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Chemical Compound Review:

androsterone (3R,5S,8R,9S,10S,13S,14S)-3- hydroxy-10,13...

Synonyms: Androtin, Androtine, Androkinin, Androkinine, UPCMLD-DP124, ...

Mishler, J.M. et al., Chai, X. et al., Beaulieu, M. et al., Ge, R.S. et al., Bélanger, A. et al., et al.

Bélanger, Pelletier, Labrie, Barbier, Chouinard,

Welcome! If you are familiar with the subject of this article, you can contribute to this open access knowledge base by deleting incorrect information, restructuring or completely rewriting any text. Read more.

Disease relevance of androsterone

Urinary aetiocholanolone in patients with early breast cancer from South East Scotland and South Wales [1].
LNCaP, a human prostate cancer cell line, metabolizes testosterone into a variety of 5 alpha-reduced C19 steroids, such as dihydrotestosterone (DHT), androstane-3 alpha, 17 beta-diol (3 beta, 17 beta-DIOL), and androsterone (ADT) [2].
5. These observations suggest the involvement of the 17-oxosteroids, espically aetiocholanolone, in the pathogenesis of hereditary coproporphyria [3].

High impact information on androsterone

It is postulated that the conjugating activity of UGT enzymes is the main mechanism for modulating the action of steroids and protecting the androgen-sensitive tissues from deleteriously high concentrations of DHT, ADT and 3alpha-DIOL [4].
The predominant androgen produced by progenitor, immature, and adult Leydig cells differed, with AO being released by progenitor cells (72.08 +/- 9.02% of total androgens), 3alpha-DIOL by immature Leydig cells (73.33 +/- 14.52%), and T by adult Leydig cells (74.38 +/- 14.73%) [5].
Mouse rdh6 encodes cis-retinoid/androgen dehydrogenase type 1 (CRAD1), a short-chain dehydrogenase, which recognizes as substrates 9-cis-retinol, 11-cis-retinol, 5 alpha-androstan-3 alpha,17 beta-diol and 5 alpha-androstan-3 alpha-ol-17-one, and is expressed most intensely in liver and kidney [6].
Sertoli cells from immature rats metabolized (3H) 5 alpha-androstane-3 alpha, 17 beta-diol to (3H) 5 alpha-androstane-3 alpha, 16 alpha, 17 beta-triol and (3H) 3 alpha-hydroxy-5 alpha-androstan-17-one [7].
UGT2B17 is a UDP-glucuronosyltransferase enzyme expressed in several extrahepatic steroid target tissues, including the human prostate, where it glucuronidates C19 steroids such as dihydrotestosterone (DHT), androsterone (ADT), and androstane-3alpha, 17beta-diol (3alpha-diol) [8].

Biological context of androsterone

No correlation was found between the aetiocholanolone patterns and the basal body temperature [9].

Anatomical context of androsterone

Alkaline phosphatase as a marker of maturity in human neutrophils. Studies in normals dosed with aetiocholanolone and prednisolone [10].

Associations of androsterone with other chemical compounds

Urinary aetiocholanolone, androsterone and C19 and C21 5 beta/5 alpha metabolite ratios were analyzed by capillary gas chromatography [11].
Changes in the level of neutrophil alkaline phosphatase (NAP) in a population of peripheral blood neutrophils were determined in healthy subjects dosed with either aetiocholanolone (Aetio, 4 mg/m2 im) or prednisolone sodium succinate (Pred, 30 mg/m2 iv) [10].
We found that UGT2B17 is expressed in basal cells where DHEA is converted into 3alpha-DIOL and ADT [12].

References

Urinary aetiocholanolone in patients with early breast cancer from South East Scotland and South Wales. Miller, W.R., Hamilton, T., Champion, H.R., Wallace, I.W., Forrest, A.P., Prescott, R.J., Cameron, E.H., Griffiths, K. Br. J. Cancer (1975) [Pubmed]
Glucuronosyltransferase activity in human cancer cell line LNCaP. Guillemette, C., Bélanger, A. Mol. Cell. Endocrinol. (1995) [Pubmed]
Urinary excretion of 17-oxosteroids in hereditary coproporphyria. Paxton, J.W., Moore, M.R., Beattie, A.D., Goldberg, A. Clinical science and molecular medicine. (1975) [Pubmed]
Inactivation of androgens by UDP-glucuronosyltransferase enzymes in humans. Bélanger, A., Pelletier, G., Labrie, F., Barbier, O., Chouinard, S. Trends Endocrinol. Metab. (2003) [Pubmed]
Variation in the end products of androgen biosynthesis and metabolism during postnatal differentiation of rat Leydig cells. Ge, R.S., Hardy, M.P. Endocrinology (1998) [Pubmed]
Structure, promoter and chromosomal localization of rdh6. Chai, X., Chen, W., Napoli, J.L. Gene (2001) [Pubmed]
Metabolism of (3H) 5 alpha-androstane-3 alpha, 17 beta-diol by cultures of isolated rat sertoli cells and the effect of LH and FSH. Tcholakian, R.K., Berkowitz, A.S., Newaz, S.N. Steroids (1984) [Pubmed]
Chromosomal localization, structure, and regulation of the UGT2B17 gene, encoding a C19 steroid metabolizing enzyme. Beaulieu, M., Lévesque, E., Tchernof, A., Beatty, B.G., Bélanger, A., Hum, D.W. DNA Cell Biol. (1997) [Pubmed]
Serum levels of unconjugated aetiocholanolone androstenedione, testosterone, dehydroepiandrosterone, aldosterone, progesterone and oestrogens during the normal menstrual cycle. Frölich, M., Brand, E.C., van Hall, E.V. Acta Endocrinol. (1976) [Pubmed]
Alkaline phosphatase as a marker of maturity in human neutrophils. Studies in normals dosed with aetiocholanolone and prednisolone. Mishler, J.M., Williams, D.M. J. Clin. Pathol. (1980) [Pubmed]
Male pseudohermaphroditism due to primary 5 alpha-reductase deficiency: variation in gender identity reversal in seven Mexican patients from five different pedigrees. Méndez, J.P., Ulloa-Aguirre, A., Imperato-McGinley, J., Brugmann, A., Delfin, M., Chávez, B., Shackleton, C., Kofman-Alfaro, S., Pérez-Palacios, G. J. Endocrinol. Invest. (1995) [Pubmed]
Cellular specific expression of the androgen-conjugating enzymes UGT2B15 and UGT2B17 in the human prostate epithelium. Chouinard, S., Pelletier, G., Bélanger, A., Barbier, O. Endocr. Res. (2004) [Pubmed]

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