Chemistry:5α-Pregnane-3α,11β-diol-20-one

From HandWiki

5α-Pregnane-3α,11β-diol-20-one, abbreviated as 3,11diOH-DHP4,[1] also known as 3α,11β-dihydroxy-5α-pregnan-20-one, is an endogenous steroid.[2][3][4]

The steroid 5α-pregnan-3α,11β-diol-20-one (3,11diOH-DHP4) plays a role in the 11-oxygenated steroid backdoor pathway to androgens as a metabolic intermediate. This pathway involves the metabolism of C21 steroids (pregnanes) via enzymes such as steroid 11β-hydroxylase (CYP11B1), steroid 5α-reductase (SRD5A1), 17α-hydroxylase/17,20-lyase (CYP17A1), resulting in the production of androgen precursors.[5][1] Docking studies have shown that the C11-oxy group of 3,11diOH-DHP4 and alfaxalone does not significantly affect their binding to CYP17A1. Furthermore, it has been observed that the lyase activity of CYP17A1 is impaired by the C11-hydroxyl (-OH) and keto- (=O) moieties present in these steroids. The lyase activity of CYP17A1 converts intermediates like 3,11diOH-DHP4 to potent androgens such as 5α-pregnan-3α,11β,17α-triol-20-one (11OH-Pdiol). These findings indicate that CYP17A1 plays a role in the metabolism of this steroid through both hydroxylation and lyase reactions in the 11-oxygenated steroid backdoor pathway to androgens.[1][6] This pathway is important for regulating adrenal and gonadal steroid hormone biosynthesis and can contribute to elevated levels of androgens in certain conditions.[1][5][6]

References

  1. ↑ 1.0 1.1 1.2 1.3 "CYP17A1 exhibits 17αhydroxylase/17,20-lyase activity towards 11β-hydroxyprogesterone and 11-ketoprogesterone metabolites in the C11-oxy backdoor pathway". J Steroid Biochem Mol Biol 199. May 2020. doi:10.1016/j.jsbmb.2020.105614. PMID 32007561. 
  2. ↑ "Identification of neuroactive steroids and their precursors and metabolites in adult male rat brain". Endocrinology 147 (1): 179–90. January 2006. doi:10.1210/en.2005-1065. PMID 16223859. http://discovery.ucl.ac.uk/191787/7/Fry_Endocrinology29Sep05TMP-05-02021_11.pdf. 
  3. ↑ "Self-augmentation effect of male-specific products on sexually differentiated progesterone metabolism in adult male rat liver microsomes". J Biol Chem 276 (7): 4604–10. February 2001. doi:10.1074/jbc.M003355200. PMID 10995741. 
  4. ↑ "Studies on 16α-Hydroxylation of Steroid Molecules and Regioselective Binding Mode in Homology-Modeled Cytochrome P450-2C11". Int J Med Chem 2011. 2011. doi:10.1155/2011/918168. PMID 27516905. 
  5. ↑ 5.0 5.1 "Alternative androgen pathways". WikiJournal of Medicine 10: 29. 3 April 2023. doi:10.15347/WJM/2023.003. https://upload.wikimedia.org/wikiversity/en/a/a7/Alternative_androgens_pathways.pdf.  This article incorporates text from this source, which is available under the CC BY 4.0 license.
  6. ↑ 6.0 6.1 "Allopregnanolone and pregnanolone analogues modified in the C ring: synthesis and activity". J Med Chem 56 (6): 2323–36. March 2013. doi:10.1021/jm3016365. PMID 23421641. 



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