17α-hydroxypregnenolone

17α-Hydroxypregnenolone

Pharmacokinetic data
Metabolism	Adrenal, Gonads
Identifiers
IUPAC name 3β,17α-dihydroxypregn-5-en-20-one
CAS Number	387-79-1 Y
PubChem CID	3032570
ChemSpider	17215939 Y
ChEBI	CHEBI:28750 N
ECHA InfoCard	100.006.239
Chemical and physical data
Formula	C21H32O3
Molar mass	332.48 g/mol
3D model (Jmol)	Interactive image
Melting point	268 °C (514 °F)
SMILES CC[C@@]2(O)CC[C@H]1[C@@H]3CCC4CC(O)C(=O)C[C@]4(C)[C@H]3CC[C@@]12C
InChI 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 Y Key:QPLFSAZMHUAMKE-FOCOMJRBSA-N Y
NY (what is this?)

17α-Hydroxypregnenolone is a pregnane (C21) steroid that is obtained by hydroxylation of pregnenolone at the C17α position. This step is performed by the 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. High levels are also achieved during pregnancy.

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.

There is some evidence that 17α-hydroxypregnenolone may have activity as a neurosteroid.

Measurements of 17α-hydroxypregnenolone are useful in the diagnosis of certain forms of congenital adrenal hyperplasia. 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.