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Statements

Subject Item
n2:DB01708
rdf:type
n3:Drug
n3:description
Dehydroepiandrosterone (DHEA) is a major C19 steroid produced by the adrenal cortex. It is also produced in small quantities in the testis and the ovary. Dehydroepiandrosterone (DHEA) can be converted to testosterone; androstenedione; estradiol; and estrone. Most of DHEA is sulfated (dehydroepiandrosterone sulfate) before secretion. In the United States, DHEA or DHEAS have been advertised with claims that they may be beneficial for a wide variety of ailments. DHEA and DHEAS are readily available in the United States, where they are marketed as over-the-counter dietary supplements. In Canada, a prescription is required to buy DHEA.
n3:generalReferences
# "The NIH National Library of Medicine":http://www.nlm.nih.gov/medlineplus/druginfo/natural/patient-dhea.html # Baker WL, Karan S, Kenny AM: Effect of dehydroepiandrosterone on muscle strength and physical function in older adults: a systematic review. J Am Geriatr Soc. 2011 Jun;59(6):997-1002. doi: 10.1111/j.1532-5415.2011.03410.x. Epub 2011 Jun 7. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/21649617 # Alkatib AA, Cosma M, Elamin MB, Erickson D, Swiglo BA, Erwin PJ, Montori VM: A systematic review and meta-analysis of randomized placebo-controlled trials of DHEA treatment effects on quality of life in women with adrenal insufficiency. J Clin Endocrinol Metab. 2009 Oct;94(10):3676-81. Epub 2009 Sep 22. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/19773400 # Arlt W: Dehydroepiandrosterone and ageing. Best Pract Res Clin Endocrinol Metab. 2004 Sep;18(3):363-80. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/15261843 # Wallace MB, Lim J, Cutler A, Bucci L: Effects of dehydroepiandrosterone vs androstenedione supplementation in men. Med Sci Sports Exerc. 1999 Dec;31(12):1788-92. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/10613429 # Grimley Evans J, Malouf R, Huppert F, van Niekerk JK: Dehydroepiandrosterone (DHEA) supplementation for cognitive function in healthy elderly people. Cochrane Database Syst Rev. 2006 Oct 18;(4):CD006221. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/17054283 # Fuller SJ, Tan RS, Martins RN: Androgens in the etiology of Alzheimer's disease in aging men and possible therapeutic interventions. J Alzheimers Dis. 2007 Sep;12(2):129-42. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/17917157 # Casson PR, et al. Dehydroepiandrosterone supplementation augments ovarian stimulation in poor responders: a case series. Hum Reprod, 2000;15:2129-2132. # Thijs L, Fagard R, Forette F, Nawrot T, Staessen JA: Are low dehydroepiandrosterone sulphate levels predictive for cardiovascular diseases? A review of prospective and retrospective studies. Acta Cardiol. 2003 Oct;58(5):403-10. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/14609305 # Barrett-Connor E, Khaw KT, Yen SS: A prospective study of dehydroepiandrosterone sulfate, mortality, and cardiovascular disease. N Engl J Med. 1986 Dec 11;315(24):1519-24. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/2946952 # Arnlov J, Pencina MJ, Amin S, Nam BH, Benjamin EJ, Murabito JM, Wang TJ, Knapp PE, D'Agostino RB Sr, Bhasin S, Vasan RS: Endogenous sex hormones and cardiovascular disease incidence in men. Ann Intern Med. 2006 Aug 1;145(3):176-84. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/16880459 # Crosbie D, Black C, McIntyre L, Royle PL, Thomas S: Dehydroepiandrosterone for systemic lupus erythematosus. Cochrane Database Syst Rev. 2007 Oct 17;(4):CD005114. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/17943841 # Chang DM, Lan JL, Lin HY, Luo SF. Dehydroepiandrosterone treatment of women with mild-to-moderate systemic lupus erythematosus: a multicenter randomized, double-blind, placebo-controlled trial. Arthritis Rheum. 2002 Nov;46(11):2924-7. # Mattison JA, Lane MA, Roth GS, Ingram DK: Calorie restriction in rhesus monkeys. Exp Gerontol. 2003 Jan-Feb;38(1-2):35-46. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/12543259 # Roberts E: The importance of being dehydroepiandrosterone sulfate (in the blood of primates): a longer and healthier life? Biochem Pharmacol. 1999 Feb 15;57(4):329-46. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/9933021 # Leblanc M, Labrie C, Belanger A, Candas B, Labrie F: Bioavailability and pharmacokinetics of dehydroepiandrosterone in the cynomolgus monkey. J Clin Endocrinol Metab. 2003 Sep;88(9):4293-302. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/12970301
n3:group
nutraceutical
n3:halfLife
12 hours
n3:indication
DHEA is taken as a supplement for a variety of unsubstantiated indications. The following indications have shown promise and are backed up by some scientific evidence: schizophrenia (DHEA may be more effective in women than men); improving the appearance of older people’s skin (taking DHEA by mouth seems to increase skin thickness and moisture, and decrease facial “age spots” in elderly men and women); improving ability to achieve an erection in men with sexual dysfunction. Additionally, DHEA has shown promise in improving symptoms of lupus (SLE). Taking DHEA by mouth along with conventional treatment may help reduce the number of times symptoms flare up and may allow a reduction in the dose of prescription drugs needed. DHEA may also help SLE symptoms such as muscle ache and mouth ulcers. DHEA also seems to strengthen bones in SLE patients being treated with high-dose steroids (corticosteroids). DHEA also shows promise in the treatment of osteoporosis. Taking DHEA by mouth daily seems to improve bone mineral density (BMD) in older women and men with osteoporosis or osteopenia (pre-osteoporosis). DHEA may also increase BMD in young women with the eating disorder called anorexia nervosa. DHEA is often prescribed in India for the induction of ovulation to improve chances of pregnancy.
owl:sameAs
n9:DB01708 n13:DB01708
dcterms:title
Dehydroepiandrosterone
adms:identifier
n6:PA451993 n7:Dehydroepiandrosterone n14:46508824 n15:AND n16:5881 n17:2370 n18:C01227 n19:DB01708 n20:2370 n21:28689 n22:5670
n3:mechanismOfAction
DHEA can be understood as a prohormone for the sex steroids. DHEAS may be viewed as buffer and reservoir. As most DHEA is produced by the zona reticularis of the adrenal cortex, it is argued that there is a role in the immune and stress response. As almost all DHEA is derived from the adrenal glands, blood measurements of DHEAS/DHEA are useful to detect excess adrenal activity as seen in adrenal cancer or hyperplasia, including certain forms of congenital adrenal hyperplasia. Women with polycystic ovary syndrome tend to have elevated levels of DHEAS.
n3:synonym
5-DHEA 3-beta-Hydroxy-5-androsten-17-one DHA DHEA Prasterone 5-Dehydroepiandrosterone
n3:toxicity
Acute oral toxicity (LD50): >10000 mg/kg [Rat]. Lowest Published Toxic Dose (TDL) [Man] - Route: Oral; Dose: 10 mg/kg/2W intermittent.
n3:synthesisReference
Isao Sugimoto, Yoko Sawase, "Stable preparation of water-soluble salts of dehydroepiandrosterone sulfate for parenteral administration." U.S. Patent US4061744, issued January, 1977.
n10:hasConcept
n11:M0005765
n3:IUPAC-Name
n4:271B3EE5-363D-11E5-9242-09173F13E4C5
n3:InChI
n4:271B3EEB-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n4:271B3EEA-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n4:271B3EE7-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n4:271B3EE8-363D-11E5-9242-09173F13E4C5
n3:SMILES
n4:271B3EE9-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n4:271B3EFB-363D-11E5-9242-09173F13E4C5 n4:271B3EE3-363D-11E5-9242-09173F13E4C5
n3:logP
n4:271B3EE4-363D-11E5-9242-09173F13E4C5 n4:271B3EFD-363D-11E5-9242-09173F13E4C5 n4:271B3EE1-363D-11E5-9242-09173F13E4C5
n3:logS
n4:271B3EE2-363D-11E5-9242-09173F13E4C5
n23:hasATCCode
n24:A14AA07
n3:H-Bond-Acceptor-Count
n4:271B3EF1-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n4:271B3EF2-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n4:271B3EEC-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n4:271B3EED-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n4:271B3EEF-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n4:271B3EEE-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n4:271B3EF0-363D-11E5-9242-09173F13E4C5
n3:absorption
Following a 50-mg DHEA PO dose in cynomolgus monkeys, systemic availability was only 3.1 +/- 0.4%. [PMID: 12970301]
n3:affectedOrganism
Humans and other mammals
n3:casRegistryNumber
53-43-0
n3:category
n3:Bioavailability
n4:271B3EF7-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n4:271B3EF9-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n4:271B3EFA-363D-11E5-9242-09173F13E4C5
n3:Melting-Point
n4:271B3EFC-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n4:271B3EF6-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n4:271B3EF5-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n4:271B3EF8-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n4:271B3EE6-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n4:271B3EF3-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n4:271B3EF4-363D-11E5-9242-09173F13E4C5