16-Hydroxydehydroepiandrosterone sulfate
16-Hydroxydehydroepiandrosterone sulfate (16-OH-DHEAS) is a steroid metabolite of dehydroepiandrosterone (DHEA) that is produced in the adrenal gland. It is a sulfate conjugate of 16α-hydroxy-DHEA, which is formed by the action of hydroxysteroid sulfotransferase enzymes in the liver and adrenal cortex.
Structure and Properties[edit | edit source]
16-OH-DHEAS is a hydroxylated and sulfated derivative of DHEA, a precursor to sex steroids. It has a molecular weight of 402.49 g/mol and a chemical formula of C19H28O8S. The hydroxylation at the 16α position and the addition of a sulfate group increase the water solubility of the molecule, facilitating its excretion in the urine.
Biosynthesis and Metabolism[edit | edit source]
The biosynthesis of 16-OH-DHEAS begins with the conversion of cholesterol to pregnenolone in the mitochondria of adrenal cells. Pregnenolone is then converted to DHEA by the sequential action of 17α-hydroxylase and 17,20-lyase. The 16α-hydroxylation of DHEA is catalyzed by cytochrome P450 enzymes, and the resulting 16α-hydroxy-DHEA is sulfated by hydroxysteroid sulfotransferases to form 16-OH-DHEAS.
16-OH-DHEAS is metabolized primarily in the liver, where it can be desulfated and further metabolized to other steroid hormones, or excreted in the urine.
Biological Activity[edit | edit source]
16-OH-DHEAS has been found to have weak androgenic and estrogenic activity, similar to other DHEA metabolites. However, its physiological role is not fully understood. It has been suggested that 16-OH-DHEAS may serve as a reservoir for the production of other active steroids, or that it may have unique biological effects of its own.
Clinical Significance[edit | edit source]
Elevated levels of 16-OH-DHEAS in the blood or urine can be indicative of an adrenal disorder, such as adrenal hyperplasia or an adrenal tumor. Measurement of 16-OH-DHEAS levels can therefore be useful in the diagnosis and monitoring of these conditions.
Search WikiMD
Ad.Tired of being Overweight? Try W8MD's physician weight loss program.
Semaglutide (Ozempic / Wegovy and Tirzepatide (Mounjaro / Zepbound) available.
Advertise on WikiMD
WikiMD's Wellness Encyclopedia |
Let Food Be Thy Medicine Medicine Thy Food - Hippocrates |
Translate this page: - East Asian
中文,
日本,
한국어,
South Asian
हिन्दी,
தமிழ்,
తెలుగు,
Urdu,
ಕನ್ನಡ,
Southeast Asian
Indonesian,
Vietnamese,
Thai,
မြန်မာဘာသာ,
বাংলা
European
español,
Deutsch,
français,
Greek,
português do Brasil,
polski,
română,
русский,
Nederlands,
norsk,
svenska,
suomi,
Italian
Middle Eastern & African
عربى,
Turkish,
Persian,
Hebrew,
Afrikaans,
isiZulu,
Kiswahili,
Other
Bulgarian,
Hungarian,
Czech,
Swedish,
മലയാളം,
मराठी,
ਪੰਜਾਬੀ,
ગુજરાતી,
Portuguese,
Ukrainian
Medical Disclaimer: WikiMD is not a substitute for professional medical advice. The information on WikiMD is provided as an information resource only, may be incorrect, outdated or misleading, and is not to be used or relied on for any diagnostic or treatment purposes. Please consult your health care provider before making any healthcare decisions or for guidance about a specific medical condition. WikiMD expressly disclaims responsibility, and shall have no liability, for any damages, loss, injury, or liability whatsoever suffered as a result of your reliance on the information contained in this site. By visiting this site you agree to the foregoing terms and conditions, which may from time to time be changed or supplemented by WikiMD. If you do not agree to the foregoing terms and conditions, you should not enter or use this site. See full disclaimer.
Credits:Most images are courtesy of Wikimedia commons, and templates Wikipedia, licensed under CC BY SA or similar.
Contributors: Prab R. Tumpati, MD