17α-Hydroxypregnenolone: Difference between revisions
Updating {{drugbox}} (no changed fields - updated 'ChemSpiderID_Ref', 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEBI_Ref') per [[Wikipedia:WikiProject Chemicals/Chembox validation|Chem/Dru |
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| IUPAC_name = 3β,17-dihydroxypregn-5-en-20-one |
| IUPAC_name = 3β,17-dihydroxypregn-5-en-20-one |
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| image = 17-Hydroxypregnenolone.png |
| image = 17-Hydroxypregnenolone.png |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 17215939 |
| ChemSpiderID = 17215939 |
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| InChI = 1/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 |
| InChI = 1/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 |
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| InChIKey = QPLFSAZMHUAMKE-FOCOMJRBBT |
| InChIKey = QPLFSAZMHUAMKE-FOCOMJRBBT |
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| CASNo_Ref = {{cascite|correct|CAS}} |
| CASNo_Ref = {{cascite|correct|CAS}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 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 |
| StdInChI = 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 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = QPLFSAZMHUAMKE-FOCOMJRBSA-N |
| StdInChIKey = QPLFSAZMHUAMKE-FOCOMJRBSA-N |
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| CAS_number = 387-79-1 |
| CAS_number = 387-79-1 |
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| ATC_suffix = |
| ATC_suffix = |
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| PubChem = 3032570 |
| PubChem = 3032570 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = |
| DrugBank = |
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| C = 21 | H = 32 | O = 3 |
| C = 21 | H = 32 | O = 3 |
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Revision as of 02:26, 8 August 2011
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| Pharmacokinetic data | |
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| Metabolism | Adrenal, Gonads |
| 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 prohormone 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 prohormone 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]