Dehydroepiandrosterone

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Dehydroepiandrosterone

Dehydroepiandrosterone


3ß-hydroxy-5-androsten-17-one
CAS number 53-43-0	ATC code A14AA07
Chemical formula	C₁₉H₂₈O₂
Molecular weight	288.43
Bioavailability	?%
Metabolism	Hepatic
Elimination half-life	12 hours
Excretion	Urinary:?%
Pregnancy category	?
Legal status	Commercially available (US)
Routes of administration	Oral
Melting point	146–151°C
Specific rotation ^*_D

Dehydroepiandrosterone (DHEA), is a natural steroid hormone produced from cholesterol by the adrenal glands found atop of the kidneys in the human body. DHEA is also produced in the gonads, adipose tissue and the brain. DHEA is structurally similar to, and is a precursor of, androstenedione, testosterone and estrogen. It is the most abundant hormone in the human body. Synonymes for Dehydroepiandrosterone are: Dehydroisoandrosterone; 3beta-Hydroxy-5-androsten-17-one; 3beta-Hydroxyandrost-5-en-17-one; Androstenol; Androstenolone; Dehydroisoandrosterone; Hydroxyandrost-5-en-17-one; Prasterone; trans-Dehydroandrosterone. Brand names for DHEA include Prastera® and Fidelin®.

DHEA-DHEAS

Dehydroepiandrosterone sulfate (DHEAS) is the sulfated version of DHEA, - this conversion is reversibly catalyzed by sulfotransferase (SULT2A1) primarily in the adrenals, the liver, and small intestines. In blood, most DHEA is found as DHEAS with levels that are about 300 times higher than free DHEA. Orally ingested DHEA is converted to its sulfate when passing through intestines and liver. While DHEA levels reach their peak in the early morning hours, DHEAS levels show no diurnal variation. DHEAS is biologically active only after its sulfate group has been split and it becomes DHEA again.

From a practical point measurement of DHEAS is preferable to DHEA as levels are more stable.

Production

DHEA is produced from cholesterol through two cytochrome P450 enzymes. Cholesterol is converted to pregnenolone by the enzyme P450 scc (side chain cleavage) and then another enzyme P450c17 (CYP17A) converts pregnenolone to 17α-Hydroxypregnenolone and then to DHEA. In humans DHEA is the dominant steroid hormone and precursor of all sex steroids. Humans produce DHEA in greater quantity than any other species. Even non-human primates have not much more than 10% the relative serum level of DHEA seen in humans. The fact that rodents produce so little DHEA makes the results of experiments conducted with these laboratory animals very controversial.

DHEA production is very high during fetal life by the fetal adrenal glands, declines after birth and remains low during childhood. Production begins around 6 years of age, increasing in quantity until peaking in early adulthood, around the age of 25, and declines afterwards to approximately 10% of peak levels by age 80. It is theorized by some that this decline may be due to reduced oxygen and glucose supply to the adrenal glands as a result of age-related atherosclerosis.

Role of DHEA

In a simple view DHEA can be understood as a prohormone for the sex steroids. Its DHEAS variation may be looked at as buffer and reservoir. Its production in the brain suggests that is also has a role as a neurosteroid. As most DHEA is produced by the zona reticularis of the adrenal, it is argued that there is a role in the immune and stress response. DHEA may have more biologic roles.

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 normal or mildly elevated levels of DHEAS.

Effects of DHEA

Studies have shown that DHEA is useful in patients with systemic lupus erythematosus. An application of the evidence was reviewed by the FDA in 2001 and is available online.FDA document regading DHEA and SLE This review also shows that cholesterol and other serum lipids decrease with the use of DHEA.

Supplementation with DHEA has been shown to decrease insulin resistance.Kawano H, Yasue H, Kitagawa A, et al. Dehydroepiandrosterone supplementation improves endothelial function and insulin sensitivity in men. J Clin Endocrinol Metab. 2003 Jul;88(7):3190-5.

Long term supplementation has been shown to improve mood and relieve depression.Wolkowitz OM, Reus VI, Roberts E, et al. Antidepressant and cognition-enhancing effects of DHEA in major depression. Ann NY Acad Sci. 1995 Dec 29;774:337-9

Disputed effects of DHEA

The significance of the hormone in health and disease is not fully established. It is postulated that DHEA supplements are beneficial in the prevention of:

It is also commercially advertised that DHEA:

helps decrease insulin resistance
improves fat metabolism
increases immune system function
has anti-aging properties
increases lean muscle mass

7-Keto™ DHEA, a recently identified natural metabolite of dehydroepiandrosterone (DHEA) is claimed to be both more effective and safer than DHEA because it does not convert itself into testosterone or estrogens in the body.

DHEA and DHEAS are readily available in the United States, but not in many other countries.

Precautions

Some assert that DHEA should not be supplemented outside specialist centres under careful observation of experts in the field of endocrinology.

Side effects may include:

extensive growth of body hair, or hirsutism
male pattern baldness
acne

Contraindication

As DHEAS and DHEA are converted to sex steroids, their use is contraindicated in patients with any cancer that is estrogen or testosterone dependent.

Increasing endogenous DHEA production

Regular exercise is known to the body.Eur J Appl Physiol Occup Physiol 1998 Oct;78(5):466-71Eur J Appl Physiol. 2001 Jul;85(1- 2):177-84J Gerontol A Biol Sci Med Sci. 2002 Apr;57(4):B158-65 Caloric restriction has also been shown to increase DHEA in primates.Exp Gerontol. 2003 Jan-Feb; 38(1-2):35-46

References

External links

The DHEA Debate: A critical review of experimental data (Published 2004)
DHEA: Ignore the Hype (Published 1996)
DHEA Hormone Replacement
What the skeptic dictionary has to say on DHEA

Androgens

DHEA | Déhydroépiandrostérone | Dehydroepiandrosteron

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