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{{Short description|Chemical compound}}
{| border="1" cellpadding="2" cellspacing="0" width="250px" align="right" style="border-collapse:collapse;"
{{Drugbox
|-
| Verifiedfields = changed
|bgcolor="#ffffff" align="center" colspan=2|Chemical structure of 17-hydroxypregnenolone]]<br><small>17-alpha hydroxypregnenolone</small>
| verifiedrevid = 477209164
|-
| IUPAC_name = 3β,17α-dihydroxypregn-5-en-20-one
|align="center" colspan=2 |<font size="-1">'' pregn-5-en-20-one, 3,17-dihydroxy-, (3beta)-''</font>
| image = 17-Hydroxypregnenolone.svg
|- align="center" style="border-bottom: 3px solid gray"
| width = 250
| '''[[CAS number]]''' <br/> [387-79-1]
| image2 = 17-Hidroxipregnenolona3D.png
|-
| width2 = 250
|bgcolor="#efefef"|Empirical formula
<!--Clinical data-->
|bgcolor="#dfefff"|C<sub>21</sub>H<sub>32</sub>O<sub>3</sub>
| tradename =
|-
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
|bgcolor="#efefef"|[[Molecular weight]]
| pregnancy_US = <!-- A / B / C / D / X -->
|bgcolor="#dfefff"|332.48
| pregnancy_category =
|-
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S8 -->
|bgcolor="#efefef"|Bioavailability
| legal_UK = <!-- GSL / P / POM / CD -->
|bgcolor="#dfefff"|
| legal_US = <!-- OTC / Rx-only -->
|-
| legal_status =
|bgcolor="#efefef"|Metabolism
| routes_of_administration =
|bgcolor="#dfefff"|[[Adrenal]][[Gonad]]s
<!--Pharmacokinetic data-->
|-
| bioavailability =
|bgcolor="#efefef"|[[half life|Elimination half life]]
| protein_bound =
|bgcolor="#dfefff"|
| metabolism = [[Adrenal]], [[Gonad]]s
|-
| elimination_half-life =
|bgcolor="#efefef"|[[Excretion]]
| excretion =
|bgcolor="#dfefff"|
<!--Identifiers-->
|-
| CAS_number_Ref = {{cascite|correct|??}}
|bgcolor="#efefef"|[[Pregnancy category (pharmaceutical) | Pregnancy category]]
| CAS_number = 387-79-1
|bgcolor="#dfefff"|
| UNII_Ref = {{fdacite|correct|FDA}}
|-
| UNII = 77ME40334S
| align="center" colspan=2 | '''Physical properties'''
| ATC_prefix =
|-
| ATC_suffix =
|bgcolor="#efefef"|[[Melting point]]
| PubChem = 3032570
|bgcolor="#dfefff"|268&deg;C
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
|-
| DrugBank =
|}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 17215939
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 28750
<!--Chemical data-->
| C=21 | H=32
| O=3
| 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 = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = QPLFSAZMHUAMKE-FOCOMJRBSA-N
| melting_point = 268
}}


'''17-Hydroxypregnenolone''', also '''17-OH-pregnenolone''' and more precisely '''17α-hydroxypregnenolone''', is a C21 [[steroid]] that is obtained by [[hydroxylation]] of [[pregnenolone]] at the C 17 alpha-position. This step is performed by the [[mitochondria]]l [[enzyme]] [[17α-hydroxylase]] that is present in the [[adrenal]] and [[gonad]]s. Peak levels are reached in humans at the end of [[puberty]] and then decline.<ref>Hill M, Lukac D, Lapcik O, Sulcova J, Hampl R, Pouzar V, Starka L. Age relationships and sex differences in serum levels of pregnenolone and 17-hydroxypregnenolone in healthy subjects. Clin Chem Lab Med. 1999 Apr;37(4):439-47. PMID 10369116</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==
17-OH-pregnenolone is considered a [[prohormone]] in the formation of [[dehydroepiandrosterone]] (DHEA), itself a prohomone of the sex steroids. [[Image:DHEA1.png|thumb|left|350px|17&alpha OH–pregnenolone is converted from pregnenolone and gives rise to DHEA; left side of reaction scheme]]
17α-Hydroxypregnenolone is considered a [[prohormone]] in the formation of [[dehydroepiandrosterone]] (DHEA), itself a prohormone of the [[sex steroid]]s.
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 be converted to [[17-hydroxyprogesterone]], a prohomone for the [[glucocorticosteroid]]s and [[androstenedione]], through the activity of 3-hydroxysteroid dehydrogenase.


This conversion is mediated by the enzyme 17,20 lyase. As such 17α-hydroxypregenolone represents an intermediary in the Δ<sup>5</sup> pathway that leads from pregnenolone to DHEA. 17α-Hydroxypregneolone is also converted to [[17α-hydroxyprogesterone]], a prohormone for [[glucocorticosteroid]]s and [[androstenedione]] through the activity of [[3α-hydroxysteroid dehydrogenase]].

==Neurohormone==
There is some evidence that 17-OH-pregnenolone may have activity as a [[neurohormone]].<ref>Matsunaga M, Ukena K, Baulieu EE, Tsutsui K
7alpha-Hydroxypregnenolone acts as a neuronal activator to stimulate locomotor activity of breeding newts by means of the dopaminergic system. Proc Natl Acad Sci USA 2004 Dec 7;101(49):17282-7. PMID 15569930</ref>


==Clinical use==
==Clinical use==
Measurements of 17-OH-pregnenolone 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>
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.
[http://jcem.endojournals.org/cgi/content/full/87/9/4301]</ref>

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.
== 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]]
* [[Narave pig]], intersex pigs that have low levels of 17α-Hydroxypregnenolone

==Additional images==
<gallery>
File:Steroidogenesis.svg|[[Steroidogenesis]]
</gallery>


== References ==
{{Reflist}}


{{Endogenous steroids}}
==See also==
{{Xenobiotic-sensing receptor modulators}}
[[Congenital adrenal hyperplasia]]


{{DEFAULTSORT:Hydroxypregnenolone, 17α-}}
==References==
<references/>


[[Category:Steroids]]
[[Category:Pregnane X receptor agonists]]
[[Category:Pregnanes]]

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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