Bevantolol

Chemical compound

C07AB06 (WHO)

Identifiers

IUPAC name

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

CAS Number

59170-23-9^Y

PubChem CID

2372

DrugBank

DB01295^Y

ChemSpider

2282^Y

UNII

34ZXW6ZV21

ChEBI

CHEBI:238698^Y

ChEMBL

ChEMBL314010^Y

CompTox Dashboard (EPA)

DTXSID70860597

Chemical and physical dataFormulaC₂₀H₂₇NO₄Molar mass345.439 g·mol⁻¹3D model (JSmol)

Interactive image

ChiralityRacemic mixture

SMILES

O(c1ccc(cc1OC)CCNCC(O)COc2cc(ccc2)C)C

InChI

InChI=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^Y
Key:HXLAFSUPPDYFEO-UHFFFAOYSA-N^Y

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Bevantolol (INN) was a drug candidate for angina and hypertension that acted as both a beta blocker and a calcium channel blocker.^[1]^[2] It was discovered and developed by Warner-Lambert^[3] but in January 1989 the company announced that it had withdrawn the New Drug Application; the company's chairman said: "Who needs the 30th beta blocker?"^[4] As of 2016^[update] it wasn't marketed in the US, UK, or Europe and the authors of a Cochrane review could find no product monograph for it.^[5]

References

^ Frishman WH, Goldberg RJ, Benfield P (January 1988). "Bevantolol. A preliminary review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy in hypertension and angina pectoris". Drugs. 35 (1): 1–21. doi:10.2165/00003495-198835010-00001. PMID 2894292.
^ Vaughan Williams EM (July 1987). "Bevantolol: a beta-1 adrenoceptor antagonist with unique additional actions". Journal of Clinical Pharmacology. 27 (7): 450–60. doi:10.1002/j.1552-4604.1987.tb03049.x. PMID 2888789. S2CID 72749127.
^ McPherson EM (2007). Pharmaceutical Manufacturing Encyclopedia (3rd ed.). Burlington: Elsevier. pp. 618–619. ISBN 9780815518563.
^ "Warner-Lambert Pipeline Narrowed to 40 Active Research Compounds". Pink Sheet. 30 January 1989.
^ Wong GW, Boyda HN, Wright JM (March 2016). "Blood pressure lowering efficacy of beta-1 selective beta blockers for primary hypertension". The Cochrane Database of Systematic Reviews. 3 (4): CD007451. doi:10.1002/14651858.CD007451.pub2. PMC 6486283. PMID 26961574.