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17α-Hydroxypregnenolone

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
17α-Hydroxypregnenolone
Pharmacokinetic data
MetabolismAdrenal,Gonads
Identifiers
  • 3β,17α-dihydroxypregn-5-en-20-one
CAS Number
PubChemCID
ChemSpider
UNII
ChEBI
CompTox Dashboard(EPA)
ECHA InfoCard100.006.239Edit this at Wikidata
Chemical and physical data
FormulaC21H32O3
Molar mass332.484 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
 ☒NcheckY (what is this?)  (verify)

17α-Hydroxypregnenolone is apregnane (C21)steroid that is obtained byhydroxylation ofpregnenolone at the C17α position. This step is performed by themitochondrialcytochrome P450 enzyme 17α-hydroxylase (CYP17A1) that is present in theadrenal andgonads. Peak levels are reached in humans at the end ofpuberty and then decline.[1] High levels are also achieved duringpregnancy. It is also a knownneuromodulator.

Prohormone

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17α-Hydroxypregnenolone is considered aprohormone in the formation ofdehydroepiandrosterone (DHEA), itself a prohormone of thesex steroids.

This conversion is mediated by the enzyme 17,20 lyase. As such 17α-hydroxypregnenolone represents an intermediary in the Δ5 pathway that leads from pregnenolone to DHEA. 17α-Hydroxypregnenolone is also converted to17α-hydroxyprogesterone, a prohormone forglucocorticosteroids andandrostenedione through the activity of3α-hydroxysteroid dehydrogenase.

Clinical use

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Measurements of 17α-hydroxypregnenolone are useful in the diagnosis of certain forms ofcongenital adrenal hyperplasia.[2]In patients withcongenital adrenal hyperplasia due to 3β-hydroxysteroid dehydrogenase deficiency 17α-hydroxypregnenolone is increased, while in patients withcongenital adrenal hyperplasia due to 17α-hydroxylase deficiency levels are low to absent.

Neurosteroid

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17α-hydroxypregnenolone is a known neuromodulator as its acts in thecentral nervous system. Specifically, it is known to modulatelocomotion.[3]

See also

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Additional images

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References

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  1. ^Hill M, Lukác D, Lapcík O, Sulcová J, Hampl R, Pouzar V, Stárka L (April 1999). "Age relationships and sex differences in serum levels of pregnenolone and 17-hydroxypregnenolone in healthy subjects".Clinical Chemistry and Laboratory Medicine.37 (4):439–47.doi:10.1515/CCLM.1999.072.PMID 10369116.S2CID 41315909.
  2. ^Riepe FG, Mahler P, Sippell WG, Partsch CJ (September 2002)."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 and Metabolism.87 (9):4301–6.doi:10.1210/jc.2002-020452.PMID 12213889.
  3. ^Tsutsui K, Haraguchi S, Vaudry H (September 2018). "7α-Hydroxypregnenolone regulating locomotor behavior identified in the brain and pineal gland across vertebrates".General and Comparative Endocrinology.265:97–105.doi:10.1016/j.ygcen.2017.09.014.PMID 28919448.S2CID 5636071.
Precursors
Corticosteroids
Glucocorticoids
Mineralocorticoids
Sex steroids
Androgens
Estrogens
Progestogens
Neurosteroids
Others
CARTooltip Constitutive androstane receptor
PXRTooltip Pregnane X receptor
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