Steroidal, Aldosterone Antagonists: Increased selectivity of 9α,11‐epoxy derivatives

Grob, J.; Boillaz, Michel; Schmidlin, Julius; Wehrli, H.; Wieland, P.; Fuhrer, H.; Rihs, Grety; Joss, Urs R.; Gasparo, Marc de; Haenni, H; Ramjoué, Hans Peter; Whitebread, Steven; Kalvoda, J.

doi:10.1002/hlca.19970800220

Cited by 24 publications

(20 citation statements)

References 19 publications

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“…The C7-C8-C23-O6 torsion angle is 16.2 (5) , leading to a shorter O6Á Á ÁC7 contact of 2.706 (6) Å . These structural features are identical with those found in the crystal structure of eplerenone dichloromethane solvate (Grob et al, 1997).…”

Section: Commentsupporting

confidence: 80%

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Eplerenone tetrahydrofuran solvate

Yang

Yuan

et al. 2007

Acta Cryst E

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Section: Commentsupporting

confidence: 80%

“…A microcrystalline powder sample of eplerenone was prepared in the manner reported by Grob et al (1997). Single crystals of (I) were obtained from a THF solution of eplerenone.…”

Section: Methodsmentioning

confidence: 99%

Eplerenone tetrahydrofuran solvate

Yang

Yuan

et al. 2007

Acta Cryst E

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“…The C23-ester group forms an intra-molecular C -H•••O hydrogen bond with the adjacent C14-methine group (Table 1). This structural feature is also found in the crystal structure of eplerenone dichloromethane solvate (Grob et al, 1997).…”

Section: S1 Commentsupporting

confidence: 64%

“…A microcrystalline powder sample of eplerenone was prepared in the manner reported by Grob et al (1997). Single crystals of the title compound were obtained from an ethanol solution of eplerenone.…”

Section: S2 Experimentalmentioning

confidence: 99%

Eplerenone ethanol solvate

Yang

Yuan

et al. 2008

Acta Cryst E

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Eplerenone [systematic name: 7α-(methoxycarbonyl)-3-oxo-9α,11-epoxy-17α-pregn-4-ene-21,17-carbolactone], an aldosterone receptor antagonist, crystallizes from ethanol as a monosolvate, C24H30O6·C2H6O. The eplerenone molecule has two five-membered rings, three six-membered rings and one three-membered ring. Both five-membered rings display envelope conformations, while the three six-membered rings assume envelope (cyclohexene), half-chair (cyclohexane sharing one edge with epoxy) and chair (other cyclohexane) conformations. The solvent molecule is disordered equally over two sites. It is linked to the eplerenone molecule by hydrogen bonds.

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“…), but spironolactone is certainly recognized as a component of the therapy of primary aldosteronism [48]. More specific aldosterone receptor antagonists are currently in development [49], but will not be of any value in treating Liddle's syndrome. If renal function is normal, and dietary K ϩ intake is not excessive, there should not be an untoward incidence of hyperkalemia in patients with low renin hypertension who are treated with K ϩ -sparing diuretics, but monitoring of the serum electrolytes is worthwhile.…”

Section: Treatment Of Liddle's Syndromementioning

confidence: 99%

Liddle�s Syndrome: Genetics and Mechanisms of Na<sup>+</sup> Channel Defects

Warnock¹

2001

Contributions to Nephrology

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Liddle's syndrome is an extreme example of low renin, volume-expanded hypertension. Great strides have been made in understanding the monogenic forms of low renin hypertension [1]. We now have much better knowledge of the underlying pathophysiology of glucocorticoid-remediable aldosteronism [2], Liddle's syndrome [3], and the apparent mineralocorticoid excess syndrome [4]. In general, inappropriate renal Na ϩ retention with subsequent volume expansion, low plasma renin activity and hypertension are the consequences of inappropriate mineralocorticoid excess, or in the case of 'pseudoaldosteronism', apparent mineralocorticoid excess which results from constitutive activation of the amiloride-sensitive epithelial Na ϩ channel (ENaC) in the terminal nephron segments.Liddle's syndrome is a rare form of autosomal dominant hypertension with early penetrance and impressive cardiovascular sequelae. The basic features of this syndrome were described in a large kindred from Alabama by Grant Liddle and co-workers [5] in 1963. In addition to severe hypertension, many of the patients had overt hypokalemia. Despite a clinical presentation typical of primary aldosteronism, the actual rates of aldosterone excretion were markedly suppressed, accounting for the descriptive term 'pseudoaldosteronism'. Liddle et al. [5] found that spironolactone, a mineralocorticoid antagonist, did not have any discernible effect, while triamterene normalized the blood pressure, reversed the renal potassium wasting and corrected the hypokalemia as long as the subjects restricted their dietary salt intake. These findings were correctly interpreted as indicating an intrinsic renal defect in the regulation of salt absorption rather than the effects on the distal tubule of some unidentified mineralocorticoid [5].

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Steroidal, Aldosterone Antagonists: Increased selectivity of 9α,11‐epoxy derivatives

Cited by 24 publications

References 19 publications

Eplerenone tetrahydrofuran solvate

Eplerenone tetrahydrofuran solvate

Eplerenone ethanol solvate

Liddle�s Syndrome: Genetics and Mechanisms of Na<sup>+</sup> Channel Defects

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