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| Trade names | Hyprenan |
| Other names | CGP-7760B; CGP-7760/B; H-133/22; IHP |
| Routes of administration | Oral,IV |
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| ECHA InfoCard | 100.055.246 |
| Chemical and physical data | |
| Formula | C12H19NO3 |
| Molar mass | 225.288 g·mol−1 |
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Prenalterol, sold under the brand nameHyprenan, is asympathomimetic agent andcardiac stimulant which acts as aβ1-adrenergic receptorpartial agonist and is used in the treatment ofheart failure.[1][2][3][4][5] It hasselectivity for the β1-adrenergic receptor.[1][2][3][4] Its partial agonist activity orintrinsic sympathomimetic activity is about 60%.[6] It is said to have much greater impact onmyocardial contractility than onheart rate.[4] The drug has been marketed inDenmark,Norway, andSweden.[2]
Prenalterol exhibits adrenergic agonist activity in spite of an interposed oxymethylene group. Thestereospecific synthesis devised for this molecule relies on the fact that the side chain is very similar inoxidation state to that of a sugar.[7][8]
Condensation ofmonobenzone (2) with the epoxide derived from α-D-glucofuranose[9] affords the glycosylated derivative (3). Hydrolytic removal of theacetonide protecting groups[10] followed by cleavage of the sugar withperiodate gives aldehyde (4). This is reduced to theglycol by means ofNaBH4 and the terminal alcohol is converted to themesylate (5). Displacement of theleaving group withisopropylamine followed by hydrogenolytic removal of theO-benzyl ether affords theβ1-adrenergic selective adrenergic agonist prenalterol (6).
Several preparations of the racemic mixture have been reported.[11][12][13][14][15]