11-Beta-hydroxyandrostenedione

Names

[ CAS No. ]:
382-44-5

[ Name ]:
11-Beta-hydroxyandrostenedione

[Synonym ]:
(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

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]:

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

MSDS

Click to get detail MSDS

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

Click to get detail synthetic route

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...