17α-ヒドロキシプレグネノロン
WordNet
- first in order of importance; "the alpha male in the group of chimpanzees"; "the alpha star in a constellation is the brightest or main star"
- the 1st letter of the Greek alphabet
- the beginning of a series or sequence; "the Alpha and Omega, the first and the last, the beginning and the end"--Revelations
- early testing stage of a software or hardware product; "alpha version"
- any high mountain
PrepTutorEJDIC
- アルファ(ギリシア語アルファベットの第1字A,α;英語のA,aに相当) / アルファ星(星座の主星)
- 高山,高峰
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/08/10 10:00:22」(JST)
[Wiki en表示]
17-Hydroxypregnenolone
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| Systematic (IUPAC) name |
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3β,17-dihydroxypregn-5-en-20-one
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| Pharmacokinetic data |
| Metabolism |
Adrenal, Gonads |
| Identifiers |
| CAS Registry Number |
387-79-1 Y |
| PubChem |
CID: 3032570 |
| ChemSpider |
17215939 Y |
| ChEBI |
CHEBI:28750 N |
| Chemical data |
| Formula |
C21H32O3 |
| Molecular mass |
332.48 g/mol |
SMILES
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CC[C@@]2(O)CC[C@H]1[C@@H]3CCC4CC(O)C(=O)C[C@]4(C)[C@H]3CC[C@@]12C
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InChI
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InChI=1S/C21H34O3/c1-4-21(24)10-8-16-14-6-5-13-11-17(22)18(23)12-19(13,2)15(14)7-9-20(16,21)3/h13-17,22,24H,4-12H2,1-3H3/t13?,14-,15+,16+,17?,19+,20+,21-/m1/s1 Y
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Key:QPLFSAZMHUAMKE-FOCOMJRBSA-N Y
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| Physical data |
| Melting point |
268 °C (514 °F) |
| N (what is this?) (verify) |
17-Hydroxypregnenolone (also 17-OH-pregnenolone and 17α-hydroxypregnenolone), is a C21 steroid that is obtained by hydroxylation of pregnenolone at the C17α position. This step is performed by the mitochondrial cytochrome P450 enzyme 17α-hydroxylase (CYP17A1) that is present in the adrenal and gonads. Peak levels are reached in humans at the end of puberty and then decline.[1] High levels are also achieved during pregnancy.
Contents
- 1 Prohormone
- 2 Neurohormone
- 3 Clinical use
- 4 See also
- 5 Additional images
- 6 References
Prohormone
17 OH–pregnenolone is converted from pregnenolone and gives rise to DHEA (below) and to 17 OH-progesterone (to its right)
17-OH-pregnenolone is considered a prohormone in the formation of dehydroepiandrosterone (DHEA), itself a prohormone of the sex steroids.
This conversion is mediated by the enzyme 17,20 lyase. As such 17-OH-pregenolone represents an intermediary in the delta-5-pathway that leads from pregnenolone to DHEA. 17-hydroxypregneolone is also converted to 17-hydroxyprogesterone, a prohormone for glucocorticosteroids and androstenedione through the activity of 3-hydroxysteroid dehydrogenase.
Neurohormone
There is some evidence that 17-OH-pregnenolone may have activity as a neurosteroid.[2]
Clinical use
Measurements of 17-OH-pregnenolone are useful in the diagnosis of certain forms of congenital adrenal hyperplasia.[3] In patients with congenital adrenal hyperplasia due to 3 beta-hydroxysteroid dehydrogenase deficiency 17-OH-pregnenolone is increased, while in patients with congenital adrenal hyperplasia due to 17 alpha-hydroxylase deficiency levels are low to absent.
See also
Congenital adrenal hyperplasia
Additional images
References
- ^ Hill, M; Lukác, D; Lapcík, O; Sulcová, J; Hampl, R; Pouzar, V; Stárka, L (1999). "Age relationships and sex differences in serum levels of pregnenolone and 17-hydroxypregnenolone in healthy subjects". Clinical chemistry and laboratory medicine : CCLM / FESCC 37 (4): 439–47. doi:10.1515/CCLM.1999.072. PMID 10369116.
- ^ Matsunaga, M; Ukena, K; Baulieu, EE; Tsutsui, K (2004). "7α-Hydroxypregnenolone acts as a neuronal activator to stimulate locomotor activity of breeding newts by means of the dopaminergic system". Proceedings of the National Academy of Sciences of the United States of America 101 (49): 17282–7. doi:10.1073/pnas.0407176101. PMC 535386. PMID 15569930.
- ^ Riepe FG, Mahler P, Sippell, Partsch CJ. Longitudinal Study of Plasma Pregnenolone and 17-Hydroxypregnenolone in Full-Term and Preterm Neonates at Birth and during the Early Neonatal Period. The Journal of Clinical Endocrinology & Metabolism (2002) 87: 4301-4306 [1]
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Androgenics
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Receptor
(ligands) |
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AR
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Agonists
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Mixed (SARMs)
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- AC-262,356
- Andarine
- BMS-564,929
- Enobosarm
- LGD-2226
- LGD-3303
- LGD-4033
- S-23
- S-40503
- TFM-4AS-1
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Antagonists
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- 3α-Hydroxytibolone
- 3β-Hydroxytibolone
- Abiraterone
- Abiraterone acetate
- ARN-509
- Benorterone
- Bicalutamide
- BMS-641,988
- BOMT
- Canrenoic acid
- Canrenone
- Chlormadinone acetate
- Cimetidine
- Cioteronel
- Cyproterone
- Cyproterone acetate
- Delanterone
- Dienogest
- Drospirenone
- Enzalutamide
- Epitestosterone
- Flutamide
- Galeterone
- Hydroxyflutamide
- Inocoterone
- Ketoconazole
- Megestrol acetate
- Metogest
- Mifepristone
- Nilutamide
- Nomegestrol
- Nordinone
- Norgestimate
- Osaterone
- Oxendolone
- PF-998425
- Potassium canrenoate
- R2956
- Rosterolone
- RU-58642
- RU-58841
- Spironolactone
- Topilutamide (fluridil)
- Topterone
- Zanoterone
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| Enzyme |
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Modulators
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- 20,22-desmolase, 17α-hydroxylase/17,20-lyase, 3β-HSD, 17β-HSD, 5α-reductase, and aromatase) (see also Steroid hormone metabolism modulator)
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| Others |
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Precursors/prohormones
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- Cholesterol
- 22R-Hydroxycholesterol
- 20α,22R-Dihydroxycholesterol
- Pregnenolone
- Pregnenolone sulfate
- 17-Hydroxypregnenolone
- Progesterone
- 17-Hydroxyprogesterone
- 11-Deoxycortisol (cortodoxone)
- DHEA
- DHEA sulfate
- 5-Androstenediol
- 4-Androstenedione
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Indirect
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- Antigonadotropins (e.g., estrogens, progestogens, prolactin)
- GnRH agonists (e,g, GnRH, leuprorelin)
- GnRH antagonists (e.g., cetrorelix)
- Gonadotropins (e.g., FSH, hCG, LH)
- Kisspeptin
- Plasma proteins (ABP, albumin, SHBG)
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See also: Estrogenics • Glucocorticoids • Mineralocorticoids • Progestogenics
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UpToDate Contents
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English Journal
- Human steroid and oxysterol 7α-hydroxylase CYP7B1: substrate specificity, azole binding and misfolding of clinically relevant mutants.
- Yantsevich AV1, Dichenko YV, Mackenzie F, Mukha DV, Baranovsky AV, Gilep AA, Usanov SA, Strushkevich NV.
- The FEBS journal.FEBS J.2014 Mar;281(6):1700-13. doi: 10.1111/febs.12733. Epub 2014 Feb 20.
- Oxysterols and neurosteroids are important signaling molecules produced by monooxygenases of the cytochrome P450 family that realize their effect through nuclear receptors. CYP7B1 catalyzes the 6- or 7-hydroxylation of both steroids and oxysterols and thus is involved in the metabolism of neurostero
- PMID 24491228
- Brain and pineal 7α-hydroxypregnenolone stimulating locomotor activity: identification, mode of action and regulation of biosynthesis.
- Tsutsui K1, Haraguchi S, Fukada Y, Vaudry H.
- Frontiers in neuroendocrinology.Front Neuroendocrinol.2013 Aug;34(3):179-89. doi: 10.1016/j.yfrne.2013.05.002. Epub 2013 May 16.
- Biologically active steroids synthesized in the central and peripheral nervous systems are termed neurosteroids. However, the biosynthetic pathways leading to the formation of neurosteroids are still incompletely elucidated. 7α-Hydroxypregnenolone, a novel bioactive neurosteroid stimulating locomot
- PMID 23685042
- Substrate-modulated cytochrome P450 17A1 and cytochrome b5 interactions revealed by NMR.
- Estrada DF1, Laurence JS, Scott EE.
- The Journal of biological chemistry.J Biol Chem.2013 Jun 7;288(23):17008-18. doi: 10.1074/jbc.M113.468926. Epub 2013 Apr 25.
- The membrane heme protein cytochrome b5 (b5) can enhance, inhibit, or have no effect on cytochrome P450 (P450) catalysis, depending on the specific P450, substrate, and reaction conditions, but the structural basis remains unclear. Here the interactions between the soluble domain of microsomal b5 an
- PMID 23620596
Related Links
- Structure, classification, information, physical and chemical properties for 17-Hydroxypregnenolone, 17alpha-Hydroxypregnenolone, 5-Pregnen-3beta,17alpha-diol-20-one, 17-Hydroxy-delta5-pregnenolone ... A 21-carbon steroid that is ...
- 17-alpha-Hydroxypregnenolone information including symptoms, causes, diseases, symptoms, treatments, and other medical and health issues. ... Introduction: 17-alpha-Hydroxypregnenolone Description of 17-alpha ...
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α、アルファ
- 関
- alfa