bevantolol

{{Short description|Chemical compound}}

{{Drugbox

| verifiedrevid = 443421622

| IUPAC_name = (RS)-[2-(3,4-dimethoxyphenyl)ethyl][2-hydroxy-3-(3-methylphenoxy)propyl]amine

| image = Bevantolol.svg

| width = 240px

| chirality = Racemic mixture

| tradename =

| Drugs.com = {{drugs.com|international|bevantolol}}

| pregnancy_AU =

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| legal_AU =

| legal_CA =

| legal_UK =

| legal_US =

| legal_status =

| routes_of_administration = Oral

| bioavailability =

| protein_bound =

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| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 59170-23-9

| ATC_prefix = C07

| ATC_suffix = AB06

| ATC_supplemental =

| PubChem = 2372

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB01295

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 2282

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 34ZXW6ZV21

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 238698

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 314010

| synonyms =

| C=20 | H=27 | N=1 | O=4

| SMILES = O(c1ccc(cc1OC)CCNCC(O)COc2cc(ccc2)C)C

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C20H27NO4/c1-15-5-4-6-18(11-15)25-14-17(22)13-21-10-9-16-7-8-19(23-2)20(12-16)24-3/h4-8,11-12,17,21-22H,9-10,13-14H2,1-3H3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = HXLAFSUPPDYFEO-UHFFFAOYSA-N

}}

Bevantolol (INN) was a drug candidate for angina and hypertension that acted as both a beta blocker and a calcium channel blocker.{{cite journal | vauthors = Frishman WH, Goldberg RJ, Benfield P | title = Bevantolol. A preliminary review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy in hypertension and angina pectoris | journal = Drugs | volume = 35 | issue = 1 | pages = 1–21 | date = January 1988 | pmid = 2894292 | doi = 10.2165/00003495-198835010-00001 }}{{cite journal | vauthors = Vaughan Williams EM | title = Bevantolol: a beta-1 adrenoceptor antagonist with unique additional actions | journal = Journal of Clinical Pharmacology | volume = 27 | issue = 7 | pages = 450–60 | date = July 1987 | pmid = 2888789 | doi = 10.1002/j.1552-4604.1987.tb03049.x | s2cid = 72749127 }} It was discovered and developed by Warner-Lambert{{cite book|last1=McPherson|first1=Edwin M. | name-list-style = vanc |title=Pharmaceutical Manufacturing Encyclopedia.|date=2007|publisher=Elsevier|location=Burlington|isbn=9780815518563|pages=618–619|edition=3rd|url=https://books.google.com/books?id=_J2ti4EkYpkC&pg=PA618}} but in January 1989 the company announced that it had withdrawn the New Drug Application; the company's chairman said: "Who needs the 30th beta blocker?"{{cite news|title=Warner-Lambert Pipeline Narrowed to 40 Active Research Compounds|url=https://pink.pharmamedtechbi.com/PS015015/WARNERLAMBERT-PIPELINE-NARROWED-TO-40-ACTIVE-RESEARCH-COMPOUNDS-ACCUPRIL-QUINAPRIL-NDA-SUBMITTED-JAN-25-80-MIL-BUDGETTED-FOR-CV-WORK-IN-1989|work=Pink Sheet|date=30 January 1989}} {{as of|2016}} it wasn't marketed in the US, UK, or Europe and the authors of a Cochrane review could find no product monograph for it.{{cite journal | vauthors = Wong GW, Boyda HN, Wright JM | title = Blood pressure lowering efficacy of beta-1 selective beta blockers for primary hypertension | journal = The Cochrane Database of Systematic Reviews | volume = 3 | pages = CD007451 | date = March 2016 | issue = 4 | pmid = 26961574 | pmc = 6486283 | doi = 10.1002/14651858.CD007451.pub2 }}