17α-Hydroxypregnenolone: Difference between revisions
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==Clinical use== |
==Clinical use== |
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Measurements of 17α-hydroxypregnenolone are useful in the diagnosis of certain forms of [[congenital adrenal hyperplasia]].<ref> |
Measurements of 17α-hydroxypregnenolone are useful in the diagnosis of certain forms of [[congenital adrenal hyperplasia]].<ref>{{Cite journal |doi = 10.1210/jc.2002-020452|pmid = 12213889|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 & Metabolism|volume = 87|issue = 9|pages = 4301–4306|year = 2002|last1 = Riepe|first1 = Felix G.|last2 = Mahler|first2 = Philip|last3 = Sippell|first3 = Wolfgang G.|last4 = Partsch|first4 = Carl-Joachim}}</ref> |
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[http://jcem.endojournals.org/cgi/content/full/87/9/4301] {{Webarchive|url=https://web.archive.org/web/20110516204902/http://jcem.endojournals.org/cgi/content/full/87/9/4301 |date=2011-05-16 }}</ref> |
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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. |
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Revision as of 17:29, 25 January 2020
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| Pharmacokinetic data | |
|---|---|
| Metabolism | Adrenal, Gonads |
| Identifiers | |
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| CAS Number | |
| PubChem CID | |
| ChemSpider | |
| ChEBI | |
| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.006.239 |
| Chemical and physical data | |
| Formula | C21H32O3 |
| Molar mass | 332.48 g/mol g·mol−1 |
| 3D model (JSmol) | |
| Melting point | 268 °C (514 °F) |
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  (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
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
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
17α-hydroxypregnenolone is a known neuromodulator as its acts in the central nervous system. Specifically, it is known to modulate locomotion.[3]
See also
Additional images
References
- ^ 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. 37 (4): 439–47. doi:10.1515/CCLM.1999.072. PMID 10369116.
- ^ Riepe, Felix G.; Mahler, Philip; Sippell, Wolfgang G.; Partsch, Carl-Joachim (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 & Metabolism. 87 (9): 4301–4306. doi:10.1210/jc.2002-020452. PMID 12213889.
- ^ Tsutsui, Kazuyoshi; Haraguchi, Shogo; Vaudry, Hubert (1 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. ISSN 1095-6840. PMID 28919448.