4296 Dehydroepiandrosterone sulfate Dehydroepiandrosterone sulfate or DHEAS is the sulfated form of dehydroepiandrosterone (DHEA). This sulfation is reversibly catalyzed by sulfotransferase 2A1 (SULT2A1) primarily in the adrenals, the liver, and small intestine. In the blood, most DHEA is found as DHEAS with levels that are about 300 times higher than those of free DHEA. Orally-ingested DHEA is converted to its sulfate when passing through intestines and liver. Whereas DHEA levels naturally reach their peak in the early morning hours, DHEAS levels show no diurnal variation. From a practical point of view, measurement of DHEAS is preferable to DHEA, as levels are more stable. DHEA (from which DHEAS comes from) is a natural steroid prohormone produced from cholesterol by the adrenal glands, the gonads, adipose tissue, brain and in the skin (by an autocrine mechanism). DHEA is the precursor of androstenedione, which can undergo further conversion to produce the androgen testosterone and the estrogens estrone and estradiol. DHEA is also a potent sigma-1 agonist. DHEAS can serve as a precursor for testosterone; androstenedione; estradiol; and estrone. Serum dehydroepiandrosterone sulfate is a classic marker for adrenarche and, subsequently, for the individual hormonal milieu Dehydroepiandrosterone sulfate is an endogenously produced sex steroid that has been hypothesized to have anti aging effects It also has been inversely associated with development of atherosclerosis (A3325, A3326, A3327). DHEA-S is the principal adrenal androgen and is secreted together with cortisol under the control of ACTH and prolactin. DHEA-S is elevated with hyperprolactinemia. 651-48-9 12594 C19H28O5S White powder. Endogenous, ingestion Although it predominantly functions as an endogenous precursor to more potent androgens such as testosterone and dihydroxytestosterone, DHEA (which is produced from DHEAS) has been found to possess some degree of androgenic activity in its own right, acting as a low affinity (Ki = 1 μM), weak partial agonist of the androgen receptor. DHEA has also been found to bind to and activate the ERα and ERβ estrogen receptors with Ki values of 1.1 μM and 0.5 μM, respectively. When taken in sufficient quantities DHEAS can cause masculinizing effects. DHEAS is considered an androgenic steroid precursor because testosterone (its product) is an androgen or male hormone. In males and females, conversion of DHEAS to testosterone requires the enzyme 17β-hydroxysteroid dehydrogenase. Testosterone plays a key role in the development of male reproductive tissues such as the testis and prostate as well as promoting secondary sexual characteristics such as increased muscle, bone mass, and the growth of body hair. High levels of testosterone can lead to masculinization in females or premature puberty in young boys. Chronically high levels in adults increase the incidence of heart attack, stroke and blood clots by lowering the level of HDL (good cholesterol). The development of breast tissue in males, a condition called gynecomastia (which is usually caused by high levels of circulating estradiol), arises because of increased conversion of testosterone to estradiol by the enzyme aromatase. Reduced sexual function and temporary infertility can also occur in males. Dehydroepiandrosterone sulfate (DHEAS) is the sulfate ester of DHEA. This conversion is reversibly catalyzed by sulfotransferase (SULT2A1) primarily in the adrenals, the liver, and small intestine. DHEA sulfate can also be back-converted to DHEA through the action of steroid sulfatase. In the blood, most DHEA is found as DHEAS with levels that are about 300 times higher than those of free DHEA. Orally ingested DHEA is converted to its sulfate when passing through intestines and liver. DHEAS levels show no diurnal variation. In males and females, conversion of DHEAS to DHEA and then to testosterone requires the enzyme 17β-hydroxysteroid dehydrogenase. No indication of carcinogenicity to humans (not listed by IARC). Investigated for use/treatment in asthma and burns and burn infections. Dehydroepiandrosterone sulfate levels above 1890 micromol/L or 700-800 µg/dL are highly suggestive of adrenal dysfunction. Some researchers believe DHEAS supplements might actually raise the risk of breast cancer, prostate cancer, heart disease, diabetes and stroke. DHEAS may stimulate tumor growth in types of cancer that are sensitive to hormones, such as some types of breast, uterine, and prostate cancer. DHEAS may increase prostate swelling in men with benign prostatic hyperplasia (BPH), an enlarged prostate gland. High doses of DHEAS may cause aggressiveness, irritability, trouble sleeping, and the growth of body or facial hair on women. It also may stop menstruation and lower the levels of HDL ('good' cholesterol), which could raise the risk of heart disease. Other reported side effects include acne, heart rhythm problems, liver problems, hair loss (from the scalp), and oily skin. In women, DHEA may cause decreased breast size, a deep voice, increased genital size, irregular periods, oily skin, and unnatural hair growth. In men, DHEAS may cause aggression, breast tenderness or enlargement, decreased testes size, and urinary urgency. DHEAS may interfere with the way the body processes certain agents using the liver's cytochrome P450 enzyme system. Chronically high levels of Dehydroepiandrosterone sulfate are associated with male pseudohermaphrodism with gynecomastia. In women, DHEAS may cause decreased breast size, a deep voice, increased genital size, irregular periods, oily skin, and unnatural hair growth. In men, DHEAS may cause aggression, breast tenderness or enlargement, decreased testes size, and urinary urgency. 2014-08-29T06:00:38Z 2026-05-14T18:16:20Z Dehydroepiandrosterone C04555 16814 DEHYDRO-EPIANDROSTERONE-SULFATE DB05804 true [H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@H](CC[C@]12C)OS(O)(=O)=O C19H28O5S InChI=1S/C19H28O5S/c1-18-9-7-13(24-25(21,22)23)11-12(18)3-4-14-15-5-6-17(20)19(15,2)10-8-16(14)18/h3,13-16H,4-11H2,1-2H3,(H,21,22,23)/t13-,14-,15-,16-,18-,19-/m0/s1 CZWCKYRVOZZJNM-USOAJAOKSA-N 368.488 368.165744696 Endogenous Solid HMDB01032 CHEMBL259898 12074 CHEM003202 DTXSID8040228 [(3aS,3bR,7S,9aR,9bS,11aS)-9a,11a-dimethyl-1-oxo-1H,2H,3H,3aH,3bH,4H,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid 80.67 94.6507 39.8474725985752 2 4 1 -1.3632754765266997 -7.4756492107864165 -1 4 0.49 -4.66 8.06e-03 g/l