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{{Short description|Chemical compound}}
{{Drugbox
{{Drugbox
| Verifiedfields = changed
| Verifiedfields = changed
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| IUPAC_name = 3β,17α-dihydroxypregn-5-en-20-one
| IUPAC_name = 3β,17α-dihydroxypregn-5-en-20-one
| image = 17-Hydroxypregnenolone.svg
| image = 17-Hydroxypregnenolone.svg
| width = 250
| image2 = 17-Hidroxipregnenolona3D.png
| image2 = 17-Hidroxipregnenolona3D.png
| width2 = 250
<!--Clinical data-->
<!--Clinical data-->
| tradename =
| tradename =
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| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 387-79-1
| CAS_number = 387-79-1
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 77ME40334S
| ATC_prefix =
| ATC_prefix =
| ATC_suffix =
| ATC_suffix =
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| C=21 | H=32
| C=21 | H=32
| O=3
| O=3
| molecular_weight = 332.48 g/mol
| smiles = CC[C@@]2(O)CC[C@H]1[C@@H]3CCC4CC(O)C(=O)C[C@]4(C)[C@H]3CC[C@@]12C
| smiles = CC[C@@]2(O)CC[C@H]1[C@@H]3CCC4CC(O)C(=O)C[C@]4(C)[C@H]3CC[C@@]12C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
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}}
}}


'''17α-Hydroxypregnenolone''' is a [[pregnane]] (C21) [[steroid]] that is obtained by [[hydroxylation]] of [[pregnenolone]] at the C17α position. This step is performed by the [[mitochondria]]l [[cytochrome P450 oxidase|cytochrome P450 enzyme]] 17α-hydroxylase ([[CYP17A1]]) that is present in the [[adrenal]] and [[gonad]]s. Peak levels are reached in humans at the end of [[puberty]] and then decline.<ref>{{cite journal | last1 = Hill | first1 = M | last2 = Lukác | first2 = D | last3 = Lapcík | first3 = O | last4 = Sulcová | first4 = J | last5 = Hampl | first5 = R | last6 = Pouzar | first6 = V | last7 = Stárka | first7 = L | title = Age relationships and sex differences in serum levels of pregnenolone and 17-hydroxypregnenolone in healthy subjects | journal = [[Clinical chemistry and laboratory medicine]] : CCLM / FESCC | volume = 37 | issue = 4 | pages = 439–47 | year = 1999 | pmid = 10369116 | doi = 10.1515/CCLM.1999.072 }}</ref> High levels are also achieved during [[pregnancy]].
'''17α-Hydroxypregnenolone''' is a [[pregnane]] (C21) [[steroid]] that is obtained by [[hydroxylation]] of [[pregnenolone]] at the C17α position. This step is performed by the [[mitochondria]]l [[cytochrome P450 oxidase|cytochrome P450 enzyme]] 17α-hydroxylase ([[CYP17A1]]) that is present in the [[adrenal]] and [[gonad]]s. Peak levels are reached in humans at the end of [[puberty]] and then decline.<ref>{{cite journal | vauthors = Hill M, Lukác D, Lapcík O, Sulcová J, Hampl R, Pouzar V, Stárka L | title = Age relationships and sex differences in serum levels of pregnenolone and 17-hydroxypregnenolone in healthy subjects | journal = Clinical Chemistry and Laboratory Medicine | volume = 37 | issue = 4 | pages = 439–47 | date = April 1999 | pmid = 10369116 | doi = 10.1515/CCLM.1999.072 | s2cid = 41315909 }}</ref> High levels are also achieved during [[pregnancy]]. It is also a known [[Neuromodulation|neuromodulator]].


==Prohormone==
==Prohormone==
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==Clinical use==
==Clinical use==
Measurements of 17α-hydroxypregnenolone are useful in the diagnosis of certain forms of [[congenital adrenal hyperplasia]].<ref>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
Measurements of 17α-hydroxypregnenolone are useful in the diagnosis of certain forms of [[congenital adrenal hyperplasia]].<ref>{{cite journal | vauthors = Riepe FG, Mahler P, Sippell WG, Partsch CJ | title = Longitudinal study of plasma pregnenolone and 17-hydroxypregnenolone in full-term and preterm neonates at birth and during the early neonatal period | journal = The Journal of Clinical Endocrinology and Metabolism | volume = 87 | issue = 9 | pages = 4301–6 | date = September 2002 | pmid = 12213889 | doi = 10.1210/jc.2002-020452 | doi-access = free }}</ref>
[http://jcem.endojournals.org/cgi/content/full/87/9/4301]</ref>
In patients with [[congenital adrenal hyperplasia due to 3β-hydroxysteroid dehydrogenase deficiency]] 17α-hydroxypregnenolone is increased, while in patients with [[congenital adrenal hyperplasia due to 17α-hydroxylase deficiency]] levels are low to absent.
In patients with [[congenital adrenal hyperplasia due to 3β-hydroxysteroid dehydrogenase deficiency]] 17α-hydroxypregnenolone is increased, while in patients with [[congenital adrenal hyperplasia due to 17α-hydroxylase deficiency]] levels are low to absent.


==See also==
== Neurosteroid ==
17α-hydroxypregnenolone is a known neuromodulator as its acts in the [[central nervous system]]. Specifically, it is known to modulate [[Animal locomotion|locomotion]].<ref>{{cite journal | vauthors = Tsutsui K, Haraguchi S, Vaudry H | title = 7α-Hydroxypregnenolone regulating locomotor behavior identified in the brain and pineal gland across vertebrates | journal = General and Comparative Endocrinology | volume = 265 | pages = 97–105 | date = September 2018 | pmid = 28919448 | doi = 10.1016/j.ygcen.2017.09.014 | s2cid = 5636071 }}</ref>

== See also ==
* [[Congenital adrenal hyperplasia]]
* [[Congenital adrenal hyperplasia]]
* [[Narave pig]], intersex pigs that have low levels of 17α-Hydroxypregnenolone


==Additional images==
==Additional images==
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</gallery>
</gallery>


==References==
== References ==
{{Reflist|2}}
{{Reflist}}



{{Endogenous steroids}}
{{Endogenous steroids}}
{{Nuclear receptor modulators}}
{{Xenobiotic-sensing receptor modulators}}


{{DEFAULTSORT:Hydroxypregnenolone, 17α-}}
{{DEFAULTSORT:Hydroxypregnenolone, 17α-}}

Latest revision as of 19:10, 8 March 2023

17α-Hydroxypregnenolone
Pharmacokinetic data
MetabolismAdrenal, Gonads
Identifiers
  • 3β,17α-dihydroxypregn-5-en-20-one
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
CompTox Dashboard (EPA)
ECHA InfoCard100.006.239 Edit 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 a pregnane (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. It is also a known neuromodulator.

Prohormone

[edit]

17α-Hydroxypregnenolone 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 17α-hydroxypregenolone represents an intermediary in the Δ5 pathway that leads from pregnenolone to DHEA. 17α-Hydroxypregneolone is also converted to 17α-hydroxyprogesterone, a prohormone for glucocorticosteroids and androstenedione through the activity of 3α-hydroxysteroid dehydrogenase.

Clinical use

[edit]

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

Neurosteroid

[edit]

17α-hydroxypregnenolone is a known neuromodulator as its acts in the central nervous system. Specifically, it is known to modulate locomotion.[3]

See also

[edit]

Additional images

[edit]

References

[edit]
  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.
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