17α-Hydroxyprogesterone

Hydroxyprogesterone Hydroxyprogesterone caproate Hydroxyprogesterone acetate vanc 17-Hydroxyprogesterone.svg skin-invert-image 225 17-Hidroxiprogesterona3D.png bg-transparent 225 17α-Hydroxypregn-4-ene-3,20-dione (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 Hydroxyprogesterone (INN International Nonproprietary Name) 68-96-2 6238 6002 21807M87J2 17252 1062 D08052 5104 CC(=O)[C@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C)O 1S/C21H30O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h12,16-18,24H,4-11H2,1-3H3/t16-,17+,18+,19+,20+,21+/m1/s1 DBPWSSGDRRHUNT-CEGNMAFCSA-N C21H30O3 330.46 g/mol 219.5 17α-Hydroxyprogesterone (17α-OHP), also known as 17-OH progesterone (17-OHP),https://www.gloshospitals.nhs.uk/our-services/services-we-offer/pathology/tests-and-investigations/17-hydroxyprogesterone-17ohp/ 17-hydroxyprogesterone (17OHP) or hydroxyprogesterone (OHP), is an endogenous progestogen steroid hormone related to progesterone.J. Elks The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA665 14 November 2014 Springer 978-1-4757-2085-3 664–665I.K. Morton Judith M. Hall Concise Dictionary of Pharmacological Agents: Properties and Synonyms https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA146 6 December 2012 Springer Science & Business Media 978-94-011-4439-1 146–Index Nominum 2000: International Drug Directory https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA532 January 2000 Taylor & Francis 978-3-88763-075-1 532– 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. Attardi BJ, Zeleznik A, Simhan H, Chiao JP, Mattison DR, Caritis SN Comparison of progesterone and glucocorticoid receptor binding and stimulation of gene expression by progesterone, 17-alpha hydroxyprogesterone caproate, and related progestins Am. J. Obstet. Gynecol. 197 6 599.e1–7 2007 18060946 2278032 10.1016/j.ajog.2007.05.024 In addition, it is an antagonist of the mineralocorticoid receptor (MR) Mooij CF, Parajes S, Pijnenburg-Kleizen KJ, Arlt W, Krone N, Claahsen-van der Grinten HL Influence of 17-Hydroxyprogesterone, Progesterone and Sex Steroids on Mineralocorticoid Receptor Transactivation in Congenital Adrenal Hyperplasia Horm Res Paediatr 83 6 414–421 April 2015 25896481 10.1159/000374112 24727940 http://pure-oai.bham.ac.uk/ws/files/25244128/Mooij_et_al_Influence_17_Hydroxyprogesterone_Hormone_Research_Paediatrics_2015_Post_Print.pdf 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. Pijnenburg-Kleizen KJ, Engels M, Mooij CF, Griffin A, Krone N, Span PN, van Herwaarden AE, Sweep FC, Claahsen-van der Grinten HL Adrenal Steroid Metabolites Accumulating in Congenital Adrenal Hyperplasia lead to Transactivation of the Glucocorticoid Receptor Endocrinology 156 10 3504–3510 2015 26207344 10.1210/en.2015-1087 free Sun Kang Lei Kaiyu Chen Li Georgiou Ektoras X. Sooranna Suren R. Khanjani Shirin Brosens Jan J. Bennett Phillip R. Johnson Mark R. Progesterone Acts via the Nuclear Glucocorticoid Receptor to Suppress IL-1β-Induced COX-2 Expression in Human Term Myometrial Cells PLOS ONE 7 11 2012 e50167 1932-6203 10.1371/journal.pone.0050167 23209664 3509141 2012PLoSO...750167L free Biochemistry thumb|left|300px|class=skin-invert-image|Steroidogenesis, showing 17α-OHP around the left-middle among the pregnenes. Biosynthesis 17α-OHP is derived from progesterone via 17α-hydroxylase (encoded by CYP17A1).Kim Sung Mee Rhee Jeong Ho A case of 17 alpha-hydroxylase deficiency Clinical and Experimental Reproductive Medicine The Korean Society for Reproductive Medicine 42 2 2015 72–76 2233-8233 10.5653/cerm.2015.42.2.72 26161337 4496435 17α-OHP increases in the third trimester of pregnancy primarily due to fetal adrenal production.Tal Reshef Taylor Hugh S. Endocrinology of Pregnancy MDText.com, Inc. 2021-03-18 25905197 https://www.ncbi.nlm.nih.gov/books/NBK278962/ 2024-06-25 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.Reference Values During Pregnancyhttp://www.keratin.com/ab/ab012.shtml normal ranges for hormone tests in women 2011-08-07 2020-11-08 https://web.archive.org/web/20201108215852/https://www.keratin.com/ab/ab012.shtml dead 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.Held Patrice K. Bird Ian M. Heather Natasha L. Newborn Screening for Congenital Adrenal Hyperplasia: Review of Factors Affecting Screening Accuracy International Journal of Neonatal Screening MDPI AG 6 3 2020-08-23 2409-515X 10.3390/ijns6030067 free 67 33117906 7569755 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.Check J. H. Vaze M. M. Epstein R. Wu C. H. Quattrocchi J. Vetter B. 17-Hydroxyprogesterone level as a marker for corpus luteum function in aborters versus nonaborters International Journal of Fertility 35 2 1990 0020-725X 1970979 112–115 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. de Hora MR, Heather NL, Patel T, Bresnahan LG, Webster D, Hofman PL Measurement of 17-Hydroxyprogesterone by LCMSMS Improves Newborn Screening for CAH Due to 21-Hydroxylase Deficiency in New Zealand International Journal of Neonatal Screening 6 1 6 March 2020 33073005 7422986 10.3390/ijns6010006 free Bialk ER, Lasarev MR, Held PK Wisconsin's Screening Algorithm for the Identification of Newborns with Congenital Adrenal Hyperplasia International Journal of Neonatal Screening 5 3 33 September 2019 33072992 7510207 10.3390/ijns5030033 free 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. Pharmacology Pharmacokinetics Although 17α-OHP has not been used as a medication, its pharmacokinetics have been studied and reviewed.Die Gestagene https://books.google.com/books?id=t8GpBgAAQBAJ&pg=PA276 27 November 2013 Springer-Verlag 978-3-642-99941-3 276–277 Medical uses Hydroxyprogesterone caproate Hydroxyprogesterone acetate Hydroxyprogesterone heptanoate 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. Chemistry List of progestogens 17α-OHP is the parent compound of a class of progestins referred to as the 17α-hydroxyprogesterone derivatives.Jeffrey K. Aronson Meyler's Side Effects of Endocrine and Metabolic Drugs https://books.google.com/books?id=BWMeSwVwfTkC&pg=PA289 21 February 2009 Elsevier 978-0-08-093292-7 289–Robert Alan Prentky Ann Wolbert Burgess Forensic Management of Sexual Offenders https://books.google.com/books?id=-50Of8_n_TAC&pg=PA219 31 July 2000 Springer Science & Business Media 978-0-306-46278-8 219–H. J. Smith Hywel Williams Introduction to the Principles of Drug Design https://books.google.com/books?id=mElhDAAAQBAJ&pg=PA187 1 January 1983 Elsevier 978-1-4831-8350-3 187– Among others, this class of drugs includes chlormadinone acetate, cyproterone acetate, hydroxyprogesterone caproate, medroxyprogesterone acetate, and megestrol acetate. Society and culture Generic names Hydroxyprogesterone is the generic name of 17α-OHP and its INN International Nonproprietary Name and BAN British Approved Name. See also 11α-Hydroxyprogesterone 5α-Dihydroprogesterone 20-Dihydroprogesterone 11-Deoxycorticosterone 11-Deoxycortisol 17α-Methylprogesterone 19-Norprogesterone 19-Nortestosterone References Biological activity background:#ccccff Category:Antimineralocorticoids Category:Diketones Category:Glucocorticoids Category:Gynaecological endocrinology Category:Metabolic intermediates Category:Pregnane X receptor agonists Category:Pregnanes Category:Progestogens