17-Hydroxypregnenolone

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17-Hydroxypregnenolone
Pharmacokinetic data
Metabolism	AdrenalGonads
Identifiers
	IUPAC name 3β,17-dihydroxypregn-5-en-20-one;
CAS Number	387-79-1;
PubChem CID	3032570;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C21H32O3
Molar mass	332.48 g/mol
Melting point	268 °C (514.4 °F)

Overview

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.

Additional images

Steroidogenesis

References

↑ 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
↑ 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
↑ 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]

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[1] 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

[2] 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

[3] 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]

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