19-hydroxy-4-androsten-17-one, also known as **19-OH-4-androstene-17-one** or **19-hydroxytestosterone**, is a naturally occurring steroid hormone that is a precursor to testosterone. It is important for research for the following reasons:
**1. Role in Testosterone Synthesis:**
* **Precursor to testosterone:** 19-hydroxy-4-androsten-17-one is an important intermediate in the biosynthesis of testosterone. It is converted to testosterone through the enzymatic action of 19-hydroxysteroid dehydrogenase (19-HSD).
* **Regulation of Testosterone Production:** The concentration of 19-hydroxy-4-androsten-17-one can influence the rate of testosterone production. Studies have shown that its levels are higher in males compared to females, reflecting the higher levels of testosterone in males.
**2. Potential Therapeutic Applications:**
* **Treatment of Hypogonadism:** Research is exploring its potential role in treating hypogonadism, a condition characterized by low testosterone levels.
* **Anabolic Effects:** Due to its structural similarity to testosterone, it has potential anabolic (muscle-building) effects. However, further research is needed to determine its safety and efficacy for therapeutic use.
**3. Research into Steroid Metabolism:**
* **Understanding Steroid Pathways:** The study of 19-hydroxy-4-androsten-17-one helps researchers understand the intricate pathways of steroid metabolism.
* **Investigating Enzyme Activity:** It provides a model system for studying the activity of enzymes involved in steroid biosynthesis, such as 19-HSD.
**4. Applications in Sports Medicine and Doping Control:**
* **Doping Detection:** 19-hydroxy-4-androsten-17-one is a potential marker for steroid use in sports, as its presence may indicate the use of testosterone precursors or synthetic steroids.
* **Anti-Doping Research:** Research focuses on developing methods to detect and prevent the use of 19-hydroxy-4-androsten-17-one and other steroid precursors for performance enhancement.
**It's important to note that 19-hydroxy-4-androsten-17-one is a powerful hormone and should only be used under strict medical supervision.**
19-hydroxy-4-androsten-17-one: structure given in first source; potential competitive inhibitor of estrogen biosynthesis [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
| ID Source | ID |
|---|---|
| PubMed CID | 129500 |
| CHEMBL ID | 1629805 |
| SCHEMBL ID | 3361320 |
| MeSH ID | M0166574 |
| Synonym |
|---|
| bdbm50332808 |
| (8r,9s,10s,13s,14s)-10-(hydroxymethyl)-13-methyl-2,3,7,8,9,10,11,12,13,14,15,16-dodecahydro-1h-cyclopenta[alpha]phenanthren-17(6h)-one |
| 19-hado |
| (8r,9s,10s,13s,14s)-10-(hydroxymethyl)-13-methyl-1,2,3,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one |
| CHEMBL1629805 , |
| 121739-39-7 |
| androst-4-en-17-one, 19-hydroxy- |
| 19-hydroxy-4-androsten-17-one |
| SCHEMBL3361320 |
| 19-hydroxyandrost-4-en-17-one |
| DTXSID60923948 |
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Aromatase | Homo sapiens (human) | IC50 (µMol) | 0.1227 | 0.0000 | 1.2904 | 10.0000 | AID53564; AID53576; AID548357 |
| Aromatase | Homo sapiens (human) | Ki | 0.0104 | 0.0000 | 0.6046 | 9.5010 | AID1270838; AID53398; AID53740 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Aromatase | Homo sapiens (human) | pIC50 | 1.3100 | 1.3100 | 1.3435 | 1.3770 | AID548357 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Process | via Protein(s) | Taxonomy |
|---|---|---|
| negative regulation of chronic inflammatory response | Aromatase | Homo sapiens (human) |
| steroid biosynthetic process | Aromatase | Homo sapiens (human) |
| estrogen biosynthetic process | Aromatase | Homo sapiens (human) |
| androgen catabolic process | Aromatase | Homo sapiens (human) |
| syncytium formation | Aromatase | Homo sapiens (human) |
| negative regulation of macrophage chemotaxis | Aromatase | Homo sapiens (human) |
| sterol metabolic process | Aromatase | Homo sapiens (human) |
| female genitalia development | Aromatase | Homo sapiens (human) |
| mammary gland development | Aromatase | Homo sapiens (human) |
| uterus development | Aromatase | Homo sapiens (human) |
| prostate gland growth | Aromatase | Homo sapiens (human) |
| testosterone biosynthetic process | Aromatase | Homo sapiens (human) |
| positive regulation of estradiol secretion | Aromatase | Homo sapiens (human) |
| female gonad development | Aromatase | Homo sapiens (human) |
| response to estradiol | Aromatase | Homo sapiens (human) |
| [Information is prepared from geneontology information from the June-17-2024 release] | ||
| Process | via Protein(s) | Taxonomy |
|---|---|---|
| iron ion binding | Aromatase | Homo sapiens (human) |
| steroid hydroxylase activity | Aromatase | Homo sapiens (human) |
| electron transfer activity | Aromatase | Homo sapiens (human) |
| oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen | Aromatase | Homo sapiens (human) |
| oxygen binding | Aromatase | Homo sapiens (human) |
| heme binding | Aromatase | Homo sapiens (human) |
| aromatase activity | Aromatase | Homo sapiens (human) |
| [Information is prepared from geneontology information from the June-17-2024 release] | ||
| Process | via Protein(s) | Taxonomy |
|---|---|---|
| endoplasmic reticulum | Aromatase | Homo sapiens (human) |
| endoplasmic reticulum membrane | Aromatase | Homo sapiens (human) |
| membrane | Aromatase | Homo sapiens (human) |
| endoplasmic reticulum | Aromatase | Homo sapiens (human) |
| [Information is prepared from geneontology information from the June-17-2024 release] | ||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID548357 | Inhibition of human placental aromatase | 2010 | European journal of medicinal chemistry, Dec, Volume: 45, Issue:12 | Molecular docking and QSAR study on steroidal compounds as aromatase inhibitors. |
| AID1270838 | Competitive inhibition of human aromatase extracted from placental microsomes by Dixon plot analysis in presence of [1,2-3H]androstenedione | 2015 | European journal of medicinal chemistry, Nov-13, Volume: 105 | Developing steroidal aromatase inhibitors-an effective armament to win the battle against breast cancer. |
| AID53576 | Inhibition of 1 uM [1-beta-3H]-androstenedione binding to human placental microsome Cytochrome P450 19A1 | 1991 | Journal of medicinal chemistry, Aug, Volume: 34, Issue:8 | Synthesis and biochemical studies of 16- or 19-substituted androst-4-enes as aromatase inhibitors. |
| AID53398 | Apparent inhibition constant for aromatase inhibition, was obtained by Dixon plot | 2001 | Journal of medicinal chemistry, Nov-22, Volume: 44, Issue:24 | Role of hydrophilic interaction in binding of hydroxylated 3-deoxy C(19) steroids to the active site of aromatase. |
| AID53564 | Inhibition of aromatase activity in human placental microsomes determined by radiometric assay | 2001 | Journal of medicinal chemistry, Nov-22, Volume: 44, Issue:24 | Role of hydrophilic interaction in binding of hydroxylated 3-deoxy C(19) steroids to the active site of aromatase. |
| AID53740 | Binding affinity for human placental microsome cytochrome P450 19A1 with 1 uM [1-beta-3H]-androstenedione | 1991 | Journal of medicinal chemistry, Aug, Volume: 34, Issue:8 | Synthesis and biochemical studies of 16- or 19-substituted androst-4-enes as aromatase inhibitors. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 1 (20.00) | 18.7374 |
| 1990's | 1 (20.00) | 18.2507 |
| 2000's | 1 (20.00) | 29.6817 |
| 2010's | 2 (40.00) | 24.3611 |
| 2020's | 0 (0.00) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.
| This Compound (12.76) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 1 (20.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 4 (80.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||