Dehydroepiandrosterone

Title: Dehydroepiandrosterone
CAS Registry Number: 53-43-0
CAS Name: (3b)-3-Hydroxyandrost-5-en-17-one
Additional Names: prasterone; dehydroisoandrosterone; trans-dehydroandrosterone; D5-androsten-3b-ol-17-one; DHEA
Molecular Formula: C19H28O2
Molecular Weight: 288.42
Percent Composition: C 79.12%, H 9.79%, O 11.09%
Literature References: Major secretory steroidal product of the adrenal gland; secretion progressively declines with aging. May have estrogen- or androgen-like effects depending on the hormonal milieu. Intracellularly converted to androstenedione, q.v. Isoln from male urine: Butenandt, Tscherning, Z. Physiol. Chem. 229, 167 (1934); Butenandt, Dannenbaum, ibid. 192. Prepn from cholesterol: Butenandt et al., ibid. 237, 57 (1935); Ruzicka, Wettstein, Helv. Chim. Acta 18, 986 (1935); Wallis, Fernholz, J. Am. Chem. Soc. 57, 1379, 1504 (1935); Schoeller et al., Naturwissenschaften 23, 337 (1935); from sitosterol: Oppenauer, Nature 135, 1039 (1935). High yield prepn: H. Hosoda et al., J. Org. Chem. 38, 4209 (1973). Metabolism study: P. Knapstein et al. Acta Endocrinol. 58, 261 (1968). Toxicity study of the sulfate: M. Yahara et al., J. Toxicol. Sci. 2, 161 (1977). Clinical evaluation in hormone replacement therapy: A. J. Morales et al., J. Clin. Endocrinol. Metab. 78, 1360 (1994); in systemic lupus erythematosus: R. F. van Vollenhoven et al., Arthritis Rheum. 38, 1826 (1995). Review of physiological importance: P. Ebeling, V. A. Koivisto, Lancet 343, 1479-1481 (1994). Symposium on role in aging: Ann. N.Y. Acad. Sci. 774, 1-350 (1995). Review of therapeutic potential: B. Allolio, W. Arlt, Trends Endocrinol. Metab. 13, 288-294 (2002).
Properties: Dimorphous, needles, mp 140-141°; leaflets, mp 152-153°. [a]18D +10.9° (c = 0.4 in alc). Pptd by digitonin. Sol in benzene, alcohol, ether; sparingly sol in chloroform, petr ether.
Melting point: mp 140-141°; mp 152-153°
Optical Rotation: [a]18D +10.9° (c = 0.4 in alc)
Derivative Type: Sulfate
CAS Registry Number: 651-48-9
Additional Names: DHEAS
Molecular Formula: C19H28O5S
Molecular Weight: 368.49
Percent Composition: C 61.93%, H 7.66%, O 21.71%, S 8.70%
Literature References: Hydrophilic storage form that circulates in the blood.
Derivative Type: Sodium sulfate
CAS Registry Number: 1099-87-2
Additional Names: Sodium dehydroepiandrosterone sulfate
Trademarks: Astenile (Recordati); Mylis (Kanebo)
Molecular Formula: C19H27NaO5S
Molecular Weight: 390.47
Percent Composition: C 58.44%, H 6.97%, Na 5.89%, O 20.49%, S 8.21%
Properties: White cryst powder, mp 154° (dec). Sol in methanol, slightly sol in water, abs ethanol. Practically insol in acetone, chloroform, benzene.
Melting point: mp 154° (dec)
Therap-Cat: In treatment of menopausal syndrome.
Keywords: Androgen.
Dehydroergosterol Delapril Delavirdine Delmadinone Acetate Delmopinol

Dehydroepiandrosterone
DHEA.png
Dehidroepiandrosterona3D.png
Systematic (IUPAC) name
(3S,8R,9S,10R,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one
Clinical data
Legal status Prescription Only (S4) (AU) Rx Only (CA) OTC (US)
Routes Oral
Pharmacokinetic data
Metabolism Hepatic
Half-life 12 hours
Excretion Urinary:?%
Identifiers
CAS number 53-43-0 YesY
ATC code A14AA07
G03EA03 (combination with estrogen)
PubChem CID 5881
IUPHAR ligand 2370
DrugBank DB01708
ChemSpider 5670 YesY
UNII 459AG36T1B YesY
ChEBI CHEBI:28689 YesY
ChEMBL CHEMBL90593 YesY
Synonyms (3β)-3-Hydroxyandrost-5-en-17-one
Chemical data
Formula C19H28O2 
Mol. mass 288.424 g/mol
Physical data
Melt. point 148.5 °C (299 °F)
 YesY (what is this?)  (verify)

Dehydroepiandrosterone (DHEA, more correctly didehydroepiandrosterone; brand name Ovigyn-d, Ovaflo, Fidelin, Ovomax), also known as androstenolone or prasterone (INN), as well as 3β-hydroxyandrost-5-en-17-one or 5-androsten-3β-ol-17-one, is an important endogenous steroid hormone.[1] It is the most abundant circulating steroid in humans,[2] in whom it is produced in the adrenal glands,[3] the gonads, and the brain,[4] where it functions predominantly as a metabolic intermediate in the biosynthesis of the androgen and estrogen sex steroids.[1][5] However, DHEA also has a variety of potential biological effects in its own right, binding to an array of nuclear and cell surface receptors,[6] and acting as a neurosteroid.[7]