This paper reports the crystal structure of the propanol solvate of 9 alpha-fluorocortisol acetate, which crystallizes in the monoclinic space group P21 [a = 7.470 (6), b = 14.78 (1), c = 12.310 (9), beta = 105.2 degrees, Z = 2, R = 0.061, and the tetragonal unsolvated crystal form (a = b = 9.208 (2), c = 49.284 (9), P4(1)2(1)2, Z = 8, R = 0.050)]. The molecular structure of fluorocortisol acetate in the two crystal forms differs primarily in the A ring and acetoxy orientation. The A ring of the steroid in the tetragonal crystal was found to be disordered, and exists in both a normal and inverted conformation. The A ring of the steroid in the monoclinic propanol solvate has the normal (1 alpha, 2 beta half-chain) conformation. The differences in the conformation of the side chain and the A ring appear to reflect the conformational variability in 9 alpha-fluorocortisol acetate.
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Effect of various 6-dehydro-corticosteroids, 9, 11-dehydro-DOCA and 9 alpha-fluoro-DOCA on the fluxes of sodium and potassium.
Arch Int Physiol Biochim
April 1989
Institut de Chimie; CHU, Université de Liège.
The introduction of a double bond at carbons 6 and 7 (6-dehydro-derivatives) of deoxycorticosterone acetate (DOCA), cortisol-21-acetate, 9 alpha-fluorocortisol-21-acetate (9 alpha-F-C-ac) and aldosterone-21-acetate substantially reduces affinity for Type II receptors but not for Type I receptors. Such a modification changes the effect of these steroids on urinary excretion of Na+ and K+. 6-Dehydro-derivatives will thus bind preferentially to receptor Type I inducing the retention of sodium and compete with mineralocorticoids for such receptors.
View Article and Find Full Text PDFThis paper reports the crystal structure of the propanol solvate of 9 alpha-fluorocortisol acetate, which crystallizes in the monoclinic space group P21 [a = 7.470 (6), b = 14.78 (1), c = 12.
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View Article and Find Full Text PDFDeoxycorticosterone acetate (DOCA) and 9 alpha-fluorocortisol acetate (9 alpha-F-Cac) can be modified by the introduction of a double bond at carbons 6 and 7 (6-dehydro-derivatives). Such a modification markedly changes the effect of the steroids on urinary excretion of Na+ and K+. Since 6-7 reduction of DOCA and 9 alpha-F-Cac substantially reduces affinity for Type II receptors but not Type I receptors, 6-dehydro-derivatives will thus bind preferentially to receptors influencing the retention of sodium (the "mineralocorticoid" or Type I receptor), and compete with mineralocorticoids for such receptors.
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