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( d i f f ) ← P r e v i o u s r e v i s i o n | L a t e s t r e v i s i o n ( d i f f ) | N e w e r r e v i s i o n → ( d i f f )
17α-Hydroxyprogesterone
Names
IUPAC name
17α-Hydroxypregn-4-ene-3,20-dione
Systematic IUPAC name
(1 R ,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
Hydroxyprogesterone (INN Tooltip International Nonproprietary Name )
Identifiers
CAS Number
3D model (JSmol )
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
100.000.636
IUPHAR/BPS
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA )
InChI=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
Key: DBPWSSGDRRHUNT-CEGNMAFCSA-N
CC(=O)[C@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C)O
Properties
Chemical formula
C 21 H 30 O 3
Molar mass
330.46 g/mol
Melting point
219.5
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound
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 (EC 50 >100-fold less relative to cortisol ) at the latter site, also similarly to progesterone.[5] [7] [8]
Biochemistry
Steroidogenesis , showing 17α-OHP around the left-middle among the pregnenes .
Biosynthesis
17α-OHP is derived from progesterone via 17α-hydroxylase (encoded by CYP17A1 )[citation needed ]
17α-OHP increases in the third trimester of pregnancy primarily due to fetal adrenal production.[citation needed ]
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 .[citation needed ]
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.[citation needed ]
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.[citation needed ]
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 INN Tooltip International Nonproprietary Name and BAN Tooltip British Approved Name .[2] [3] [4]
See also
References
^ a b c I.K. Morton, Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms . Springer Science & Business Media. pp. 146–. ISBN 978-94-011-4439-1 .
^ a b c Index Nominum 2000: International Drug Directory . Taylor & Francis. January 2000. pp. 532–. ISBN 978-3-88763-075-1 .
^ a b Attardi BJ, Zeleznik A, Simhan H, Chiao JP, Mattison DR, Caritis SN (2007). "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. doi :10.1016/j.ajog.2007.05.024 . PMC 2278032 . PMID 18060946 .
^ Mooij CF, Parajes S, Pijnenburg-Kleizen KJ, Arlt W, Krone N, Claahsen-van der Grinten HL (April 2015). "Influence of 17-Hydroxyprogesterone, Progesterone and Sex Steroids on Mineralocorticoid Receptor Transactivation in Congenital Adrenal Hyperplasia" (PDF) . Horm Res Paediatr . 83 (6 ): 414–421. doi :10.1159/000374112 . PMID 25896481 . S2CID 24727940 .
^ Pijnenburg-Kleizen KJ, Engels M, Mooij CF, Griffin A, Krone N, Span PN, van Herwaarden AE, Sweep FC, Claahsen-van der Grinten HL (2015). "Adrenal Steroid Metabolites Accumulating in Congenital Adrenal Hyperplasia lead to Transactivation of the Glucocorticoid Receptor" . Endocrinology . 156 (10 ): 3504–3510. doi :10.1210/en.2015-1087 . PMID 26207344 .
^ Sun K, Lei K, Chen L, Georgiou EX, Sooranna SR, Khanjani S, Brosens JJ, Bennett PR, Johnson MR (2012). "Progesterone Acts via the Nuclear Glucocorticoid Receptor to Suppress IL-1β-Induced COX-2 Expression in Human Term Myometrial Cells" . PLOS ONE . 7 (11 ): e50167. Bibcode :2012PLoSO...750167L . doi :10.1371/journal.pone.0050167 . ISSN 1932-6203 . PMC 3509141 . PMID 23209664 .
^ Reference Values During Pregnancy
^ "normal ranges for hormone tests in women" . Archived from the original on 2020-11-08. Retrieved 2011-08-07 .
^ a b de Hora MR, Heather NL, Patel T, Bresnahan LG, Webster D, Hofman PL (March 2020). "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. doi :10.3390/ijns6010006 . PMC 7422986 . PMID 33073005 .
^ a b Bialk ER, Lasarev MR, Held PK (September 2019). "Wisconsin's Screening Algorithm for the Identification of Newborns with Congenital Adrenal Hyperplasia" . International Journal of Neonatal Screening . 5 (3 ): 33. doi :10.3390/ijns5030033 . PMC 7510207 . PMID 33072992 .
^ Die Gestagene . Springer-Verlag. 27 November 2013. pp. 276–277. ISBN 978-3-642-99941-3 .
^ a b Jeffrey K. Aronson (21 February 2009). Meyler's Side Effects of Endocrine and Metabolic Drugs . Elsevier. pp. 289–. ISBN 978-0-08-093292-7 .
^ a b Robert Alan Prentky, Ann Wolbert Burgess (31 July 2000). Forensic Management of Sexual Offenders . Springer Science & Business Media. pp. 219–. ISBN 978-0-306-46278-8 .
^ a b H. J. Smith, Hywel Williams (1 January 1983). Introduction to the Principles of Drug Design . Elsevier. pp. 187–. ISBN 978-1-4831-8350-3 .
t
e
PR Tooltip Progesterone receptor
Agonists
Testosterone derivatives: Progestins: 6,6-Difluoronorethisterone
6,6-Difluoronorethisterone acetate
17α-Allyl-19-nortestosterone
Allylestrenol
Altrenogest
Chloroethynylnorgestrel
Cingestol
Danazol
Desogestrel
Dienogest
Ethinylandrostenediol
Ethisterone
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Etonogestrel
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Etynodiol diacetate
Gestodene
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Norgestimate
Norgestrel
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Norvinisterone
Oxendolone
Quingestanol
Quingestanol acetate
Tibolone
Tigestol
Tosagestin ; Anabolic–androgenic steroids: 11β-Methyl-19-nortestosterone
11β-Methyl-19-nortestosterone dodecylcarbonate
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19-Nordehydroepiandrosterone
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Bolandiol dipropionate
Bolandione
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RU-2309
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mPR Tooltip Membrane progesterone receptor (PAQR Tooltip Progestin and adipoQ receptor )
See also
Receptor/signaling modulators
Progestogens and antiprogestogens
Androgen receptor modulators
Estrogen receptor modulators
List of progestogens
R e t r i e v e d f r o m " https://en.wikipedia.org/w/index.php?title=17α-Hydroxyprogesterone&oldid=1198514337 "
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