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A3009

Sigma-Aldrich

4-Androsten-11β-ol-3,17-dione

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Synonym(s):
11β-Hydroxy-4-androstene-3,17-dione
Empirical Formula (Hill Notation):
C19H26O3
CAS Number:
Molecular Weight:
302.41
MDL number:
PubChem Substance ID:
NACRES:
NA.77

assay

≥98.00% (TLC)

Quality Level

form

powder

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada

solubility

chloroform: 49-51 mg/mL, clear, colorless to faintly yellow

shipped in

ambient

Storage temp.

room temp

SMILES string

[H][C@@]12CCC3=CC(=O)CC[C@]3(C)[C@@]1([H])[C@@H](O)C[C@]4(C)C(=O)CC[C@@]24[H]

InChI

1S/C19H26O3/c1-18-8-7-12(20)9-11(18)3-4-13-14-5-6-16(22)19(14,2)10-15(21)17(13)18/h9,13-15,17,21H,3-8,10H2,1-2H3/t13-,14-,15-,17+,18-,19-/m0/s1

Inchi Key

WSCUHXPGYUMQEX-KCZNZURUSA-N

Biochem/physiol Actions

11β-Hydroxy-4-androstene-3,17-dione is a naturally occurring steroid that is primarily, if not strictly, produced in adrenal tissue. In diseases such as Cushing′s syndrome, adrenal-originated hyperandrogenism, and congenital adrenal hyperplasia, plasma 11β levels are very high. Plasma 11β concentration is very low in congenital 11-hydroxylase deficiency and adrenal insufficiency.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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M Bicíková et al.
Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme, 29(9), 465-468 (1997-11-25)
With regard to previous finding of an inhibitory activity of furosemide on 11 beta-hydroxysteroid dehydrogenase, 16 other commonly used diuretics have been tested as to their ability to inhibit rat renal, and in four instances also testicular 11 beta-hydroxysteroid dehydrogenase
Fidaa Ibrahim et al.
The Journal of steroid biochemistry and molecular biology, 84(5), 563-568 (2003-05-28)
The plasma concentration of 11beta-hydroxy-4-androstene-3,17-dione (11beta) 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
P Liakos et al.
The Journal of endocrinology, 176(1), 69-82 (2003-01-15)
Transforming growth factor beta1 (TGFbeta1) has been shown to exert strong inhibitory effects on adrenocortical cell steroidogenesis. However, the molecular targets of TGFbeta1 in adrenocortical cells appear to differ between species. Here, we report the first characterization of the regulatory
R Huerta et al.
Fertility and sterility, 72(6), 996-1000 (1999-12-11)
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. Thirteen women with untreated 21-hydroxylase-deficient nonclassic adrenal hyperplasia (NCAH) and 18 healthy, eumenorrheic, nonhirsute controls matched for age
F Z Stanczyk et al.
American journal of obstetrics and gynecology, 165(6 Pt 1), 1837-1842 (1991-12-01)
To determine whether the adrenal androgen 11 beta-hydroxyandrostenedione is a more sensitive and specific marker than dehydroepiandrosterone sulfate, we compared these serum androgens in 81 women with anovulatory hyperandrogenism before treatment, after corticotropin and corticotropin-releasing-factor stimulation, and after short- and

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