17α-Hydroxypregnenolone: Difference between revisions
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'''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 [[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 | pmid = 10369116 }}</ref> High levels are also achieved during [[pregnancy]]. |
'''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 [[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]]. |
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==Prohormone== |
==Prohormone== |
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==Neurohormone== |
==Neurohormone== |
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There is some evidence that 17-OH-pregnenolone may have activity as a [[neurohormone]].<ref>{{cite journal | pmid = 15569930 }}</ref> |
There is some evidence that 17-OH-pregnenolone may have activity as a [[neurohormone]].<ref>{{cite journal | last1 = Matsunaga | first1 = M | last2 = Ukena | first2 = K | last3 = Baulieu | first3 = EE | last4 = Tsutsui | first4 = K | title = 7alpha-Hydroxypregnenolone acts as a neuronal activator to stimulate locomotor activity of breeding newts by means of the dopaminergic system | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 101 | issue = 49 | pages = 17282–7 | year = 2004 | pmid = 15569930 | pmc = 535386 | doi = 10.1073/pnas.0407176101 }}</ref> |
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==Clinical use== |
==Clinical use== |
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Revision as of 20:03, 14 November 2010
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| Pharmacokinetic data | |
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| Metabolism | AdrenalGonads |
| Identifiers | |
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| CAS Number | |
| PubChem CID | |
| ChemSpider | |
| 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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| (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 considered a prohormone in the formation of dehydroepiandrosterone (DHEA), itself a prohomone 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 prohomone 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
- ^ 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.
- ^ Matsunaga, M; Ukena, K; Baulieu, EE; Tsutsui, K (2004). "7alpha-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.
- ^ 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]