5α-Pregnane-3α,17α-diol-20-one explained

5α-Pregnane-3α,17α-diol-20-one, also known as 17α-hydroxyallopregnanolone (17-OH-allo) is an endogenous steroid.

Function

5α-Pregnane-3α,17α-diol-20-one is a metabolite, an intermediate product within the androgen backdoor pathway[1] in which 17α-hydroxyprogesterone (17-OHP) is 5α-reduced and finally converted to 5α-dihydrotestosterone (DHT) without testosterone as a metabolic intermediate.[2] [3]

The pathway can be outlined as 17-OHP → 5α-pregnan-17α-ol-3,20-dione → 5α-pregnane-3α,17α-diol-20-one → androsterone → 5α-androstane-3α,17β-diol → DHT.[4] [5] [6]

Biosynthesis

5α-Pregnane-3α,17α-diol-20-one is produced from 5α-pregnan-17α-ol-3,20-dione[7] in a reaction catalyzed by a reductive 3α-hydroxysteroid dehydrogenase (3α-HSD),[8] i.e. by the two aldo-keto reductase isozymes: AKR1C2 and AKR1C4, and by 17β-hydroxysteroid dehydrogenase 6 (HSD17B6) that also has the 3α-HSD activity.[9]

See also

Notes and References

  1. 10.15347/WJM/2023.003 . free. Alternative androgen pathways . 2023 . Masiutin M, Yadav M . WikiJournal of Medicine . 10 . X . 257943362.
  2. Auchus RJ . The backdoor pathway to dihydrotestosterone . Trends in Endocrinology and Metabolism . 15 . 9 . 432–438 . November 2004 . 15519890 . 10.1016/j.tem.2004.09.004 . 10631647 .
  3. Kamrath C, Hochberg Z, Hartmann MF, Remer T, Wudy SA . Increased activation of the alternative "backdoor" pathway in patients with 21-hydroxylase deficiency: evidence from urinary steroid hormone analysis . The Journal of Clinical Endocrinology and Metabolism . 97 . 3 . E367–E375 . March 2012 . 22170725 . 10.1210/jc.2011-1997 . free .
  4. O'Shaughnessy PJ, Antignac JP, Le Bizec B, Morvan ML, Svechnikov K, Söder O, Savchuk I, Monteiro A, Soffientini U, Johnston ZC, Bellingham M, Hough D, Walker N, Filis P, Fowler PA . 6 . Alternative (backdoor) androgen production and masculinization in the human fetus . PLOS Biology . 17 . 2 . e3000002 . February 2019 . 30763313 . 6375548 . 10.1371/journal.pbio.3000002 . free .
  5. Fukami M, Homma K, Hasegawa T, Ogata T . Backdoor pathway for dihydrotestosterone biosynthesis: implications for normal and abnormal human sex development . Developmental Dynamics . 242 . 4 . 320–329 . April 2013 . 23073980 . 10.1002/dvdy.23892 . 44702659 . free .
  6. Miller WL, Auchus RJ . The "backdoor pathway" of androgen synthesis in human male sexual development . PLOS Biology . 17 . 4 . e3000198 . April 2019 . 30943210 . 6464227 . 10.1371/journal.pbio.3000198 . free .
  7. Baronio F, Ortolano R, Menabò S, Cassio A, Baldazzi L, Di Natale V, Tonti G, Vestrucci B, Balsamo A . 6 . 46,XX DSD due to Androgen Excess in Monogenic Disorders of Steroidogenesis: Genetic, Biochemical, and Clinical Features . International Journal of Molecular Sciences . 20 . 18 . 4605 . September 2019 . 31533357 . 6769793 . 10.3390/ijms20184605 . free .
  8. Sharifi N, McPhaul MJ, Auchus RJ . "Getting from here to there"--mechanisms and limitations to the activation of the androgen receptor in castration-resistant prostate cancer . Journal of Investigative Medicine . 58 . 8 . 938–944 . December 2010 . 21030877 . 5589138 . 10.2310/JIM.0b013e3181ff6bb8 . The product of 17-hydroxyprogesterone reduction, 5α-pregnan-17α-ol-3,20-dione, was metabolized by a reductive 3α-HSD to a new key intermediate, 5α-pregnane-3α,17α-diol-20-one (Pdiol) .
  9. Miller WL . The syndrome of 17,20 lyase deficiency . The Journal of Clinical Endocrinology and Metabolism . 97 . 1 . 59–67 . January 2012 . 22072737 . 3251937 . 10.1210/jc.2011-2161 .

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