Androstenedione
[CAS# 63-05-8]

Identification

• Classification: Analytical chemistry >> Standard >> Traditional chinese medicine standard
• Name: Androstenedione
• Synonyms: Androst-4-ene-3,17-dione; 4-Androstenedione; 4-Androstene-3,17-dione
• Molecular Formula: C₁₉H₂₆O₂
• Molecular Weight: 286.41
• CAS Registry Number: 63-05-8
• EC Number: 200-554-5
• SMILES: C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CCC4=O)C

Properties

• Melting point: 170-173 °C

Safety Data

• Hazard Symbols: HGS07;HGS08 Danger
• Risk Statements: H302-H351-H360-H362
• Safety Statements: P203-P260-P263-P264-P270-P280-P301+P317-P318-P330-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Reproductive toxicity	Repr.	1A	H360
Carcinogenicity	Carc.	2	H351
Reproductive toxicity	Lact.	-	H362
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Carcinogenicity	Carc.	1B	H350

• Controlled Substance: DEA Drug Code Number: 4000

Discovery and Applications

Androstenedione is a naturally occurring steroid hormone and precursor of testosterone and estrone, with important implications in endocrinology, medicine, and sports. Androstenedione was first isolated and identified in the early 1930s by Adolf Butenandt and Kurt Tscherning through purification of urine extracts. It belongs to the androgen family and is primarily produced from cholesterol in the adrenal and gonadal glands through a series of enzymatic reactions.

In humans, androstenedione is synthesized in the adrenal cortex and gonadal glands (testes in males, ovaries in females) under the control of adrenocorticotropic hormone (ACTH) and gonadotropins, respectively. It is a precursor for the biosynthesis of testosterone and estrone, which are key hormones affecting sexual development, reproductive function, and overall health.

Androstenedione plays multiple key roles in human physiology: It is a precursor for the biosynthesis of testosterone, a major male sex hormone essential for the development of secondary sexual characteristics, muscle growth, and bone density. In women, androstenedione is converted to estrone in peripheral tissues, exerting estrogenic effects that are essential for regulating the menstrual cycle and reproductive health. It participates in various metabolic pathways, affecting lipid metabolism, protein synthesis, and energy production.

Androstenedione and its derivatives are used in hormone replacement therapy (HRT) to treat conditions associated with hormone deficiency, such as hypogonadism, where treatment involves replenishing testosterone levels in men and estrogen levels in women to restore hormone balance and relieve symptoms. Androstenedione derivatives are sometimes used to relieve menopausal symptoms, such as hot flashes and vaginal dryness, by replenishing falling estrogen levels.

Androstenedione research extends to exploring its potential for use in the following areas: Synthetic derivatives of androstenedione are used in sports and medicine to enhance muscle growth, but their use is regulated and monitored due to potential health risks and doping concerns. Studies have investigated the role of androstenedione and its metabolites in hormone-sensitive cancers, such as breast and prostate cancer, where hormone therapy is intended to modulate hormone receptor activity and tumor growth.

The use of androstenedione and its analogs in sports has sparked controversy due to their potential for abuse as performance-enhancing drugs. Regulatory bodies such as the World Anti-Doping Agency (WADA) have banned their use in competitive sports to maintain fairness and safety.

References

1979. The use of plasma androstenedione in monitoring therapy of patients with congenital adrenal hyperplasia. The Journal of Pediatrics, 95(1).
DOI: 10.1016/s0022-3476(79)80078-5

1990. The gene for 17beta-hydroxysteroid dehydrogenase maps to human chromosome 17, bands q12–q21, and shows an RFLP with ScaI. Human Genetics, 85(5).
DOI: 10.1007/bf00194219

2003. Congenital Adrenal Hyperplasia. Pediatric Endocrinology.
DOI: 10.1007/978-1-59259-336-1_13