| Systematic (IUPAC) name | |
|---|---|
| 3β,17-dihydroxypregn-5-en-20-one | |
| Clinical data | |
| Pregnancy cat. | ? |
| Legal status | ? |
| Pharmacokinetic data | |
| Metabolism | Adrenal, Gonads |
| Identifiers | |
| CAS number | 387-79-1 |
| ATC code | ? |
| PubChem | CID 3032570 |
| ChemSpider | 17215939 |
| Chemical data | |
| Formula | C21H32O3 |
| Mol. mass | 332.48 g/mol |
| SMILES | eMolecules & PubChem |
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| Physical data | |
| Melt. point | 268 °C (514 °F) |
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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.
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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.
There is some evidence that 17-OH-pregnenolone may have activity as a neurohormone.[2]
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.
Congenital adrenal hyperplasia
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