5α-Pregnane-3α,11β-diol-20-one

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5α-Pregnane-3α,11β-diol-20-one
Identifiers
3D model (JSmol)
  • CC(=O)C1CCC2C1(CC(C3C2CCC4C3(CCC(C4)O)C)O)C
Properties
C21H34O3
Molar mass 334.500 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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[edit]

  1. ^ a b c d van Rooyen D, Yadav R, Scott EE, Swart AC (May 2020). "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: 105614. doi:10.1016/j.jsbmb.2020.105614. PMID 32007561. S2CID 210955834.
  2. ^ Ebner MJ, Corol DI, Havlíková H, Honour JW, Fry JP (January 2006). "Identification of neuroactive steroids and their precursors and metabolites in adult male rat brain" (PDF). Endocrinology. 147 (1): 179–90. doi:10.1210/en.2005-1065. PMID 16223859.
  3. ^ Yamada A, Yamada M, Fujita Y, Nishigami T, Nakasho K, Uematsu K (February 2001). "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. doi:10.1074/jbc.M003355200. PMID 10995741.
  4. ^ Ali HI, Yamada M, Fujita Y, Maeda M, Akaho E (2011). "Studies on 16α-Hydroxylation of Steroid Molecules and Regioselective Binding Mode in Homology-Modeled Cytochrome P450-2C11". Int J Med Chem. 2011: 918168. doi:10.1155/2011/918168. PMC 4970648. PMID 27516905.
  5. ^ a b Masiutin MM, Yadav MK (3 April 2023). "Alternative androgen pathways" (PDF). WikiJournal of Medicine. 10: 29. doi:10.15347/WJM/2023.003. S2CID 257943362. This article incorporates text from this source, which is available under the CC BY 4.0 license.
  6. ^ a b Slavíková B, Bujons J, Matyáš L, Vidal M, Babot Z, Krištofíková Z, Suñol C, Kasal A (March 2013). "Allopregnanolone and pregnanolone analogues modified in the C ring: synthesis and activity". J Med Chem. 56 (6): 2323–36. doi:10.1021/jm3016365. hdl:10261/89237. PMID 23421641.
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