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17α-Hydroxypregnenolone

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.

17α-Hydroxypregnenolone
Pharmacokinetic data
MetabolismAdrenal, Gonads
Identifiers
  • 3β,17α-dihydroxypregn-5-en-20-one
CAS Number
  • 387-79-1 Y
PubChem CID
  • 3032570
ChemSpider
  • 17215939 Y
UNII
  • 77ME40334S
ChEBI
  • CHEBI:28750 N
CompTox Dashboard (EPA)
  • DTXSID20894988
ECHA InfoCard100.006.239
Chemical and physical data
FormulaC21H32O3
Molar mass332.484 g·mol−1
3D model (JSmol)
  • Interactive image
Melting point268 °C (514 °F)
  • CC[C@@]2(O)CC[C@H]1[C@@H]3CCC4CC(O)C(=O)C[C@]4(C)[C@H]3CC[C@@]12C
  • 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?)  (verify)

Prohormone Edit

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 Edit

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 Edit

17α-hydroxypregnenolone is a known neuromodulator as its acts in the central nervous system. Specifically, it is known to modulate locomotion.[3]

See also Edit

Additional images Edit

References Edit

  1. ^ Hill M, Lukác D, Lapcík O, Sulcová J, Hampl R, Pouzar V, Stárka L (April 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. S2CID 41315909.
  2. ^ Riepe FG, Mahler P, Sippell WG, Partsch CJ (September 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 and Metabolism. 87 (9): 4301–6. doi:10.1210/jc.2002-020452. PMID 12213889.
  3. ^ Tsutsui K, Haraguchi S, Vaudry H (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. PMID 28919448. S2CID 5636071.

17α, hydroxypregnenolone, pregnane, steroid, that, obtained, hydroxylation, pregnenolone, c17α, position, this, step, performed, mitochondrial, cytochrome, p450, enzyme, 17α, hydroxylase, cyp17a1, that, present, adrenal, gonads, peak, levels, reached, humans, . 17a Hydroxypregnenolone is a pregnane C21 steroid that is obtained by hydroxylation of pregnenolone at the C17a position This step is performed by the mitochondrial cytochrome P450 enzyme 17a 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 17a HydroxypregnenolonePharmacokinetic dataMetabolismAdrenal GonadsIdentifiersIUPAC name 3b 17a dihydroxypregn 5 en 20 oneCAS Number387 79 1 YPubChem CID3032570ChemSpider17215939 YUNII77ME40334SChEBICHEBI 28750 NCompTox Dashboard EPA DTXSID20894988ECHA InfoCard100 006 239Chemical and physical dataFormulaC 21H 32O 3Molar mass332 484 g mol 13D model JSmol Interactive imageMelting point268 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 12CInChI 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 YKey QPLFSAZMHUAMKE FOCOMJRBSA N Y N Y what is this verify Contents 1 Prohormone 2 Clinical use 3 Neurosteroid 4 See also 5 Additional images 6 ReferencesProhormone Edit17a 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 17a hydroxypregenolone represents an intermediary in the D5 pathway that leads from pregnenolone to DHEA 17a Hydroxypregneolone is also converted to 17a hydroxyprogesterone a prohormone for glucocorticosteroids and androstenedione through the activity of 3a hydroxysteroid dehydrogenase Clinical use EditMeasurements of 17a hydroxypregnenolone are useful in the diagnosis of certain forms of congenital adrenal hyperplasia 2 In patients with congenital adrenal hyperplasia due to 3b hydroxysteroid dehydrogenase deficiency 17a hydroxypregnenolone is increased while in patients with congenital adrenal hyperplasia due to 17a hydroxylase deficiency levels are low to absent Neurosteroid Edit17a hydroxypregnenolone is a known neuromodulator as its acts in the central nervous system Specifically it is known to modulate locomotion 3 See also EditCongenital adrenal hyperplasia Narave pig intersex pigs that have low levels of 17a HydroxypregnenoloneAdditional images Edit SteroidogenesisReferences Edit Hill M Lukac D Lapcik O Sulcova J Hampl R Pouzar V Starka L April 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 S2CID 41315909 Riepe FG Mahler P Sippell WG Partsch CJ September 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 and Metabolism 87 9 4301 6 doi 10 1210 jc 2002 020452 PMID 12213889 Tsutsui K Haraguchi S Vaudry H September 2018 7a 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 PMID 28919448 S2CID 5636071 Retrieved from https en wikipedia org w index php title 17a Hydroxypregnenolone amp oldid 1143599011, wikipedia, wiki, book, books, library,

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