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D4000 Sigma

trans-Dehydroandrosterone

≥99%

Synonym: 3β-Hydroxy-5-androsten-17-one, 5-Androsten-3β-ol-17-one, DHEA, Dehydroepiandrosterone, Dehydroisoandrosterone, Prasterone

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Properties

Related Categories Androgen, Cancer Research, Cell Biology, Cell Signaling and Neuroscience, Cytokines, Growth Factors and Hormones,
assay   ≥99%
drug control   Home Office Schedule 4.2regulated under CDSA - not available from Sigma-Aldrich Canada
mp   149-151 °C(lit.)
Gene Information   human ... GABRA1(2554), GABRA2(2555), GABRA3(2556), GABRA4(2557), GABRA5(2558), GABRA6(2559), GABRB1(2560), GABRB2(2561), GABRB3(2562), SERPINA6(866)
rat ... Ar(24208)

Description

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10, 25, 100, 250 g in poly bottle

Biochem/physiol Actions

Dehydroandrosterone (DHEA) is a negative modulator of GABAA receptors. It is a steroid secreted by the adrenal gland with both estrogenic and androgenic properties. DHEAs conversion to 5-androstenediol, a potent estrogen, enhances the growth and survival of estrogen-sensitive breast tumors.

Negative modulator of GABAA receptors. Steroid secreted by the adrenal gland with both estrogenic and androgenic properties. Its conversion to 5-androstenediol, a potent estrogen, enhances the growth and survival of estrogen-sensitive breast tumors. At high but physiologically valid concentrations, DHEA inhibits proliferation of chromaffin progenitor cells and induces dopaminergic differentiation.

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GHS07  GHS07
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WGK Germany 
2
RTECS 
BV8396000

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Peer-Reviewed Papers

References

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Physiological importance of dehydroepiandrosterone. Ebeling, P., and Koivisto, V.A. Lancet 343, 1479-1481, (1994)

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Role of steroid sulfatase in local formation of estrogen in post-menopausal breast cancer patients. Nakata, T., et al. J. Steroid Biochem. Mol. Biol. 86, 455-460, (2003)

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Neurosteroids as modulators of neurogenesis and neuronal survival. Charalampopoulos I, Remboutsika E, et. al. Trends Endocrinol. Metab. 19, 300-307, (2008)

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Effects of dehydroepiandrosterone on proliferation and differentiation of chromaffin progenitor cells (Epub ahead of print) Chung, K.F., et al. Mol. Cell. Endocrinol. 333, (2010)

Neurosteroids: beginning of the story. Baulieu EE, Robel P, Schumacher M. Int. Rev. Neurobiol. 46, 1-32, (2001)

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Neuro(active)steroids actions at the neuromodulatory sigma1 (sigma1) receptor: biochemical and physiological evidences, consequences in neuroprotection. Maurice T, Grégoire C, Espallergues J. Pharmacol. Biochem. Behav. 84, 581-597, (2006)

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Neurosteroids and sigma1 receptors, biochemical and behavioral relevance. Maurice T. Pharmacopsychiatry 37, S171-!182, (2004)

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Sulfated steroids as endogenous neuromodulators. Gibbs TT, Russek SJ, Farb DH. Pharmacol. Biochem. Behav. 84, 555-567, (2006)

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Plasma concentration of myeloperoxidase enzyme in pre- and post-climacterial people: related superoxide anion generation. Békési, G., et al. Exp. Gerontol. 37, 137-48, (2001)

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Combined effects of DHEA and fadrozole on aggression and neural VIP immunoreactivity in the non-breeding male song sparrow. Wacker, D.W., et al. Horm. Behav. 53, 287-94, (2008)

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Effects of dehydroepiandrosterone on proliferation and differentiation of chromaffin progenitor cells (Epub ahead of print) Chung, K.F., et al. Mol. Cell. Endocrinol. 336, 141-148, (2011)

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Human cytochromes P450 in health and disease. Nebert DW, Wikvall K, and Miller WL Philos. Trans. R. Soc. Lond., B, Biol. Sci. 368(1612), 20120431, (2013)

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Liquid chromatography-tandem mass spectrometry analysis of human adrenal vein 19-carbon steroids before and after ACTH stimulation. Rege J, Nakamura Y, Satoh F, et al. J. Clin. Endocrinol. Metab. 98(3), 1182-8, (2013)

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Interactive effects of dehydroepiandrosterone and testosterone on cortical thickness during early brain development. Nguyen TV, McCracken JT, Ducharme S, et al. J. Neurosci. 33(26), 10840-8, (2013)

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An updated steroid benchmark set and its application in the discovery of novel nanomolar ligands of sex hormone-binding globulin. Artem Cherkasov et al J. Med. Chem. 51, 2047-56, (2008)

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Novel potent and selective bile acid derivatives as TGR5 agonists: biological screening, structure-activity relationships, and molecular modeling studies. Hiroyuki Sato et al J. Med. Chem. 51, 1831-41, (2008)

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Serum concentrations of DHEA, DHEAS, 17α-hydroxyprogesterone, Δ4-androstenedione and testosterone in children determined by TurboFlow-LC-MS/MS. Søeborg T, Frederiksen H, Fruekilde P, et al. Clin. Chim. Acta 419, 95-101, (2013)

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Fasting increases aggression and differentially modulates local and systemic steroid levels in male zebra finches. Fokidis HB, Prior NH, and Soma KK Endocrinology 154(11), 4328-39, (2013)

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Therapy of endocrine disease: Perspectives on the management of adrenal insufficiency: clinical insights from across Europe. Grossman A, Johannsson G, Quinkler M, et al. Eur. J. Endocrinol. 169(6), R165-75, (2013)

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Evaluation of urinary excretion of androgens conjugated to cysteine in human pregnancy by mass spectrometry. Fabregat A, Marcos J, Garrostas L, et al. J. Steroid Biochem. Mol. Biol. 139, 192-200, (2014)

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Variants in SULT2A1 affect the DHEA sulphate to DHEA ratio in patients with polycystic ovary syndrome but not the hyperandrogenic phenotype. Louwers YV, de Jong FH, van Herwaarden NA, et al. J. Clin. Endocrinol. Metab. 98(9), 3848-55, (2013)

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Dehydroepiandrosterone: an ancestral ligand of neurotrophin receptors. Pediaditakis I, Iliopoulos I, Theologidis I, et al. Endocrinology 156(1), 16-23, (2015)

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Estrogen-mediated regulation of steroid metabolism in rat glial cells; effects on neurosteroid levels via regulation of CYP7B1-mediated catalysis. Wicher G and Norlin M J. Steroid Biochem. Mol. Biol. 145, 21-7, (2015)

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Intracrinology in action: importance of extragonadal sex steroid biosynthesis and inactivation in peripheral tissues in both women and men. Labrie F J. Steroid Biochem. Mol. Biol. 145, 131-2, (2015)

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Dehydroepiandrosterone intra vaginal administration for the management of postmenopausal vulvovaginal atrophy. Archer DF J. Steroid Biochem. Mol. Biol. 145, 139-43, (2015)

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Sjögren's syndome and extragonadal sex steroid formation: a clue to a better disease control? Konttinen YT, Stegajev V, Al-Samadi A, et al. J. Steroid Biochem. Mol. Biol. 145, 237-44, (2015)

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Strength and function response to clinical interventions of older women categorized by weakness and low lean mass using classifications from the Foundation for the National Institute of Health sarcopenia project. Fragala MS, Dam TT, Barber V, et al. J. Gerontol. A. Biol. Sci. Med. Sci. 70(2), 202-9, (2015)

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DHEA - a precursor of ERβ ligands. Warner M and Gustafsson JA J. Steroid Biochem. Mol. Biol. 145, 245-7, (2015)

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DHEA, DHEAS and PCOS. Goodarzi MO, Carmina E, and Azziz R J. Steroid Biochem. Mol. Biol. 145, 213-25, (2015)

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DHEA effects on brain and behavior: insights from comparative studies of aggression. Soma KK, Rendon NM, Boonstra R, et al. J. Steroid Biochem. Mol. Biol. 145, 261-72, (2015)

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Combined blockade of testicular and locally made androgens in prostate cancer: a highly significant medical progress based upon intracrinology. Labrie F J. Steroid Biochem. Mol. Biol. 145, 144-56, (2015)

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All sex steroids are made intracellularly in peripheral tissues by the mechanisms of intracrinology after menopause. Labrie F J. Steroid Biochem. Mol. Biol. 145, 133-8, (2015)

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Neurobiology of DHEA and effects on sexuality, mood and cognition. Pluchino N, Drakopoulos P, Bianchi-Demicheli F, et al. J. Steroid Biochem. Mol. Biol. 145, 273-80, (2015)

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Dehydroepiandrosterone, its metabolites and ion channels. Hill M, Dušková M, and Stárka L J. Steroid Biochem. Mol. Biol. 145, 293-314, (2015)

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Methodological approach to the intracrine study and estimation of DHEA and DHEA-S using liquid chromatography-tandem mass spectrometry (LC-MS/MS). Shibata Y, Arai S, and Honma S J. Steroid Biochem. Mol. Biol. 145, 193-9, (2015)

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DHEA and cognitive function in the elderly. Maggio M, De Vita F, Fisichella A, et al. J. Steroid Biochem. Mol. Biol. 145, 281-92, (2015)

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The intracrinology of breast cancer. McNamara KM and Sasano H J. Steroid Biochem. Mol. Biol. 145, 172-8, (2015)

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Reconsideration of progression to CRPC during androgen deprivation therapy. Mizokami A and Namiki M J. Steroid Biochem. Mol. Biol. 145, 164-71, (2015)

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Dehydroepiandrosterone: a neuroactive steroid. Stárka L, Dušková M, and Hill M J. Steroid Biochem. Mol. Biol. 145, 254-60, (2015)

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DHEA and mortality: what is the nature of the association? Ohlsson C, Vandenput L, and Tivesten A J. Steroid Biochem. Mol. Biol. 145, 248-53, (2015)

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DHEA, physical exercise and doping. Collomp K, Buisson C, Lasne F, et al. J. Steroid Biochem. Mol. Biol. 145, 206-12, (2015)

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Boost energy with these everyday steps. Pacing yourself, power naps, and good nutrition help, but taking overhyped dietary supplements doesn't. Harv. Mens. Health Watch 17(11), 3, (2013)

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The effects of compounded bioidentical transdermal hormone therapy on hemostatic, inflammatory, immune factors; cardiovascular biomarkers; quality-of-life measures; and health outcomes in perimenopausal and postmenopausal women. Stephenson K, Neuenschwander PF, and Kurdowska AK Int. J. Pharm. Compd. 17(1), 74-85, (2013)

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Inhibition of Trypanosoma brucei glucose-6-phosphate dehydrogenase by human steroids and their effects on the viability of cultured parasites. Artur T Cordeiro et al Bioorg. Med. Chem. 17, 2483-9, (2009)

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Intravaginal prasterone (DHEA) provides local action without clinically significant changes in serum concentrations of estrogens or androgens. Labrie F, Martel C, Bérubé R, et al. J. Steroid Biochem. Mol. Biol. 138, 359-67, (2013)

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Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species. Denis Fourches et al Chem. Res. Toxicol. 23, 171-83, (2010)

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Ontogeny of the adrenal gland in the spiny mouse, with particular reference to production of the steroids cortisol and dehydroepiandrosterone. Quinn TA, Ratnayake U, Dickinson H, et al. Endocrinology 154(3), 1190-201, (2013)

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Potent and selective steroidal inhibitors of 17beta-hydroxysteroid dehydrogenase type 7, an enzyme that catalyzes the reduction of the key hormones estrone and dihydrotestosterone. Edith Bellavance et al J. Med. Chem. 52, 7488-502, (2009)

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Cytosolic NADPH homeostasis in glucose-starved procyclic Trypanosoma brucei relies on malic enzyme and the pentose phosphate pathway fed by gluconeogenic flux. Allmann S, Morand P, Ebikeme C, et al. J. Biol. Chem. 288(25), 18494-505, (2013)

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Androgen deprivation promotes intratumoral synthesis of dihydrotestosterone from androgen metabolites in prostate cancer. Ishizaki F, Nishiyama T, Kawasaki T, et al. Sci. Rep. 3, 1528, (2013)

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A randomized, controlled, pilot trial on the effect of dehydroepiandrosterone on ovarian response markers, ovarian response, and in vitro fertilization outcomes in poor responders. Yeung TW, Chai J, Li RH, et al. Fertil. Steril. 102(1), 108-115.e1, (2014)

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DHEA prevents mineralo- and glucocorticoid receptor-induced chronotropic and hypertrophic actions in isolated rat cardiomyocytes. Mannic T, Mouffok M, Python M, et al. Endocrinology 154(3), 1271-81, (2013)

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Androgenic biomarker prof|ling in human matrices and cell culture samples using high throughput, electrospray tandem mass spectrometry. Wilton JH, Titus MA, Efstathiou E, et al. Prostate 74(7), 722-31, (2014)

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Dehydroepiandrosterone restores right ventricular structure and function in rats with severe pulmonary arterial hypertension. Alzoubi A, Toba M, Abe K, et al. Am. J. Physiol. Heart Circ. Physiol. 304(12), H1708-18, (2013)

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Novel dehydroepiandrosterone derivatives with antiapoptotic, neuroprotective activity. Theodora Calogeropoulou et al J. Med. Chem. 52, 6569-87, (2009)

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Dehydroepiandrosterone and dehydroepiandrosterone sulfate: anabolic, neuroprotective, and neuroexcitatory properties in military men. Taylor MK Mil. Med. 178(1), 100-6, (2013)

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Role of DHEA in cardiovascular diseases. Savineau JP, Marthan R, and Dumas de la Roque E Biochem. Pharmacol. 85(6), 718-26, (2013)

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16-bromoepiandrosterone, an activator of the mammalian immune system, inhibits glucose 6-phosphate dehydrogenase from Trypanosoma cruzi and is toxic to these parasites grown in culture. Artur T Cordeiro et al Bioorg. Med. Chem. 18, 4762-8, (2010)

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Testing the sulfotransferase molecular pore hypothesis. Cook I, Wang T, Almo SC, et al. J. Biol. Chem. 288(12), 8619-26, (2013)

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Resistance training restores muscle sex steroid hormone steroidogenesis in older men. Sato K, Iemitsu M, Matsutani K, et al. FASEB J. 28(4), 1891-7, (2014)

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7α-hydroxylation of dehydroepiandrosterone does not interfere with the activation of glucocorticoids by 11β-hydroxysteroid dehydrogenase in E(t)C cerebellar neurons. Gottfried-Blackmore A, Jellinck PH, Vecchiarelli HA, et al. J. Steroid Biochem. Mol. Biol. 138, 290-7, (2013)

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Corticosterone metabolism by chicken follicle cells does not affect ovarian reproductive hormone synthesis in vitro. Rettenbacher S, Henriksen R, Groothuids TG, et al. Gen. Comp. Endocrinol. 184, 67-74, (2013)

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Nongenomic bronchodilating action elicited by dehydroepiandrosterone (DHEA) in a guinea pig asthma model. Espinoza J, Montaño LM, and Perusquía M J. Steroid Biochem. Mol. Biol. 138, 174-82, (2013)

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DHEA-mediated inhibition of the pentose phosphate pathway alters oocyte lipid metabolism in mice. Jimenez PT, Frolova AI, Chi MM, et al. Endocrinology 154(12), 4835-44, (2013)

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Binding interactions of hydroxylated polychlorinated biphenyls (OHPCBs) with human hydroxysteroid sulfotransferase hSULT2A1. Ekuase EJ, Lehmler HJ, Robertson LW, et al. Chem. Biol. Interact. 212, 56-64, (2014)

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Catechin gallates are NADP+-competitive inhibitors of glucose-6-phosphate dehydrogenase and other enzymes that employ NADP+ as a coenzyme. Eui Seok Shin et al Bioorg. Med. Chem. 16, 3580-6, (2008)

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Differential effects of dehydroepiandrosterone and testosterone in prostate and colon cancer cell apoptosis: the role of nerve growth factor (NGF) receptors. Anagnostopoulou V, Pediaditakis I, Alkahtani S, et al. Endocrinology 154(7), 2446-56, (2013)

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Relationship of adiponectin with sex hormone levels in adolescents. Riestra P, Garcia-Anguita A, Ortega L, et al. Horm. Res. Paediatr. 79(2), 83-7, (2013)

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Dehydroepiandrosterone exerts antiglucocorticoid action on human preadipocyte proliferation, differentiation, and glucose uptake. McNelis JC, Manolopoulos KN, Gathercole LL, et al. Am. J. Physiol. Endocrinol. Metab. 305(9), E1134-44, (2013)

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Associations of urinary 6-sulfatoxymelatonin with demographics, body mass, sex steroids, and lifestyle factors in preschool Japanese children. Wada K, Nakamura K, Tamai Y, et al. Ann. Epidemiol. 23(2), 60-5, (2013)

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Dehydroepiandrosterone supplementation in elderly men: a meta-analysis study of placebo-controlled trials. Corona G, Rastrelli G, Giagulli VA, et al. J. Clin. Endocrinol. Metab. 98(9), 3615-26, (2013)

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Problematic drinking and physiological responses among female college students. Wemm S, Fanean A, Baker A, et al. Alcohol 47(2), 149-57, (2013)

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Syntheses of immunomodulating androstanes and stigmastanes: comparison of their TNF-alpha inhibitory activity. Javier A Ramírez et al Bioorg. Med. Chem. 15, 7538-44, (2007)

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Endocrine regulation of airway contractility is overlooked. Bossé Y J. Endocrinol. 222(2), R61-73, (2014)

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To determine the cytotoxicity of chlorambucil and one of its nitro-derivatives, conjugated to prasterone and pregnenolone, towards eight human cancer cell-lines. Shervington, L. A.; et al. Eur. J. Med. Chem. 44, 2944, (2009)

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TGFβ1 alters androgenic metabolites and hydroxysteroid dehydrogenase enzyme expression in human prostate reactive stromal primary cells: Is steroid metabolism altered by prostate reactive stromal microenvironment? Piao YS, Wiesenfeld P, Sprando R, et al. J. Steroid Biochem. Mol. Biol. 138, 206-13, (2013)

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[The alternative androgen synthesis pathway in humans]. Kamrath C, Hartmann MF, and Wudy S Klin. Padiatr. 225(1), 3-7, (2013)

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Assessment of the potential of polyphenols as a CYP17 inhibitor free of adverse corticosteroid elevation. Lin CJ, Cheng LC, Lin TC, et al. Biochem. Pharmacol. 90(3), 288-96, (2014)

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Androgen synthesis in the gonadotropin-suppressed human testes can be markedly suppressed by ketoconazole. Roth MY, Nya-Ngatchou JJ, Lin K, et al. J. Clin. Endocrinol. Metab. 98(3), 1198-206, (2013)

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First synthesis of 7alpha- and 7beta-amino-DHEA, dehydroepiandrosterone (DHEA) analogues and preliminary evaluation of their cytotoxicity on Leydig cells and TM4 Sertoli cells. Marc-Antoine Bazin et al Bioorg. Med. Chem. 15, 3152-60, (2007)

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Glucose-6-phosphate dehydrogenase plays a critical role in hypoxia-induced CD133+ progenitor cells self-renewal and stimulates their accumulation in the lungs of pulmonary hypertensive rats. Chettimada S, Joshi SR, Alzoubi A, et al. Am. J. Physiol. Lung Cell. Mol. Physiol. 307(7), L545-56, (2014)

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Vitamin D receptor agonist EB1089 is a potent regulator of prostatic "intracrine" metabolism. Doherty D, Dvorkin SA, Rodriguez EP, et al. Prostate 74(3), 273-85, (2014)

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Silencing diacylglycerol kinase-theta expression reduces steroid hormone biosynthesis and cholesterol metabolism in human adrenocortical cells. Cai K, Lucki NC, and Sewer MB Biochim. Biophys. Acta 1841(4), 552-62, (2014)

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Dehydroepiandrosterone protects endothelial cells against inflammatory events induced by urban particulate matter and titanium dioxide nanoparticles. Huerta-García E, Montiél-Dávalos A, Alfaro-Moreno E, et al. Biomed Res. Int. 2013, 382058, (2013)

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Modulation of higher-primate adrenal androgen secretion with estrogen-alone or estrogen-plus-progesterone intervention. Conley AJ, Stanczyk FZ, Morrison JH, et al. Menopause 20(3), 322-8, (2013)

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Dehydroepiandrosterone modulates T-cell response after major abdominal surgery. Pratschke S, von Dossow-Hanfstingl V, Dietz J, et al. J. Surg. Res. 189(1), 117-25, (2014)

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Dehydroepiandrosterone post-transcriptionally modifies CYP1A2 induction involving androgen receptor. Belic A, Tóth K, Vrzal R, et al. Chem. Biol. Interact. 203(3), 597-603, (2013)

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Enhanced biotransformation of dehydroepiandrosterone to 3β,7α,15α-trihydroxy-5-androsten-17-one with Gibberella intermedia CA3-1 by natural oils addition. Li H, Fu Z, Li H, et al. J. Ind. Microbiol. Biotechnol. 41(10), 1497-504, (2014)

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[Local estrogen therapy--clinical implications--2012 update]. Kokot-Kierepa M, Bartuzi A, Kulik-Rechberger B, et al. Ginekol. Pol. 83(10), 772-7, (2012)

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[Treatment of adrenal deficiency: To what issues? By which therapeutic means?]. Reznik Y Presse Med. 43(4 Pt 1), 438-43, (2014)

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Effect of argan and olive oil consumption on the hormonal profile of androgens among healthy adult Moroccan men. Derouiche A, Jafri A, Driouch I, et al. Nat. Prod. Commun. 8(1), 51-3, (2013)

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Neurosteroids dehydroepiandrosterone and its sulfate in individuals with personality disorders convicted of serious violent crimes. Gavrilova VA, Ivanova SA, Gusev SI, et al. Bull. Exp. Biol. Med. 154(1), 89-91, (2012)

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Steroid cell tumor of the ovary in a pregnant woman whose androgenic symptoms were masked by pregnancy. Oz M, Ozgü E, Türker M, et al. Arch. Gynecol. Obstet. 290(1), 131-4, (2014)

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Androgens concentrations and second-to fourth-digit ratio (2D:4D) in girls with congenital adrenal hyperplasia (21-hydroxylase deficiency). Oswiecimska JM, Ksiazek A, Sygulla K, et al. Neuro Endocrinol. Lett. 33(8), 787-91, (2012)

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Effects of dehydroepiandrosterone in amphetamine-induced schizophrenia models in mice. Kilic FS, Kulluk D, and Musmul A Neurosciences (Riyadh.) 19(2), 100-5, (2014)

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A rare granulosa cell tumor presentation with virilization and cystic adnexal mass on three-dimensional ultrasound: a case report. Tanouye S, Gada R, Famuyide A, et al. J. Reprod. Med. 59(7-8), 421-4, (2014)

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Neonatal free testosterone and decreased head circumference in females: evidence of reduced inactivation of testosterone in the brain. Sanders BK Dev. Med. Child Neurol. 55(6), 580, (2013)

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No evidence to support the concept that low serum dehydroepiandrosterone (DHEA) sulfate (s) levels are associated with less oocyte production or lower pregnancy rates. Borman E, Check JH, Mitchell-Williams J, et al. Clin. Exp. Obstet. Gynecol. 39(4), 429-31, (2012)

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Merck 14,2871

Beil. 8,IV,994

Aldrich MSDS 1, 555:B / Corp MSDS 1 (1), 1023:B / FT-IR 2 (3), 4225:B / FT-IR 1 (2), 1050:D / FT-NMR 1 (3), 573:B / IR-Spectra (2), 1279:E / IR-Spectra (3), 1495:F / NMR-Reference 2 (2), 922:A / RegBook 1 (2), 2857:M / Sigma FT-IR 1 (1), 1227:B / Structure Index 1, 457:D:8

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