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Chemical Compound Review

pregnenolone     1- [(3S,8S,9S,10R,13S,14S,17S)- 3-hydroxy-10...

Synonyms: Natolone, Prenolon, Enelone, Pregnetan, Pregneton, ...
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Disease relevance of pregnenolone


Psychiatry related information on pregnenolone


High impact information on pregnenolone


Chemical compound and disease context of pregnenolone


Biological context of pregnenolone

  • The results indicate that phosphorylation/dephosphorylation regulates pregnenolone-binding activity and influences the pattern of the PBP isoformation [20].
  • Double transfection with both P450scc and adrenodoxin plasmids leads to greater pregnenolone production and indicates that adrenodoxin plays a role as a substrate for this reaction or that bovine adrenodoxin serves as a better electron donor than the endogenous iron-sulfur protein renodoxin [21].
  • Pregnenolone 16 alpha-carbonitrile-inducible P-450 gene family: gene conversion and differential regulation [22].
  • The steady-state inhibition of the peak Ca2+ channel current evoked by depolarizing steps from -80 to -10 mV occurred in a concentration-dependent manner with the following IC50 values: pregnenolone sulfate (PES), 11 nM; pregnenolone (PE), 130 nM; and allotetrahydrocorticosterone (THCC), 298 nM [23].
  • 20 alpha-Hydroxycholesterol was found to be suitable providing correction was made for the one less hydroxylation required to convert this substrate into pregnenolone, compared to cholesterol [24].

Anatomical context of pregnenolone


Associations of pregnenolone with other chemical compounds


Gene context of pregnenolone

  • Interestingly, hPAR is not activated by pregnenolone 16alpha-carbonitrile, which is a potent inducer of murine CYP3A genes and an activator of the mouse receptor PXR [34].
  • In addition, the amino-terminal helix comprising residues Asp19 to Lys26, which determines the specificity difference between the SULT2B1 isoforms, becomes ordered upon pregnenolone binding, covering the substrate binding pocket [35].
  • Mitochondria isolated from cells treated with ODNs antisense, but not missense, to PBR failed to form pregnenolone and respond to either StAR or Tom/StAR proteins [36].
  • In addition, robust hepatic and intestinal induction with a range of reagents known to activate PXR and/or CAR (e.g., dexamethasone, pregnenolone 16alpha-carbonitrile, and phenobarbital) was observed [37].
  • Pregnenolone 16alpha-carbonitrile markedly induced hepatic CYP3A4 expression, and the level was higher in females than males [38].

Analytical, diagnostic and therapeutic context of pregnenolone


  1. Regulation of pregnenolone synthesis in C6-2B glioma cells by 4'-chlorodiazepam. Guarneri, P., Papadopoulos, V., Pan, B., Costa, E. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  2. Structure/function relationships responsible for coenzyme specificity and the isomerase activity of human type 1 3 beta-hydroxysteroid dehydrogenase/isomerase. Thomas, J.L., Duax, W.L., Addlagatta, A., Brandt, S., Fuller, R.R., Norris, W. J. Biol. Chem. (2003) [Pubmed]
  3. Pregnenolone, 17-OH-pregnenolone, and testosterone in plasma of patients with congenital adrenal hyperplasia. McKenna, T.J., Jennings, A.S., Liddle, G.W., Burr, I.M. J. Clin. Endocrinol. Metab. (1976) [Pubmed]
  4. Plasma pregnenolone and 17-OH-pregnenolone in patients with adrenal tumors, ACTH excess, or idiopathic hirsutism. McKenna, T.J., Miller, R.B., Liddle, G.W. J. Clin. Endocrinol. Metab. (1977) [Pubmed]
  5. Steroid enzyme activities in extraadrenal pheochromocytomas. Carballeira, A., Fishman, L.M. J. Clin. Endocrinol. Metab. (1982) [Pubmed]
  6. Individual differences in cognitive aging: implication of pregnenolone sulfate. Mayo, W., George, O., Darbra, S., Bouyer, J.J., Vallée, M., Darnaudéry, M., Pallarès, M., Lemaire-Mayo, V., Le Moal, M., Piazza, P.V., Abrous, N. Prog. Neurobiol. (2003) [Pubmed]
  7. Neuroactive steroids are altered in schizophrenia and bipolar disorder: relevance to pathophysiology and therapeutics. Marx, C.E., Stevens, R.D., Shampine, L.J., Uzunova, V., Trost, W.T., Butterfield, M.I., Massing, M.W., Hamer, R.M., Morrow, A.L., Lieberman, J.A. Neuropsychopharmacology (2006) [Pubmed]
  8. Low pregnenolone sulphate plasma concentrations in patients with generalized social phobia. Heydari, B., Le Mellédo, J.M. Psychological medicine. (2002) [Pubmed]
  9. The neurosteroid pregnenolone sulfate neutralized the learning impairment induced by intrahippocampal nicotine in alcohol-drinking rats. Martín-García, E., Pallarès, M. Neuroscience (2005) [Pubmed]
  10. An orphan nuclear receptor activated by pregnanes defines a novel steroid signaling pathway. Kliewer, S.A., Moore, J.T., Wade, L., Staudinger, J.L., Watson, M.A., Jones, S.A., McKee, D.D., Oliver, B.B., Willson, T.M., Zetterström, R.H., Perlmann, T., Lehmann, J.M. Cell (1998) [Pubmed]
  11. Sulfonation and molecular action. Strott, C.A. Endocr. Rev. (2002) [Pubmed]
  12. Progesterone synthesis and myelin formation by Schwann cells. Koenig, H.L., Schumacher, M., Ferzaz, B., Thi, A.N., Ressouches, A., Guennoun, R., Jung-Testas, I., Robel, P., Akwa, Y., Baulieu, E.E. Science (1995) [Pubmed]
  13. Reciprocal activation of xenobiotic response genes by nuclear receptors SXR/PXR and CAR. Xie, W., Barwick, J.L., Simon, C.M., Pierce, A.M., Safe, S., Blumberg, B., Guzelian, P.S., Evans, R.M. Genes Dev. (2000) [Pubmed]
  14. Endocrine glia: roles of glial cells in the brain actions of steroid and thyroid hormones and in the regulation of hormone secretion. Garcia-Segura, L.M., Chowen, J.A., Naftolin, F. Frontiers in neuroendocrinology. (1996) [Pubmed]
  15. Detection of P450c17-independent pathways for dehydroepiandrosterone (DHEA) biosynthesis in brain glial tumor cells. Cascio, C., Prasad, V.V., Lin, Y.Y., Lieberman, S., Papadopoulos, V. Proc. Natl. Acad. Sci. U.S.A. (1998) [Pubmed]
  16. Prenatal diagnosis of congenital lipoid adrenal hyperplasia. Saenger, P., Klonari, Z., Black, S.M., Compagnone, N., Mellon, S.H., Fleischer, A., Abrams, C.A., Shackelton, C.H., Miller, W.L. J. Clin. Endocrinol. Metab. (1995) [Pubmed]
  17. Modulation of the activity of human 17 alpha-hydroxylase-17,20-lyase (CYP17) by cytochrome b5: endocrinological and mechanistic implications. Lee-Robichaud, P., Wright, J.N., Akhtar, M.E., Akhtar, M. Biochem. J. (1995) [Pubmed]
  18. Acute effects of ethanol on steroidogenic acute regulatory protein (StAR) in the prepubertal rat ovary. Srivastava, V.K., Hiney, J.K., Dearth, R.K., Les Dees, W. Alcohol. Clin. Exp. Res. (2001) [Pubmed]
  19. Intrahippocampal nicotine and neurosteroids effects on the anxiety-like behaviour in voluntary and chronic alcohol-drinking rats. Martín-García, E., Pallarès, M. Behav. Brain Res. (2005) [Pubmed]
  20. Charge isoforms of the adrenocortical pregnenolone-binding protein: influence of phosphorylation on isoformation and binding activity. Lee, Y.C., Driscoll, W.J., Strott, C.A. Proc. Natl. Acad. Sci. U.S.A. (1990) [Pubmed]
  21. Simultaneous transfection of COS-1 cells with mitochondrial and microsomal steroid hydroxylases: incorporation of a steroidogenic pathway into nonsteroidogenic cells. Zuber, M.X., Mason, J.I., Simpson, E.R., Waterman, M.R. Proc. Natl. Acad. Sci. U.S.A. (1988) [Pubmed]
  22. Pregnenolone 16 alpha-carbonitrile-inducible P-450 gene family: gene conversion and differential regulation. Gonzalez, F.J., Song, B.J., Hardwick, J.P. Mol. Cell. Biol. (1986) [Pubmed]
  23. Neurosteroids modulate calcium currents in hippocampal CA1 neurons via a pertussis toxin-sensitive G-protein-coupled mechanism. ffrench-Mullen, J.M., Danks, P., Spence, K.T. J. Neurosci. (1994) [Pubmed]
  24. Comparison of pregnenolone synthesis by cytochrome P-450scc in mitochondria from porcine corpora lutea and granulosa cells of follicles. Tuckey, R.C., Holland, J.W. J. Biol. Chem. (1989) [Pubmed]
  25. Steroid production in the thymus: implications for thymocyte selection. Vacchio, M.S., Papadopoulos, V., Ashwell, J.D. J. Exp. Med. (1994) [Pubmed]
  26. Possible involvement of pregnane X receptor-enhanced CYP24 expression in drug-induced osteomalacia. Pascussi, J.M., Robert, A., Nguyen, M., Walrant-Debray, O., Garabedian, M., Martin, P., Pineau, T., Saric, J., Navarro, F., Maurel, P., Vilarem, M.J. J. Clin. Invest. (2005) [Pubmed]
  27. Hyperreninemic hypoaldosteronism after chronic stress in the rat. Aguilera, G., Kiss, A., Sunar-Akbasak, B. J. Clin. Invest. (1995) [Pubmed]
  28. Role of actin in the responses of adrenal cells to ACTH and cyclic AMP: inhibition by DNase I. Osawa, S., Betz, G., Hall, P.F. J. Cell Biol. (1984) [Pubmed]
  29. Endocrine regulation and communicating functions of the Leydig cell. Dufau, M.L. Annu. Rev. Physiol. (1988) [Pubmed]
  30. Cytochalasin-stimulated steroidogenesis from high density lipoproteins. Cortese, F., Wolf, J. J. Cell Biol. (1978) [Pubmed]
  31. Self-sufficient biosynthesis of pregnenolone and progesterone in engineered yeast. Duport, C., Spagnoli, R., Degryse, E., Pompon, D. Nat. Biotechnol. (1998) [Pubmed]
  32. Cyp7b, a novel brain cytochrome P450, catalyzes the synthesis of neurosteroids 7alpha-hydroxy dehydroepiandrosterone and 7alpha-hydroxy pregnenolone. Rose, K.A., Stapleton, G., Dott, K., Kieny, M.P., Best, R., Schwarz, M., Russell, D.W., Björkhem, I., Seckl, J., Lathe, R. Proc. Natl. Acad. Sci. U.S.A. (1997) [Pubmed]
  33. Neurosteroids: deficient cognitive performance in aged rats depends on low pregnenolone sulfate levels in the hippocampus. Vallée, M., Mayo, W., Darnaudéry, M., Corpéchot, C., Young, J., Koehl, M., Le Moal, M., Baulieu, E.E., Robel, P., Simon, H. Proc. Natl. Acad. Sci. U.S.A. (1997) [Pubmed]
  34. Identification of a human nuclear receptor defines a new signaling pathway for CYP3A induction. Bertilsson, G., Heidrich, J., Svensson, K., Asman, M., Jendeberg, L., Sydow-Bäckman, M., Ohlsson, R., Postlind, H., Blomquist, P., Berkenstam, A. Proc. Natl. Acad. Sci. U.S.A. (1998) [Pubmed]
  35. Crystal structure of human cholesterol sulfotransferase (SULT2B1b) in the presence of pregnenolone and 3'-phosphoadenosine 5'-phosphate. Rationale for specificity differences between prototypical SULT2A1 and the SULT2BG1 isoforms. Lee, K.A., Fuda, H., Lee, Y.C., Negishi, M., Strott, C.A., Pedersen, L.C. J. Biol. Chem. (2003) [Pubmed]
  36. Peripheral-type benzodiazepine receptor-mediated action of steroidogenic acute regulatory protein on cholesterol entry into leydig cell mitochondria. Hauet, T., Yao, Z.X., Bose, H.S., Wall, C.T., Han, Z., Li, W., Hales, D.B., Miller, W.L., Culty, M., Papadopoulos, V. Mol. Endocrinol. (2005) [Pubmed]
  37. Transgenic mouse models of human CYP3A4 gene regulation. Robertson, G.R., Field, J., Goodwin, B., Bierach, S., Tran, M., Lehnert, A., Liddle, C. Mol. Pharmacol. (2003) [Pubmed]
  38. Potential role for human cytochrome P450 3A4 in estradiol homeostasis. Yu, A.M., Fukamachi, K., Krausz, K.W., Cheung, C., Gonzalez, F.J. Endocrinology (2005) [Pubmed]
  39. Neurosteroids: pregnenolone in human sciatic nerves. Morfin, R., Young, J., Corpéchot, C., Egestad, B., Sjövall, J., Baulieu, E.E. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  40. Steroidogenic potential of lyophilized mitochondria from bovine adrenocortical tissue. Prasad, V.V., Mathur, C., Welch, M., Lieberman, S. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  41. Glucocorticoids and progestins signal the initiation and enhance the rate of myelin formation. Chan, J.R., Phillips, L.J., Glaser, M. Proc. Natl. Acad. Sci. U.S.A. (1998) [Pubmed]
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