11beta-Hydroxyprogesterone - CAS 600-57-7
Category: Inhibitor
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Molecular Formula:
C21H30O3
Molecular Weight:
330.46
COA:
Inquire
Targets:
Others
Description:
11beta-Hydroxyprogesterone is a potent inhibitors of 11β-Hydroxysteroid dehydrogenase and can confer mineralocorticoid activity on corticosterone in the rat in vivo. 11beta-Hydroxyprogesterone also activates human mineralocorticoid receptor in COS-7 cells with anED50of 10 nM.
Brife Description:
A potent inhibitors of11β-Hydroxysteroid dehydrogenase
Synonyms:
(8S,9S,10R,11S,13S,14S,17S)-17-acetyl-11-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one; 11OHP compound; Duralutin; Gesterol; Hy-Gestrone; Hylutin; Hyprogest; Pergestron; pregn-4-ene-11 beta-ol-3,20-dione; Pro-Depo; Prodrox; 11β-Hydroxyprogesterone
Solubility:
10 mM in DMSO
Storage:
Store in a cool and dry place (or refer to the Certificate of Analysis).
MSDS:
Inquire
Boiling Point:
487.4±45.0 ℃ at 760 Torr
Melting Point:
186-188 ℃
Density:
1.15±0.1 g/cm3
InChIKey:
BFZHCUBIASXHPK-ATWVFEABSA-N
InChI:
1S/C21H30O3/c1-12(22)16-6-7-17-15-5-4-13-10-14(23)8-9-20(13,2)19(15)18(24)11-21(16,17)3/h10,15-19,24H,4-9,11H2,1-3H3/t15-,16+,17-,18-,19+,20-,21+/m0/s1
Canonical SMILES:
CC(=O)C1CCC2C1(CC(C3C2CCC4=CC(=O)CCC34C)O)C
1.Systematic investigation of different steroid precursors with respect to their effect on superoxide anion production by human neutrophil granulocytes.
Békési G;Rácz K;Hrabák A;Kakucs R;Várbíró S;Magyar Z;Fehér J;Dinya E;Pázmány T;Paku S;Székács B Horm Metab Res. 2004 Mar;36(3):155-63.
Free radicals are involved in several pathological processes in living organisms, for example in athero- and oncogenesis. Some steroids are known to be effective antioxidants, while others do not play any such role. The aim of our study was to examine the antioxidant capability of different metabolites in the synthesis of steroid hormones. As a model, we chose human neutrophils producing superoxide anion, which is the source of many other radicals. Neutrophils were separated from healthy volunteers. Isolated cells were incubated with varying concentrations of steroid compounds and stimulated with N-formyl-Met-Leu-Phe. Superoxide anion production was determined by photometry. Neutrophils incubated with corticosterone and 18-hydroxy-deoxycorticosterone showed a significant reduction in superoxide production, whereas we found a significant enhancement in the presence of 11beta-hydroxyprogesterone. Furthermore, we observed a non-significant decreasing trend after incubation with cholesterol 3-sulphate and an increasing tendency using 11-hydroxyandrostenedione. We were also able to produce newer morphological and functional evidence of the role of myeloperoxidase enzyme in the steroidal antioxidant effect by electronic microscopy and use of sodium hypochlorite in our incubation model.
2.Metabolic profiling reveals sphingosine-1-phosphate kinase 2 and lyase as key targets of (phyto-) estrogen action in the breast cancer cell line MCF-7 and not in MCF-12A.
Engel N;Lisec J;Piechulla B;Nebe B PLoS One. 2012;7(10):e47833. doi: 10.1371/journal.pone.0047833. Epub 2012 Oct 24.
To search for new targets of anticancer therapies using phytoestrogens we performed comparative metabolic profiling of the breast cancer cell line MCF-7 and the non-tumorigenic breast cell line MCF-12A. Application of gas chromatography-mass spectrometry (GC-MS) revealed significant differences in the metabolic levels after exposure with 17ß-estradiol, genistein or a composition of phytoestrogens within a native root flax extract. We observed the metabolites 3-(4-hydroxyphenyl)-lactic acid, cis-aconitic acid, 11-beta-hydroxy-progesterone, chenodeoxycholic acid and triacontanoic acid with elevated levels due to estrogen action. Particularly highlighted were metabolites of the sphingolipid metabolism. Sphingosine and its dihydro derivate as well as ethanolaminephosphate were significantly altered after exposure with 1 nM 17ß-estradiol in the cell line MCF-7, while MCF-12A was not affected. Treatment with genistein and the flax extract normalized the sphingosine concentrations to the basic levels found in MCF-12A cells. We could further demonstrate that the expression levels of the sphingosine metabolizing enzymes: sphingosine-1-phosphate kinase (Sphk) and lyase (S1P lyase) were significantly influenced by estrogens as well as phytoestrogens.
3.Gonadal and adrenal catheterization during adrenal suppression and gonadal stimulation in a patient with bilateral testicular tumors and congenital adrenal hyperplasia.
Combes-Moukhovsky ME;Kottler ML;Valensi P;Boudou P;Sibony M;Attali JR J Clin Endocrinol Metab. 1994 Nov;79(5):1390-4.
We report the case of a patient with bilateral testicular tumors and congenital adrenal hyperplasia due to 21-hydroxylase deficiency. Catheterization of the left testicular and adrenal veins was performed. The presence of 11 beta-hydroxylated steroids in the spermatic veins confirmed the presence of testicular tumor secondary to adrenal rest cells. After adrenal suppression by dexamethasone combined with gonadal stimulation with hCG, a dramatic decrease in androgens and adrenal steroids was observed in the peripheral blood. Compared to the periphery, 21-deoxycortisol and 11 beta-hydroxy-delta 4-androstenedione levels remained higher than that of 21-deoxycorticosterone in the gonadal vein, but not in the adrenal vein, which seems to indicate that the nature of this ectopic tissue is unusual and that its sensitivity to dexamethasone depends on the adrenocortical zones. No rise in estradiol or testosterone was obtained after hCG stimulation, suggesting that all of the testicular tissue was inactive or destroyed. This finding was confirmed by histological examination.
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CAS 600-57-7 11beta-Hydroxyprogesterone

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