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17α-Hydroxypregnenolone

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17α-Hydroxypregnenolone
Pharmacokinetic data
MetabolismAdrenal, Gonads
Identifiers
  • 3β,17-dihydroxypregn-5-en-20-one
CAS Number
PubChem CID
ChemSpider
ChEBI
CompTox Dashboard (EPA)
ECHA InfoCard100.006.239 Edit this at Wikidata
Chemical and physical data
FormulaC21H32O3
Molar mass332.48 g/mol g·mol−1
3D model (JSmol)
Melting point268 °C (514 °F)
  • CC[C@@]2(O)CC[C@H]1[C@@H]3CCC4CC(O)C(=O)C[C@]4(C)[C@H]3CC[C@@]12C
  • InChI=1S/C21H34O3/c1-4-21(24)10-8-16-14-6-5-13-11-17(22)18(23)12-19(13,2)15(14)7-9-20(16,21)3/h13-17,22,24H,4-12H2,1-3H3/t13?,14-,15+,16+,17?,19+,20+,21-/m1/s1 checkY
  • Key:QPLFSAZMHUAMKE-FOCOMJRBSA-N checkY
  (verify)

17-Hydroxypregnenolone (also 17-OH-pregnenolone and 17α-hydroxypregnenolone), is a C21 steroid that is obtained by hydroxylation of pregnenolone at the C17α position. This step is performed by the mitochondrial cytochrome P450 enzyme 17α-hydroxylase (CYP17A1) that is present in the adrenal and gonads. Peak levels are reached in humans at the end of puberty and then decline.[1] High levels are also achieved during pregnancy.

Prohormone

17 OH–pregnenolone is converted from pregnenolone and gives rise to DHEA (below) and to 17 OH-progesterone (to its right)

17-OH-pregnenolone is considered a prohormone in the formation of dehydroepiandrosterone (DHEA), itself a prohormone of the sex steroids.

This conversion is mediated by the enzyme 17,20 lyase. As such 17-OH-pregenolone represents an intermediary in the delta-5-pathway that leads from pregnenolone to DHEA. 17-hydroxypregneolone is also converted to 17-hydroxyprogesterone, a prohormone for glucocorticosteroids and androstenedione through the activity of 3-hydroxysteroid dehydrogenase.

Neurohormone

There is some evidence that 17-OH-pregnenolone may have activity as a neurohormone.[2]

Clinical use

Measurements of 17-OH-pregnenolone are useful in the diagnosis of certain forms of congenital adrenal hyperplasia.[3] In patients with congenital adrenal hyperplasia due to 3 beta-hydroxysteroid dehydrogenase deficiency 17-OH-pregnenolone is increased, while in patients with congenital adrenal hyperplasia due to 17 alpha-hydroxylase deficiency levels are low to absent.

See also

Congenital adrenal hyperplasia

Additional images

References

  1. ^ Hill, M; Lukác, D; Lapcík, O; Sulcová, J; Hampl, R; Pouzar, V; Stárka, L (1999). "Age relationships and sex differences in serum levels of pregnenolone and 17-hydroxypregnenolone in healthy subjects". Clinical chemistry and laboratory medicine : CCLM / FESCC. 37 (4): 439–47. doi:10.1515/CCLM.1999.072. PMID 10369116.
  2. ^ Matsunaga, M; Ukena, K; Baulieu, EE; Tsutsui, K (2004). "7α-Hydroxypregnenolone acts as a neuronal activator to stimulate locomotor activity of breeding newts by means of the dopaminergic system". Proceedings of the National Academy of Sciences of the United States of America. 101 (49): 17282–7. doi:10.1073/pnas.0407176101. PMC 535386. PMID 15569930.
  3. ^ Riepe FG, Mahler P, Sippell, Partsch CJ. Longitudinal Study of Plasma Pregnenolone and 17-Hydroxypregnenolone in Full-Term and Preterm Neonates at Birth and during the Early Neonatal Period. The Journal of Clinical Endocrinology & Metabolism (2002) 87: 4301-4306 [1]


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