CAS 382-44-5|11-Beta-hydroxyandrostenedione
| Common Name | 11-Beta-hydroxyandrostenedione | ||
|---|---|---|---|
| CAS Number | 382-44-5 | Molecular Weight | 302.408 |
| Density | 1.2±0.1 g/cm3 | Boiling Point | 475.3±45.0 °C at 760 mmHg |
| Molecular Formula | C19H26O3 | Melting Point | 197-199℃ |
| MSDS | ChineseUSA | Flash Point | 255.4±25.2 °C |
Names
| Name | 11β-hydroxyandrost-4-ene-3,17-dione |
|---|---|
| Synonym | More Synonyms |
11-Beta-hydroxyandrostenedione BiologicalActivity
| Description | 11-Beta-hydroxyandrostenedione (4-Androsten-11β-ol-3,17-dione) is a steroid mainly found in the the adrenal origin (11β-hydroxylase is present in adrenal tissue, but absent in ovarian tissue). 11-Beta-hydroxyandrostenedione is a 11β-hydroxysteroid dehydrogenase (11βHSD) isozymes inhibitor. As 4-androstenedione increases, measuring plasma 11-Beta-hydroxyandrostenedione can distinguish the adrenal or ovarian origin of hyperandrogenism[1][2]. |
|---|---|
| Related Catalog | Research Areas >>Endocrinology |
| Target | Human Endogenous Metabolite |
| In Vitro | In order to establish that this conversion is catalysed by the lyase activity of CYP17A1, 21-deoxycortisol (21dF) and 21-deoxycortisone (21dE) is assayed within the LNCaP cell line. Upon the transfection of CYP17A1, 11-Beta-hydroxyandrostenedione (11OHA4)-pathway metabolites increase, 21dF and 21dE are in fact metabolised to 11-Beta-hydroxyandrostenedione and 11-ketoprogesterone (11KP4) by CYP17A1, respectively[2]. |
| In Vivo | The plasma concentration of 11-Beta-hydroxyandrostenedione (11beta-hydroxy-4-androstene-3,17-dione) is very high in 21-hydroxylase deficiency, Cushing's syndrome, and hyperandrogenism of adrenal origin, and very low in congenital 11-hydroxylase deficiency and adrenal insufficiency. Thus, when plasma 4-androstenedione is elevated, it is useful to measure the plasma 11-Beta-hydroxyandrostenedione level in order to determine the adrenal or ovarian origin of the hyperandrogenism[1]. |
| References | [1]. Ibrahim F, et al. Plasma 11beta-hydroxy-4-androstene-3,17-dione: comparison of a time-resolved fluoroimmunoassay using a biotinylated tracer with a radioimmunoassay using a tritiated tracer. J Steroid Biochem Mol Biol. 2003 Apr;84(5):563-8. [2]. Rachelle Gent, et al. 11α-Hydroxyprogesterone, a potent 11β-hydroxysteroid dehydrogenase inhibitor, is metabolised by steroid-5α-reductase and cytochrome P450 17αhydroxylase/17,20-lyase to produce C11α-derivatives of 21-deoxycortisol |
Chemical & Physical Properties
| Density | 1.2±0.1 g/cm3 |
|---|---|
| Boiling Point | 475.3±45.0 °C at 760 mmHg |
| Melting Point | 197-199℃ |
| Molecular Formula | C19H26O3 |
| Molecular Weight | 302.408 |
| Flash Point | 255.4±25.2 °C |
| Exact Mass | 302.188202 |
| PSA | 54.37000 |
| LogP | 1.27 |
| Vapour Pressure | 0.0±2.7 mmHg at 25°C |
| Index of Refraction | 1.569 |
| InChIKey | WSCUHXPGYUMQEX-KCZNZURUSA-N |
| SMILES | CC12CC(O)C3C(CCC4=CC(=O)CCC43C)C1CCC2=O |
Safety Information
| Personal Protective Equipment | Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter |
|---|---|
| RIDADR | NONH for all modes of transport |
| WGK Germany | 3.0 |
Articles27
More Articles| 11β-Hydroxyandrostenedione, the product of androstenedione metabolism in the adrenal, is metabolized in LNCaP cells by 5α-reductase yielding 11β-hydroxy-5α-androstanedione J. Steroid Biochem. Mol. Biol. 138 , 132-42, (2013) • Etomidate inhibited DOC, deoxycortisol, A4 and T conversion in H295R cells. • CYP11B1 11β-hydroxylates A4 and T; CYP11B2 11β-hydroxylates T. • 11βHSD1 converts 11KA4 and 11KT; 11βHSD2 converts 11OHA... | |
| Oxygen availability as a regulatory factor of androgen synthesis by adrenocortical cells. Endocrinology 132(1) , 255-60, (1993) Molecular oxygen is an obligatory substrate of all cytochrome P-450 (cyt P-450) hydroxylases involved in the steroid biosynthetic pathways. However, oxygen-derived free radicals are highly destructive... | |
| 11beta-hydroxyandrostenedione and delta5-androstenediol as markers of adrenal androgen production in patients with 21-hydroxylase-deficient nonclassic adrenal hyperplasia. Fertil. Steril. 72(6) , 996-1000, (1999) To determine the sensitivity of 11beta-hydroxyandrostenedione (11-OHA4) and delta5-androstenediol (ADIOL) as markers of excessive adrenal androgen production.Prospective study.Academic medical centers... |
Synonyms
| (8S,9S,10R,11S,13S,14S)-11-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dione |
| Androst-4-ene-3,17-dione, 11β-hydroxy- |
| U 2826 |
| Androst-4-ene-3,17-dione, 11-hydroxy-, (11β)- |
| 11β-hydroxyandrost-4-ene-3,17-dione |
| (11β)-11-Hydroxyandrost-4-ene-3,17-dione |
| 4-Androsten-11beta-ol-3,17-dione |
| 11beta-Hydroxyandrostenedione |
| 11β-Hydroxy-4-androsten-3,17-dione |
| 11beta-Hydroxyandrost-4-ene-3,17-dione |
| Androst-4-ene-3,17-dione-11beta-ol |
| 11b-Hydroxyandrost-4-ene-3,17-dione |
