4294
T3D4240
Androstenedione
Androstenedione is a delta-4 19-carbon steroid that is produced not only in the testis, but also in the ovary and the adrenal cortex. Depending on the tissue type, androstenedione can serve as a precursor to testosterone as well as estrone and estradiol. It is the common precursor of male and female sex hormones. Some androstenedione is also secreted into the plasma, and may be converted in peripheral tissues to testosterone and estrogens. Androstenedione originates either from the conversion of dehydroepiandrosterone or from 17-hydroxyprogesterone. It is further converted to either testosterone or estrone. The production of adrenal androstenedione is governed by ACTH, while production of gonadal androstenedione is under control by gonadotropins.
63-05-8
6128
C19H26O2
White powder.
170 - 173°C
0.0578 mg/mL
Endogenous, ingestion
Androstenedione is converted to testosterone and estrogen, and when taken in sufficient quantities androstenedione can cause unwanted masculinizing and feminizing effects. Androstenedione is considered an androgenic steroid precursor because testosterone is an androgen or male hormone. In males, conversion of androstenedione to testosterone requires the enzyme 17β-hydroxysteroid dehydrogenase. In females, conversion of androstenedione to estrogen (e.g., estrone and estradiol) requires the enzyme aromatase.
Androstenedione originates either from the conversion of dehydroepiandrosterone or from 17-hydroxyprogesterone. It is further converted to either testosterone or estrone. The production of adrenal androstenedione is governed by ACTH, while production of gonadal androstenedione is under control by gonadotropins. In males, conversion of androstenedione to testosterone requires the enzyme 17β-hydroxysteroid dehydrogenase. In females, conversion of androstenedione to estrogen (e.g., estrone and estradiol) requires the enzyme aromatase.
No indication of carcinogenicity to humans (not listed by IARC).
Androstenedione was legally defined as an anabolic steroid by the FDA in 2004. It poses significant health risks commonly associated with steroids. The side effects for men include breast development, behavioral changes, heart disease, and more. Side effects for women are similar to the side effects from anabolic steroids in that their voices will deepen and they may grow facial hair since both occur from an increase level of testosterone. Another side effect of androstenedione is male pattern baldness. The main psychological side effect of androstenedione is depression. Mood swings are also common. Chronically high levels of androstenedione are associated with male pseudohermaphrodism with gynecomastia, Adrenal Hyperplasia Type 3 and Aromatase deficiency.
Breast development (in men), behavioral changes, heart disease, male pattern baldness and depression. Side effects for women include a deepening and they may grow facial hair. In children or fetuses high levels of androstenedione (CAH) can lead to a number of changes. Females with congenital adrenal hyperplasia are born with an enlarged clitoris and normal internal reproductive tract structures. Males have normal genitals at birth. CAH causes abnormal growth for both sexes; patients will be tall as children and short as adults. Females develop male characteristics, and males experience premature sexual development.
2014-08-29T05:59:33Z
2014-12-24T20:26:43Z
Androstenedione
C00280
16422
ANDROST4ENE
DB01536
ASD
true
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
C19H26O2
InChI=1S/C19H26O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-16H,3-10H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1
InChIKey=AEMFNILZOJDQLW-QAGGRKNESA-N
286.4085
286.193280076
Endogenous
Solid
2.75
HMDB00053
CHEMBL274826
5898
<p>Angela M. H. Brodie, Harry J. Brodie, David A. Marsh, “Ester derivatives of 4-hydroxy-4-androstene-3,17-dione and a method for inhibiting estrogen biosynthesis.” U.S. Patent US4235893, issued October, 1962.</p>