17α-Hydroxypregnenolone

Chemical compound changed 477209164 3β,17α-dihydroxypregn-5-en-20-one 17-Hydroxypregnenolone.svg skin-invert-image 250 17-Hidroxipregnenolona3D.png bg-transparent 250 Adrenal, Gonads correct ?? 387-79-1 correct FDA 77ME40334S 3032570 correct drugbank correct chemspider 17215939 changed EBI 28750 21 32 3 CC[C@@]2(O)CC[C@H]1[C@@H]3CCC4CC(O)C(=O)C[C@]4(C)[C@H]3CC[C@@]12C correct chemspider 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 correct chemspider QPLFSAZMHUAMKE-FOCOMJRBSA-N 268 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. Hill M, Lukác D, Lapcík O, Sulcová J, Hampl R, Pouzar V, Stárka L 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 April 1999 10369116 10.1515/CCLM.1999.072 41315909 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-hydroxypregnenolone represents an intermediary in the Δ5 pathway that leads from pregnenolone to DHEA. 17α-Hydroxypregnenolone 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. Riepe FG, Mahler P, Sippell WG, 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 and Metabolism 87 9 4301–6 September 2002 12213889 10.1210/jc.2002-020452 free 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. Tsutsui K, Haraguchi S, Vaudry H 7α-Hydroxypregnenolone regulating locomotor behavior identified in the brain and pineal gland across vertebrates General and Comparative Endocrinology 265 97–105 September 2018 28919448 10.1016/j.ygcen.2017.09.014 5636071 See also Congenital adrenal hyperplasia Narave pig, intersex pigs that have low levels of 17α-Hydroxypregnenolone Additional images References Category:Pregnane X receptor agonists Category:Pregnanes