihistamine, anticholinergic, and antiparkinsonian agent which was never marketed.{{cite book | vauthors = Elks J | title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies | publisher=Springer US | year=2014 | isbn=978-1-4757-2085-3 | url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA186 | access-date=17 October 2024 | page=186}}{{cite book | vauthors = Eichelbaum MF, Testa B, Somogyi A | title=Stereochemical Aspects of Drug Action and Disposition | publisher=Springer Berlin Heidelberg | series=Handbook of Experimental Pharmacology | year=2012 | isbn=978-3-642-55842-9 | url=https://books.google.com/books?id=0U_xCAAAQBAJ&pg=PA422 | access-date=17 October 2024 | page=422}}{{cite book | vauthors = Ariëns EJ | title=Drug Design: Medicinal Chemistry: A Series of Monographs, Vol. 6 | publisher=Academic Press | issue=v. 6 | year=2013 | isbn=978-1-4832-1608-9 | url=https://books.google.com/books?id=PQwlBQAAQBAJ&pg=PA12 | access-date=17 October 2024 | page=12}}{{cite book | title=Pharmaceutical Manufacturing Encyclopedia | publisher=William Andrew Publishing | series=Volumes 1-4 | year=2013 | isbn=978-0-8155-1856-3 | url=https://books.google.com/books?id=_J2ti4EkYpkC&pg=PA704 | access-date=17 October 2024 | pages=704–705}} It is the 2-tert-butyl analogue of diphenhydramine. The drug was found to produce stereoselective hepatotoxicity in animals and this led to the discontinuation of its development.{{cite journal | vauthors = Hespe W, Mulder D, van Eeken CJ | title = Differences in metabolic behavior and liver toxicity between the optical isomers of bufenadrine hydrochloride, a substituted diphenhydramine, in the rat | journal = Acta Pharmacol Toxicol (Copenh) | volume = 31 | issue = 5 | pages = 369–379 | date = 1972 | pmid = 4678820 | doi = 10.1111/j.1600-0773.1972.tb03600.x | url = }} Bufenadrine was first described in the literature by 1967. Its {{Abbrlink|INN|International Nonproprietary Name}} suffix "-drine" is generally for sympathomimetics but bufenadrine itself is not actually a sympathomimetic or related agent.{{cite book | chapter = -drine sympathomimetics | title = The use of stems in the selection of International Nonproprietary Names (INN) for pharmaceutical substances 2018 (Stem Book 2018) | chapter-url = https://cdn.who.int/media/docs/default-source/international-nonproprietary-names-(inn)/stembook-2018.pdf#page=95 | publisher = World Health Organization }}