An androgenic steroid
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Parent Compound(s)
304104-Androsten-11β-ol-3,17-dione
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Adrenosterone

Item No. 45853

Product Insert (PDF)
Technical Information
Formal Name
androst-4-ene-3,11,17-trione
CAS Number
382-45-6
Synonyms
  • 11KA4
  • 11-Ketoandrostenedione
  • NSC 12166
  • 11-Oxoandrostenedione
  • Reichstein's Substance G
Molecular Formula
C19H24O3
Formula Weight
300.4
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: Soluble: ≥10 mg/ml
SMILES
C[C@@]12[C@]3([H])[C@](CCC1=CC(CC2)=O)([H])[C@@]4([H])[C@](CC3=O)(C(CC4)=O)C
InChi Code
InChI=1S/C19H24O3/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/h9,13-14,17H,3-8,10H2,1-2H3/t13-,14-,17+,18-,19-/m0/s1
InChi Key
RZRPTBIGEANTGU-IRIMSJTPSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Adrenosterone is an androgenic steroid and a metabolite of DHEA (Item No. 10007534) that is produced in the adrenal glands in mammals and teleost fish.1,2 It is formed from DHEA via the sequential actions of 3β-HSD2, CYP11B1, and 11β-HSD2, with androstenedione and 4-androsten-11β-ol-3,17-dione (11OHA3; Item No. 30410) as intermediates.1,3 Adrenosterone induces androgen receptor transactivation in MDA-kb2 cells expressing the human receptor (EC50 = 469 nM).2 Levels of adrenosterone are increased in LNCaP prostate cancer cells and in the serum of patients with classic 21-hydroxylase deficiency (21OHD), a type of congenital adrenal hyperplasia (CAH) characterized by cortisol deficiency and hypotension.3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Pretorius, E., Arlt, W., and Storbeck, K.-H. A new dawn for androgens: Novel lessons from 11-oxygenated C19 steroids. Mol. Cell. Endocrinol. 441, 76-85 (2017).

    2. Rege, J., Nakamura, Y., Satoh, F., et al. Liquid chromatography-tandem mass spectrometry analysis of human adrenal vein 19-carbon steroids before and after ACTH stimulation. J. Clin. Endocrinol. Metab. 98(3), 1182-1188 (2013).

    3. Swart, A.C., Schloms, L., Storbeck, K.-H., et al. 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, 132-142 (2013).

    4. Turcu, A.F., Nanba, A.T., Chomic, R., et al. Adrenal-derived 11-oxygenated 19-carbon steroids are the dominant androgens in classic 21-hydroxylase deficiency. Eur. J. Endocrinol. 174(5), 601-609 (2016).