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17α-Hydroxyprogesterone
Chemical compound From Wikipedia, the free encyclopedia
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17α-Hydroxyprogesterone (17α-OHP), also known as 17-OH progesterone (17-OHP),[1] or hydroxyprogesterone (OHP), is an endogenous progestogen steroid hormone related to progesterone.[2][3][4] It is also a chemical intermediate in the biosynthesis of many other endogenous steroids, including androgens, estrogens, glucocorticoids, and mineralocorticoids, as well as neurosteroids.
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Biological activity
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Perspective
17α-OHP is an agonist of the progesterone receptor (PR) similarly to progesterone, albeit weakly in comparison.[5] In addition, it is an antagonist of the mineralocorticoid receptor (MR)[6] as well as a partial agonist of the glucocorticoid receptor (GR), albeit with very low potency (EC50 >100-fold less relative to cortisol) at the latter site, also similarly to progesterone.[5][7][8]
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Biochemistry
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Biosynthesis
17α-OHP is derived from progesterone via 17α-hydroxylase (encoded by CYP17A1).[9]
17α-OHP increases in the third trimester of pregnancy primarily due to fetal adrenal production.[10]
This steroid is primarily produced in the adrenal glands and to some degree in the gonads, specifically the corpus luteum of the ovary. Normal levels are 3-90 ng/dl in children, and in women, 20-100 ng/dl prior to ovulation, and 100-500 ng/dl during the luteal phase.[11][12]
Measurement
Measurements of levels of 17α-OHP are useful in the evaluation of patients with suspected congenital adrenal hyperplasia as the typical enzymes that are defective, namely 21-hydroxylase and 11β-hydroxylase, lead to a build-up of 17α-OHP.[13] In contrast, the rare patient with 17α-hydroxylase deficiency will have very low or undetectable levels of 17α-OHP.[9] 17α-OHP levels can also be used to measure contribution of progestational activity of the corpus luteum during pregnancy as progesterone but note, 17α-OHP is also contributed by the placenta.[14]
Immunoassays like RIA (radioimmunoassay) or IRMA (immunoradiometric assay) used to clinically determine 17α-OHP are prone to cross-reactivity with the 17α-OHP steroid precursors and their sulphated conjugates. Gas or liquid chromatography and mass spectrometry (e.g. LC-MS/MS) achieves greater specificity than immunoassays.[15][16]
Measurement of 17α-OHP by LC-MS/MS improves newborn screening for congenital adrenal hyperplasia due to 21-hydroxylase deficiency, because 17α-OHP steroid precursors and their sulphated conjugates which are present in the first two days after birth and longer in pre-term neonates, cross-react in immunoassays with 17α-OHP, giving falsely high 17α-OHP levels.[15][16]
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Pharmacology
Pharmacokinetics
Although 17α-OHP has not been used as a medication, its pharmacokinetics have been studied and reviewed.[17]
Medical uses
Esters of 17α-OHP, such as hydroxyprogesterone caproate and, to a far lesser extent, hydroxyprogesterone acetate and hydroxyprogesterone heptanoate, have been used in medicine as progestins.[2][3][4]
Chemistry
17α-OHP is the parent compound of a class of progestins referred to as the 17α-hydroxyprogesterone derivatives.[18][19][20] Among others, this class of drugs includes chlormadinone acetate, cyproterone acetate, hydroxyprogesterone caproate, medroxyprogesterone acetate, and megestrol acetate.[18][19][20]
Society and culture
Generic names
Hydroxyprogesterone is the generic name of 17α-OHP and its INN and BAN.[2][3][4]
See also
References
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