Eplerenone ethanol solvate

Abstract

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.

Synthesis and Physicochemical Characterization of the Process-Related Impurities of Eplerenone, an Antihypertensive Drug

“…Eplerenone contains sensitive 9,11α-epoxide, 17α-γ-lactone and 7α-carbomethoxy moieties that, depending on the conditions, may hydrolyze or epimerize to afford degradation or epimerization products [ 9 , 10 , 11 , 12 , 13 ]. The SCXRD structure of eplerenone confirms the relative cis configuration of the 9α,11α-epoxide ring and the 7α-carbomethoxy substituent [ 14 , 15 , 16 , 17 ]. Manufacture of eplerenone is always accompanied by side reactions leading to the unwanted impurities that vary with the different starting materials and reaction conditions used.…”

Polymorphism Solvatomorphism 2008

“…The 2008 literature also contained a number of additional reports on the structures and properties of solvatomorphs for various compounds having pharmaceutical interest, and some details of these have been summarized in Table 2 126–141…”

Thermodynamic Analysis of Eplerenone in 13 Pure Solvents at Temperatures from 283.15 to 323.15 K

“…Eplerenone (EP) is a novel selective aldosterone receptor antagonist first developed by Pfizer, which was initially marketed in the US in 2002 for the treatment of hypertension and heart failure. − EP, CAS No. 107724-20-9, the systematic name of 9α,11-epoxy-7α-methoxycarbonyl-3-oxo-17α-pregn-4-ene-21,17-carbolactonean, molecular formula: C 24 H 30 O 6 , molecular weight: 414.49 g·mol –1 , is an odorless, white or off-white crystal powder, and its chemical structure and three-dimensional (3D) structure are depicted in Figure . , …”

“…107724-20-9, the systematic name of 9α,11-epoxy-7α-methoxycarbonyl-3-oxo-17α-pregn-4ene-21,17-carbolactonean, molecular formula: C 24 H 30 O 6 , molecular weight: 414.49 g•mol −1 , is an odorless, white or offwhite crystal powder, and its chemical structure and threedimensional (3D) structure are depicted in Figure 1. 4,5 As a novel selective aldosterone receptor antagonist, EP has stronger antagonistic effects on aldosterone than spironolactone. Additionally, it exhibits minimal affinity for androgen and progesterone receptors, leading to reduce adverse reactions.…”

“…107724-20-9, the systematic name of 9α,11-epoxy-7α-methoxycarbonyl-3-oxo-17α-pregn-4-ene-21,17-carbolactonean, molecular formula: C 24 H 30 O 6 , molecular weight: 414.49 g·mol –1 , is an odorless, white or off-white crystal powder, and its chemical structure and three-dimensional (3D) structure are depicted in Figure 1 . 4 , 5 …”