2871. Dehydroepiandrosterone

Nomenclature

CAS number: 53-43-0
(3β)-3-Hydroxyandrost-5-en-17-one; prasterone; dehydroisoandrosterone; trans-dehydroandrosterone; Δ5-androsten-3β-ol-17-one; DHEA; Prestara (Genelabs).
C19H28O2; mol wt 288.42.
C 79.12%, H 9.79%, O 11.09%.

Description and 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). 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 in aging: B. Allolio, W. Arlt, Trends Endocrinol. Metab. 13, 288-294 (2002); of clinical experience in lupus: P. Kocis, Am. J. Health Syst. Pharm. 63, 2201-2210 (2006).

Chemical structure

Properties

Dimorphous, needles, mp 140-141°; leaflets, mp 152-153°. [α]18D +10.9° (c = 0.4 in alc). Pptd by digitonin. Sol in benzene, alcohol, ether; sparingly sol in chloroform, petr ether.

Derivative

Sulfate.

Nomenclature

CAS number: 651-48-9
DHEAS.
C19H28O5S; mol wt 368.49.
C 61.93%, H 7.66%, O 21.71%, S 8.70%.

Description and references

Hydrophilic storage form that circulates in the blood.

Derivative

Sodium sulfate.

Nomenclature

CAS number: 1099-87-2
Sodium dehydroepiandrosterone sulfate; Astenile (Recordati); Mylis (Organon).
C19H27NaO5S; mol wt 390.47.
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.

Therapeutic Category

In treatment of menopausal syndrome and systemic lupus erythematosus (SLE).

Keywords

Androgen