11β-Hydroxydihydrotestosterone and 11-ketodihydrotestosterone, novel C19 steroids with androgenic activity: A putative role in castration resistant prostate cancer?
Abstract
Adrenal C19 steroids, dehydroepiandrostenedione (DHEA(S)) and androstenedione (A4), play a critical role in castration resistant prostate cancer (CRPC) as they are metabolised to dihydrotestosterone (DHT), via testosterone (T), or via the alternate 5α-dione pathway, bypassing T. Adrenal 11OHA4 metabolism in CRPC is, however, unknown. We present a novel pathway for 11OHA4 metabolism in CRPC leading to the production of 11ketoT (11KT) and novel 5α-reduced C19 steroids - 11OH-5α-androstanedione, 11keto-5α-androstanedione, 11OHDHT and 11ketoDHT (11KDHT). The pathway was validated in the androgen-dependent prostate cancer cell line, LNCaP. Androgen receptor (AR) transactivation studies showed that while 11KT and 11OHDHT act as a partial AR agonists, 11KDHT is a full AR agonist exhibiting similar activity to DHT at 1nM. Our data demonstrates that, while 11OHA4 has negligible androgenic activity, its metabolism to 11KT and 11KDHT yields androgenic compounds which may be implicated, together with A4 and DHEA(S), in driving CRPC in the absence of testicular T.
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11KT is a substrate for 5α-reductases.
“Furthermore, similar to the conversion of T to dihydrotestosterone (DHT) in target tissues, 11KT is a substrate for 5α-reductases (28).”
From 24-Hour Profiles of 11-Oxygenated C19 Steroids and Δ5-Steroid Sulfates during Oral and Continuous Subcutaneous Glucocorticoids in 21-Hydroxylase Deficiency (2021) · cites this paper as [28]
11ketotestosterone and 11-keto-DHT bind and activate the androgen receptor.
“including, 11ketotestosterone and 11-keto-DHT, androgens that bind and activate the androgen receptor.128,129”
From Congenital adrenal hyperplasia (2017) · cites this paper as [129]
Activation/inactivation of glucocorticoids and 11-oxygenated androgens work in antiparallel manner, with 11β-hydroxy derivative being active glucocorticoid, while 11-keto androgens are more potent than their 11β-hydroxy counterparts.
“Interestingly, activation/inactivation of glucocorticoids and 11-oxygenated androgens work in an antiparallel manner, with the 11β-hydroxy derivative being the active glucocorticoid [74,75], while the 11-keto androgens are more potent than their 11β-hydroxy counterparts [76].”
From Human steroid biosynthesis, metabolism and excretion are differentially reflected by serum and urine steroid metabolomes: a comprehensive review (2019) · cites this paper as [76]
11KT and 11KDHT are full AR agonists with the same AR activating potential as T and DHT, respectively.
“While 11OHT and 11OHDHT represent partial AR agonists, 11KT and 11KDHT are full agonists with the same AR activating potential as T and DHT, respectively (Pretorius et al., 2016, Storbeck et al., 2013).”
From Intracrine androgen biosynthesis, metabolism and action revisited (2018) · cites this paper as Storbeck et al., 2013
The expression of HSD11B2 is required for the activation of 11OHA4, which is the primary 11-oxygenated C19 androgen precursor in circulation.
“It should also be noted that the expression of HSD11B2, which encodes the oxidative HSD11B isoform, is required for the activation of 11OHA4, which is the primary 11-oxygenated C19 androgen precursor in circulation (Rege et al., 2013, Storbeck et al., 2013, Swart et al., 2013) (Table 2).”
From Intracrine androgen biosynthesis, metabolism and action revisited (2018) · cites this paper as Storbeck et al., 2013
Prostate cancer cell lines are able to metabolise the adrenal androgen precursor 11OHA4.
“Recent studies have also shown that prostate cancer cell lines are able to metabolise the adrenal androgen precursor 11OHA4 (Storbeck et al., 2013, Swart et al., 2013, Swart and Storbeck, 2015).”
From Intracrine androgen biosynthesis, metabolism and action revisited (2018) · cites this paper as Storbeck et al., 2013
The 11-keto C19 steroids are more androgenic than their 11-hydroxy precursors.
“Significantly, it is the 11-keto C19 steroids that are more androgenic than their 11-hydroxy precursors (Storbeck et al., 2013)”
From Intracrine androgen biosynthesis, metabolism and action revisited (2018) · cites this paper as Storbeck et al., 2013
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“Furthermore, similar to the conversion of T to dihydrotestosterone (DHT) in target tissues, 11KT is a substrate for 5a-reductases (28).”
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Exploring the Predictive Role of 11‐Oxyandrogens in Diagnosing Polycystic Ovary Syndrome
Mody, A., Lodish, M. B., Auchus, R. J., Turcu, A. F., Jiang, F., & Huddleston, H. G. (2025) · Endocrinology Diabetes & Metabolism · doi:10.1002/edm2.70022 · Cited by 17 · see citing works
- Authors
- Storbeck, K.-H., Bloem, L. M., Africander, D., Schloms, L., Swart, P., & Swart, A. C.
- Affiliations
- Stellenbosch University (ZA)
- Corresponding author
- Swart, Amanda C.
- Venue
- Molecular and Cellular Endocrinology
- Publisher
- Elsevier BV
- Published
- 2013-09
- Volume
- 377
- Issue
- 1-2
- Pages
- 135-146
- ISSN
- 0303-7207 (ISSN-L)
- OpenAlex
- W2171708792
- Cited by
- 198
- References
- 58
- Citations by year
- 2026: 11 · 2025: 14 · 2024: 20 · 2023: 19 · 2022: 14 · 2021: 26 · 2020: 15 · 2019: 23 · 2018: 13 · 2017: 19 · 2016: 11 · 2015: 3 · 2014: 7 · 2013: 2
- FWCI
- 6.24
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Molecular and Cellular Endocrinology (publishedVersion)
- PubMed (publishedVersion)
- Funders
- National Research Foundation of South Africa (THRIP TP2011060100001)
- Topics
- Health Sciences › Medicine › Pulmonary and Respiratory Medicine › Prostate Cancer Treatment and Research
- Health Sciences › Medicine › Endocrinology, Diabetes and Metabolism › Hormonal and reproductive studies
- Health Sciences › Medicine › Endocrinology, Diabetes and Metabolism › Adrenal Hormones and Disorders
- Keywords
- C19 steroids, castration-resistant prostate cancer, adrenal steroid metabolism, androstenedione, dehydroepiandrosterone, androgen receptor transactivation, 5α-reduced steroids, androgen production
- MeSH terms
- Aldo-Keto Reductase Family 1 Member C3, Androgens, Androstenedione, Animals, Chromatography, High Pressure Liquid, Estradiol Dehydrogenases, Humans, Hydroxyprostaglandin Dehydrogenases, Hydroxytestosterones, Male, Membrane Proteins, Molecular Weight, Receptors, Androgen, Mass Spectrometry, Testosterone, 3-Oxo-5-alpha-Steroid 4-Dehydrogenase, Transfection, 3-Hydroxysteroid Dehydrogenases, Transcriptional Activation, 11-beta-Hydroxysteroid Dehydrogenase Type 1, Cell Line, Tumor, Biosynthetic Pathways, Prostatic Neoplasms, Castration-Resistant
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