Bevantolol

Bevantolol
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral
ATC code	C07AB06 (WHO) ;
Identifiers
	IUPAC name (RS)-[2-(3,4-dimethoxyphenyl)ethyl][2-hydroxy-3-(3-methylphenoxy)propyl]amine;
CAS Number	59170-23-9 ;
PubChem CID	2372;
DrugBank	DB01295 ;
ChemSpider	2282 ;
UNII	34ZXW6ZV21;
ChEBI	CHEBI:238698 ;
ChEMBL	ChEMBL314010 ;
CompTox Dashboard (EPA)	DTXSID70860597 ;
Chemical and physical data
Formula	C20H27NO4
Molar mass	345.439 g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Racemic 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 ; Key:HXLAFSUPPDYFEO-UHFFFAOYSA-N ;
	(verify)

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It was discovered and developed by Warner-Lambert^[3] but in January 1989 the company announced that it had withdrawn the New Drug Application; the company's chairman said: "Who needs the 30th beta blocker?"^[4] As of 2016^[update] it wasn't marketed in the US, UK, or Europe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]

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[1] [1]
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.

[2] [2]
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.

[3] [3]
McPherson EM (2007). Pharmaceutical Manufacturing Encyclopedia (3rd ed.). Burlington: Elsevier. pp. 618–619. ISBN 9780815518563.

[4] [4]
"Warner-Lambert Pipeline Narrowed to 40 Active Research Compounds". Pink Sheet. 30 January 1989.

[5] [5]
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.

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Bevantolol

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References

Clinical data

AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	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 data
Formula	C₂₀H₂₇NO₄
Molar mass	345.439 g·mol⁻¹
3D model (JSmol)	Interactive image
Chirality	Racemic 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
(verify)