Английская Википедия:17α-Hydroxyprogesterone
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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.
Biological activity
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]
Шаблон:Relative affinities of hydroxyprogesterone and related steroids
Biochemistry
Biosynthesis
17α-OHP is derived from progesterone via 17α-hydroxylase (encoded by CYP17A1)Шаблон:Cn
17α-OHP increases in the third trimester of pregnancy primarily due to fetal adrenal production.Шаблон:Cn
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.[9][10]
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. In contrast, the rare patient with 17α-hydroxylase deficiency will have very low or undetectable levels of 17α-OHP. 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.Шаблон:Cn
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.[11][12]
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.[11][12]
Pharmacology
Pharmacokinetics
Although 17α-OHP has not been used as a medication, its pharmacokinetics have been studied and reviewed.[13]
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] When "hydroxyprogesterone" is referenced from the standpoint of medical use, what is usually being referred to is actually, in general, hydroxyprogesterone caproate.Шаблон:Cn
Chemistry
17α-OHP, also known as 17α-hydroxypregn-4-ene-3,20-dione, is a naturally occurring pregnane steroid. It features ketone groups at the C3 and C20 positions, a hydroxyl group at the C17α position, and a double bond between the C4 and C5 positions.Шаблон:Cn
17α-OHP is the parent compound of a class of progestins referred to as the 17α-hydroxyprogesterone derivatives.[14][15][16] Among others, this class of drugs includes chlormadinone acetate, cyproterone acetate, hydroxyprogesterone caproate, medroxyprogesterone acetate, and megestrol acetate.[14][15][16]
Society and culture
Generic names
Hydroxyprogesterone is the generic name of 17α-OHP and its Шаблон:Abbrlink and Шаблон:Abbrlink.[2][3][4]
See also
- 11α-Hydroxyprogesterone
- 5α-Dihydroprogesterone
- 20-Dihydroprogesterone
- 11-Deoxycorticosterone
- 11-Deoxycortisol
- 17α-Methylprogesterone
- 19-Norprogesterone
- 19-Nortestosterone
References
Шаблон:Endogenous steroids Шаблон:Progestogens and antiprogestogens Шаблон:Navboxes
- ↑ Шаблон:Cite web
- ↑ 2,0 2,1 2,2 Шаблон:Cite book
- ↑ 3,0 3,1 3,2 Шаблон:Cite book
- ↑ 4,0 4,1 4,2 Шаблон:Cite book
- ↑ 5,0 5,1 Шаблон:Cite journal
- ↑ Шаблон:Cite journal
- ↑ Шаблон:Cite journal
- ↑ Шаблон:Cite journal
- ↑ Reference Values During Pregnancy
- ↑ Шаблон:Cite web
- ↑ 11,0 11,1 Шаблон:Cite journal
- ↑ 12,0 12,1 Шаблон:Cite journal
- ↑ Шаблон:Cite book
- ↑ 14,0 14,1 Шаблон:Cite book
- ↑ 15,0 15,1 Шаблон:Cite book
- ↑ 16,0 16,1 Шаблон:Cite book
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