11-Beta-hydroxyandrostenedione

Modify Date: 2024-01-04 18:04:40

11-Beta-hydroxyandrostenedione Structure
11-Beta-hydroxyandrostenedione structure
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 Chinese USA Flash Point 255.4±25.2 °C

 Use of 11-Beta-hydroxyandrostenedione


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].

 Names

Name 11β-hydroxyandrost-4-ene-3,17-dione
Synonym More Synonyms

 11-Beta-hydroxyandrostenedione Biological Activity

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
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

 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

 Synthetic Route

 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