Befunolol

Befunolol
	File:Befunolol.svg
Clinical data
Trade names	Benfuran, Bentos, Betaclar, Glauconex
AHFS/Drugs.com	International Drug Names
ATC code	S01ED06 (WHO) ;
Identifiers
	IUPAC name (RS)-1-{7-[2-hydroxy-3-(propan-2-ylamino)propoxy]- 1-benzofuran-2-yl}ethanone;
CAS Number	39552-01-7 check;
PubChem CID	2309;
DrugBank	DB09013 check;
ChemSpider	2219 check;
UNII	418546MT3A;
KEGG	D07496 check;
ChEMBL	ChEMBL153984 check;
E number	{{#property:P628}}
CompTox Dashboard (EPA)	{{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).;
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C16H21NO4
Molar mass	291.347 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(c2oc1c(OCC(O)CNC(C)C)cccc1c2)C;
	InChI InChI=1S/C16H21NO4/c1-10(2)17-8-13(19)9-20-14-6-4-5-12-7-15(11(3)18)21-16(12)14/h4-7,10,13,17,19H,8-9H2,1-3H3 check; Key:ZPQPDBIHYCBNIG-UHFFFAOYSA-N check;

Befunolol (INN) is a beta blocker with intrinsic sympathomimetic activity used in the management of open-angle glaucoma.^[1] It also acts as a β adrenoreceptor partial agonist.^[2]^[3] Befunolol was introduced in Japan in 1983 by Kakenyaku Kako Co. under the trade name Bentos.^[4]

Synthesis

The first reported synthesis of befunolol in 1974 used a benzofuran derivative (4) with epichlorohydrin and then isopropylamine to add the sidechain which was known to produce beta blockers, by analogy with drugs discovered by Imperial Chemical Industries, such as propanolol.^[5] The requisite intermediate was synthesized from ortho-vanillin (1) by a condensation reaction with chloroacetone (2) in the presence of potassium hydroxide, giving 2-acetyl-7-methoxybenzofuran (3), which was demethylated using hydrobromic acid.^[6]^[7]^[8]

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