Dehydro-epiandrosterone

Kullak-Ublick, G. A., et al. Dehydro-epiandrosterone sulfate (DHEAS) identification of a carrier protein in human liver and brain. FEBS Lett. 1998, 424, 173-176. 

The biologically inactive estrone sulfate (EIS) and dehydro-epiandrosterone-sulfate (DHEAS) are the most abundant circulating estrogenic precursors in the plasma of post-menopausal women [103]. Desulfation of inactive steroid-3-0-sulfates by estrone-sulfatase (STS) plays a key role in the regulation of levels of receptor-active estrogenic steroids (estradiol and androstenediol) in breast cancer cells (Fig. 9). There is strong evidence suggesting that estrone sulfatase (STS) and DHEA-sulfatase are the same enzyme [103]. 

Serum sex hormones effect. DION (300 mg androstenedione, 150 mg dehydro-epiandrosterone, 540 mg saw palmetto, 300 mg indole-3-carbinol, 625 mg chrysin, 750 mg Tribulus terrestris), administered daily to healthy 30- to 59-year-old men for 28 days, produced no change in serum concentrations of total T and PSA. DION increased the concentrations of serum androstenedione (342%), free T (38%), DHT (71%), and estradiol (103%). Serum high-density lipoprotein (HDL) cholesterol concentrations were reduced by 5 mg/dL in DION (p < 0.05). Increases in serum free T (r = 0.01), androstenedione (r = 0.01), DHT (r = 0.03), or estradiol (r = 0.07) concentrations in DION were not related to age. The ingestion of androstenedione combined with herbal products increased serum-free T concentrations in older men, but herbal products did not prevent the conversion of... 

The solution was dried over sodium sulfate and exaporated. 13.6 g of crude dehydro-epiandrosterone-3-oenanthate were obtained, melting point 70°-72°C (recrystallisation from methanol). 

Orentreich N, Brind JL, Rizer RL, Vogelman JH. Age changes and sex differences in serum dehydro epiandrosterone sulfate levels throughout adulthood. J Clin Endocrinol Metab 1984 59 551-5. 

Figure 54-1 Schematic representation of steroid and protein hormone production by the placenta. DHEA-S, Dehydro-epiandrosterone sulfate CG, chorionic gonadotropin PL, placental lactogen ACTH, adrenocorticotropic hormone TRH, thyroid-stimulating hormone CT, chorionic thyrotropin GnRH, gonadotropin-releasing hormone CRH, corticotropin-releasing hormone PAPP-A, pregnancy associated plasma protein-A.

M9. Michie, E. A., Oestrogen levels in urine and amniotic fluid in pregnancy with live anencephalic foetus and the effect of intrar-amniotic injection of sodium dehydro-epiandrosterone sulphate on these levels. Acta Endocrinol. 61, 535-542 (1966). 

Kitada, M., T. Kamataki, K. Itahashi, T. Rikihisa, and Y. Kanakubo (1987). P-450 HFLa, a form of cytochrome P-450 purified from human fetal livers, is the 16 alpha-hydroxylase of dehydro-epiandrosterone 3-sulfate. J. Biol. Chem. 262, 13534-13537. 

Abiraterone acetate 117 is an androgen biosynthesis inhibitor, which was developed by the Institute of Cancer Research in the UK and further developed by Janssen for the oral treatment of patients with metastatic castration-resistant prostate cancer [75]. Its synthesis is relatively easy through a Suzuki coupling between the 17-enol triflate derived from the 3-acetate of dehydro-epiandrosterone (115) and 3-pyridyl-diethylborane (116) (Scheme 27) [76]. The reaction is catalysed by PdCl2(PPh3)2 and proceeds in good yield (84%). A similar Suzuki-based route in which the ketone starting material was converted into an alkenyliodide has also been published [77]. 

These are a group of C-19 steroids which influence the male secondary sex characteristics. They are made by the testes, adrenals and to a lesser extent by the ovaries. The testes secrete testosterone while the main adrenal androgens are dehydro-epiandrosterone and androstenedione. Urinary 17-oxosteroid estimations give an indication of androgen production. 

As indicated previously (Section 111, F, 1 and 2), the two quantitatively most important steroids circulating in the fetal compartment are dehydro-epiandrosterone sulfate and 16a-hydroxydehydroepiandrosteronc sulfate. The concentration of these two steroids is higher in the umbilical artery than in the umbilical vein, indicating their production in the fetal compartment and their secretion to the placenta, in placental tissue, the major part of these steroid conjugatiis is hydrolyzed and aromatized and the respective estrogens (estrone, 17d-est.radiol, and estriol) are largely transferred to the mother while a small part returns to the fetus. 

SYNS (3-p,5-a)-3-(ACETYLOXY)ANDROSTAN-17-ONE ANDROSTAN-17-ONE, 3-(ACETYLOXY)-, (3-P,5-a)- DEHYDROEPIANDROSTERONE ACETATE EPIANDROSTERONE, DEHYDRO-, ACETATE ANDROSTEN-17-ONE, 3-p-HYDROXY-, ACETATE... 

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