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| Names | |
|---|---|
| IUPAC name 17α-Hydroxypregn-4-ene-3,20-dione | |
| Systematic IUPAC name (1R,3aS,3bR,9aR,9bS,11aS)-1-Acetyl-1-hydroxy-9a,11a-dimethyl-1,2,3,3a,3b,4,5,8,9,9a,9b,10,11,11a-tetradecahydro-7H-cyclopenta[a]phenanthren-7-one | |
| Other names | |
| Identifiers | |
3D model (JSmol) | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.000.636 |
| KEGG | |
| UNII | |
| |
| |
| Properties | |
| C21H30O3 | |
| Molar mass | 330.46 g/mol |
| Melting point | 219.5 |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
17α-Hydroxyprogesterone (17α-OHP), also known as17-OH progesterone (17-OHP),[1] orhydroxyprogesterone (OHP), is anendogenousprogestogensteroid hormone related toprogesterone.[2][3][4] It is also achemical intermediate in thebiosynthesis of many other endogenous steroids, includingandrogens,estrogens,glucocorticoids, andmineralocorticoids, as well asneurosteroids.
17α-OHP is anagonist of theprogesterone receptor (PR) similarly to progesterone, albeit weakly in comparison.[5] In addition, it is anantagonist of themineralocorticoid receptor (MR)[6] as well as apartial agonist of theglucocorticoid receptor (GR), albeit with very low potency (EC50 >100-fold less relative tocortisol) at the latter site, also similarly to progesterone.[5][7][8]
| Compound | hPR-A | hPR-B | rbPR | rbGR | rbER | |||
|---|---|---|---|---|---|---|---|---|
| Progesterone | 100 | 100 | 100 | <1 | <1 | |||
| 17α-Hydroxyprogesterone | 1 | 1 | 3 | 1 | <1 | |||
| Hydroxyprogesterone caproate | 26 | 30 | 28 | 4 | <1 | |||
| Hydroxyprogesterone acetate | 38 | 46 | 115 | 3 | ? | |||
| Notes: Values are percentages (%). Referenceligands (100%) wereprogesterone for thePRTooltip progesterone receptor,dexamethasone for theGRTooltip glucocorticoid receptor, andestradiol for theERTooltip estrogen receptor.Sources: See template. | ||||||||
17α-OHP is derived fromprogesterone via17α-hydroxylase (encoded byCYP17A1).[9]
17α-OHP increases in the third trimester ofpregnancy primarily due to fetal adrenal production.[10]
This steroid is primarily produced in theadrenal glands and to some degree in thegonads, specifically thecorpus luteum of theovary. Normal levels are 3-90 ng/dl in children, and in women, 20-100 ng/dl prior toovulation, and 100-500 ng/dl during theluteal phase.[11][12]
Measurements of levels of 17α-OHP are useful in the evaluation of patients with suspectedcongenital adrenal hyperplasia as the typical enzymes that are defective, namely21-hydroxylase and11β-hydroxylase, lead to a build-up of 17α-OHP.[13] In contrast, the rare patient with17α-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 theplacenta.[14]
Immunoassays like RIA (radioimmunoassay) or IRMA (immunoradiometricassay) used to clinically determine 17α-OHP are prone to cross-reactivity with the 17α-OHP steroid precursors and their sulphated conjugates.Gas orliquid chromatography andmass spectrometry (e.g. LC-MS/MS) achieves greater specificity than immunoassays.[15][16]
Measurement of 17α-OHP by LC-MS/MS improves newborn screening forcongenital 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]
Although 17α-OHP has not been used as a medication, itspharmacokinetics have been studied and reviewed.[17]
Esters of 17α-OHP, such ashydroxyprogesterone caproate and, to a far lesser extent,hydroxyprogesterone acetate andhydroxyprogesterone heptanoate, have been used in medicine asprogestins.[2][3][4]
17α-OHP is the parent compound of a class of progestins referred to as the17α-hydroxyprogesterone derivatives.[18][19][20] Among others, this class of drugs includeschlormadinone acetate,cyproterone acetate,hydroxyprogesterone caproate,medroxyprogesterone acetate, andmegestrol acetate.[18][19][20]
Hydroxyprogesterone is thegeneric name of 17α-OHP and itsINNTooltip International Nonproprietary Name andBANTooltip British Approved Name.[2][3][4]