17a-Hydroxypregnenolone (BioDeep_00000005729)

 

Secondary id: BioDeep_00000174007, BioDeep_00000637522

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite


代谢物信息卡片


1-[(1S,2R,5S,10R,11S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethan-1-one

化学式: C21H32O3 (332.2351)
中文名称: 17α-羟基孕烯醇酮, 17-羟孕烯醇酮, 17alpha-羟基孕烯醇酮
谱图信息: 最多检出来源 Homo sapiens(plant) 5.51%

分子结构信息

SMILES: CC(=O)C1(CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C)O
InChI: InChI=1S/C21H32O3/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/h4,15-18,23-24H,5-12H2,1-3H3

描述信息

17a-Hydroxypregnenolone is a 21-carbon steroid that is converted from pregnenolone by cytochrome P450 17alpha hydroxylase/C17,20 lyase (CYP17, EC 1.14.99.9). 17a-Hydroxypregnenolone is an intermediate in the delta-5 pathway of biosynthesis of gonadal steroid hormones and the adrenal corticosteroids. The first, rate-limiting and hormonally regulated step in the biosynthesis of all steroid hormones is the conversion of cholesterol to pregnenolone. The conversion of cholesterol to pregnenolone is accomplished by the cleavage of the cholesterol side chain, catalyzed by a mitochondrial cytochrome P450 enzyme termed P450scc where scc designates Side Chain Cleavage. All steroid hormones are made from the pregnenolone produced by P450scc; thus, the presence or absence of each of the activities of CYP17 directs this pregnenolone towards its final metabolic pathway. While all cytochrome P450 enzymes can catalyze multiple reactions on a single active site, CYP17 is the only one described to date in which these multiple activities are differentially regulated by a physiologic process. 17a-Hydroxypregnenolone is converted to dehydroepiandrosterone by the 17,20 lyase activity of CYP17. The ratio of the 17,20 lyase to 17 alpha-hydroxylase activity of CYP17 determines the ratio of C21 to C19 steroids produced. This ratio is regulated post-translationally by at least three factors: the abundance of the electron-donating protein P450 oxidoreductase, the presence of cytochrome b5, and the serine phosphorylation of CYP17. (PMID: 12573809).
C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones
17a-Hydroxypregnenolone is a pregnane steroid. 17a-Hydroxypregnenolone is a prohormone in the formation of dehydroepiandrosterone (DHEA).

同义名列表

32 个代谢物同义名

1-[(1S,2R,5S,10R,11S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethan-1-one; 1-[(1S,2R,5S,10R,11S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethanone; 17-Hydroxypregnenolone, (3beta,13alpha,17alpha)-isomer; 17-Hydroxypregnenolone, (3beta,13alpha)-isomer; 17-Hydroxypregnenolone, (3beta,17alpha)-isomer; 17-Hydroxypregnenolone, (3alpha)-isomer; (3beta)-3,17-Dihydroxypregn-5-en-20-one; Pregn-5-ene-3alpha,17alpha-diol-20-one; (3b)-3,17-Dihydroxypregn-5-en-20-one; (3Β)-3,17-dihydroxypregn-5-en-20-one; 5-Pregnen-3beta,17alpha-diol-20-one; 3b,17-Dihydroxy-pregn-5-en-20-one; 3b,17a-Dihydroxypregn-5-en-20-one; 3b,17-Dihydroxy-5-pregnen-20-one; 3,17-Dihydroxypregn-5-en-20-one; 17-alpha-Hydroxypregnenolone; 5-Pregnen-3β,17α-diol-20-one; 17 alpha-Hydroxypregnenolone; 5-Pregnen-3b,17a-diol-20-one; 17 alpha Hydroxypregnenolone; 17alpha Hydroxypregnenolone; 17alpha-hydroxypregnenolone; 17alpha-Hydroxypregnanolone; 17-Hydroxy-D5-pregnenolone; 17a-Hydroxypregnenolone; 17-Hydroxypregnenolone; 17 Hydroxypregnenolone; 17a-Hydroxypregnolone; Hydroxypregnenolone; 17-OH-Pregnenolone; CID 440573; 17alpha-Hydroxypregnenolone



数据库引用编号

29 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(5)

BioCyc(1)

PlantCyc(0)

代谢反应

112 个相关的代谢反应过程信息。

Reactome(60)

BioCyc(3)

  • androgen biosynthesis: 17-α-hydroxypregnenolone + O2 + a reduced [NADPH-hemoprotein reductase] ⟶ 3-β-hydroxyandrost-5-en-17-one + H+ + H2O + acetate + an oxidized [NADPH-hemoprotein reductase]
  • androgen biosynthesis: NADP+ + testosterone ⟶ H+ + NADPH + androst-4-ene-3,17-dione
  • androgen biosynthesis: NAD+ + dehydroepiandrosterone ⟶ 5-androstene-3,17-dione + H+ + NADH

WikiPathways(3)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(46)

PharmGKB(0)

2 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。

亚细胞结构定位 关联基因列表
Cytoplasm 4 AR, HSD3B1, POMC, PRL
Peripheral membrane protein 3 CYP1B1, CYP21A2, HSD17B6
Endoplasmic reticulum membrane 6 CYP17A1, CYP19A1, CYP1B1, CYP21A2, HSD3B1, STAR
Nucleus 2 AR, PRL
cytosol 1 AR
nucleoplasm 2 AR, PRL
RNA polymerase II transcription regulator complex 1 PRL
Cell membrane 1 STAR
Early endosome membrane 1 HSD17B6
Multi-pass membrane protein 2 CYP19A1, MT-CYB
Synapse 1 CRH
Golgi apparatus 1 IGFBP1
Golgi membrane 1 INS
mitochondrial inner membrane 2 HSD3B1, MT-CYB
neuronal cell body 1 CYP17A1
plasma membrane 3 AR, REN, STAR
Membrane 6 AR, CYP19A1, CYP1B1, CYP21A2, MT-CYB, REN
axon 1 CYP17A1
Lumenal side 1 HSD17B6
endoplasmic reticulum 4 CYP17A1, CYP19A1, HSD17B6, HSD3B1
extracellular space 10 CGA, CRH, GNRH1, IGF1, IGFBP1, IL2, INS, POMC, PRL, REN
mitochondrion 4 BCO2, CYP1B1, MT-CYB, STAR
protein-containing complex 1 AR
intracellular membrane-bounded organelle 3 CYP1B1, HSD17B6, HSD3B1
Microsome membrane 5 CYP17A1, CYP19A1, CYP1B1, CYP21A2, HSD17B6
Single-pass type I membrane protein 1 STAR
Secreted 9 CGA, CRH, IGF1, IGFBP1, IL2, INS, POMC, PRL, REN
extracellular region 10 CGA, CRH, GNRH1, IGF1, IGFBP1, IL2, INS, POMC, PRL, REN
Single-pass membrane protein 1 CYP21A2
mitochondrial matrix 2 BCO2, STAR
varicosity 1 CRH
neuronal dense core vesicle lumen 1 CRH
perikaryon 1 CRH
nucleolus 1 HSD3B1
apical part of cell 1 REN
Mitochondrion inner membrane 1 MT-CYB
mitochondrial intermembrane space 2 HSD3B1, STAR
secretory granule 1 POMC
nuclear speck 1 AR
chromatin 2 AR, PRL
intercellular bridge 1 HSD3B1
endosome lumen 2 INS, PRL
Smooth endoplasmic reticulum membrane 1 HSD3B1
exocytic vesicle 1 IGF1
secretory granule lumen 2 INS, POMC
Golgi lumen 2 CGA, INS
endoplasmic reticulum lumen 2 IGFBP1, INS
platelet alpha granule lumen 1 IGF1
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
respiratory chain complex III 1 MT-CYB
follicle-stimulating hormone complex 1 CGA
pituitary gonadotropin complex 1 CGA
alphav-beta3 integrin-IGF-1-IGF1R complex 1 IGF1
insulin-like growth factor binding protein complex 1 IGF1
insulin-like growth factor ternary complex 1 IGF1


文献列表

  • V A Filatova, R V Rozhivanov, I Z Bondarenko, V A Ioutsi, E N Andreeva, G A Mel'nichenko, N G Mokrysheva. [Features of steroidogenesis and arterial hypertension in men in different types of "physiological" male hyperandrogenism]. Problemy endokrinologii. 2023 May; 69(2):80-91. doi: 10.14341/probl13226. [PMID: 37448275]
  • Johanna Ruhnau, Stephanie Hübner, Donna Sunny, Till Ittermann, Michaela F Hartmann, Jan De Lafollie, Stefan A Wudy, Matthias Heckmann. Impact of Gestational and Postmenstrual Age on Excretion of Fetal Zone Steroids in Preterm Infants Determined by Gas Chromatography-Mass Spectrometry. The Journal of clinical endocrinology and metabolism. 2021 08; 106(9):e3725-e3738. doi: 10.1210/clinem/dgab194. [PMID: 33822093]
  • Marco Mezzullo, Carla Pelusi, Alessia Fazzini, Andrea Repaci, Guido Di Dalmazi, Alessandra Gambineri, Uberto Pagotto, Flaminia Fanelli. Female and male serum reference intervals for challenging sex and precursor steroids by liquid chromatography - tandem mass spectrometry. The Journal of steroid biochemistry and molecular biology. 2020 03; 197(?):105538. doi: 10.1016/j.jsbmb.2019.105538. [PMID: 31734493]
  • Abdelmoneim Khashana, Hoda Ahmed, Amal Ahmed, Amina Abdelwahab, Timo Saarela, Mika Rämet, Mikko Hallman. Cortisol precursors in neonates with vasopressor-resistant hypotension in relationship to demographic characteristics. The journal of maternal-fetal & neonatal medicine : the official journal of the European Association of Perinatal Medicine, the Federation of Asia and Oceania Perinatal Societies, the International Society of Perinatal Obstetricians. 2018 Sep; 31(18):2473-2477. doi: 10.1080/14767058.2017.1344966. [PMID: 28629239]
  • Christopher M Jones, Ashwini Mallappa, Nicole Reisch, Nikolaos Nikolaou, Nils Krone, Beverly A Hughes, Donna M O'Neil, Martin J Whitaker, Jeremy W Tomlinson, Karl-Heinz Storbeck, Deborah P Merke, Richard J Ross, Wiebke Arlt. Modified-Release and Conventional Glucocorticoids and Diurnal Androgen Excretion in Congenital Adrenal Hyperplasia. The Journal of clinical endocrinology and metabolism. 2017 06; 102(6):1797-1806. doi: 10.1210/jc.2016-2855. [PMID: 27845856]
  • Patrizia Porcu, Todd K O'Buckley, Marcelo F Lopez, Howard C Becker, Michael F Miles, Robert W Williams, A Leslie Morrow. Initial genetic dissection of serum neuroactive steroids following chronic intermittent ethanol across BXD mouse strains. Alcohol (Fayetteville, N.Y.). 2017 Feb; 58(?):107-125. doi: 10.1016/j.alcohol.2016.07.011. [PMID: 27884493]
  • Changzhuan Shao, Yiming Ren, Zinan Wang, Chenzhe Kang, Hongke Jiang, Aiping Chi. Detection of Urine Metabolites in a Rat Model of Chronic Fatigue Syndrome before and after Exercise. BioMed research international. 2017; 2017(?):8182020. doi: 10.1155/2017/8182020. [PMID: 28421200]
  • Shin-Hye Kim, Ju-Yeon Moon, Hironobu Sasano, Man Ho Choi, Mi-Jung Park. Body Fat Mass Is Associated With Ratio of Steroid Metabolites Reflecting 17,20-Lyase Activity in Prepubertal Girls. The Journal of clinical endocrinology and metabolism. 2016 12; 101(12):4653-4660. doi: 10.1210/jc.2016-2515. [PMID: 27648966]
  • Juilee Rege, Shigehiro Karashima, Antonio M Lerario, Joshua M Smith, Richard J Auchus, Josephine Z Kasa-Vubu, Hironobu Sasano, Yasuhiro Nakamura, Perrin C White, William E Rainey. Age-dependent Increases in Adrenal Cytochrome b5 and Serum 5-Androstenediol-3-sulfate. The Journal of clinical endocrinology and metabolism. 2016 12; 101(12):4585-4593. doi: 10.1210/jc.2016-2864. [PMID: 27623070]
  • Antonín Pařízek, Martin Hill, Michaela Dušková, Libor Vítek, Marta Velíková, Radmila Kancheva, Patrik Šimják, Michal Koucký, Zuzana Kokrdová, Karolína Adamcová, Andrej Černý, Zdeněk Hájek, Luboslav Stárka. A Comprehensive Evaluation of Steroid Metabolism in Women with Intrahepatic Cholestasis of Pregnancy. PloS one. 2016; 11(8):e0159203. doi: 10.1371/journal.pone.0159203. [PMID: 27494119]
  • Yuanxiang Jin, Xiaojian Lin, Wenyu Miao, Linggang Wang, Yan Wu, Zhengwei Fu. Oral exposure of pubertal male mice to endocrine-disrupting chemicals alters fat metabolism in adult livers. Environmental toxicology. 2015 Dec; 30(12):1434-44. doi: 10.1002/tox.22013. [PMID: 24916741]
  • Ariadni Spyroglou, Anna Riester, Katharina Mueller-Peltzer, Ailing Lu, Juliane Rohde, Constanze Hantel, Claudia Kuehne, Alexandra Kulle, Felix Riepe, Jan M Deussing, Felix Beuschlein. Adrenal and Ovarian Phenotype of a Tissue-Specific Urocortin 2-Overexpressing Mouse Model. Endocrinology. 2015 Jul; 156(7):2646-56. doi: 10.1210/en.2014-1971. [PMID: 25942073]
  • Vitor Guilherme Brito de Araújo, Renata Santarem de Oliveira, Kallianna Paula Duarte Gameleira, Cátia Barbosa Cruz, Adriana Lofrano-Porto. 3β-hydroxysteroid dehydrogenase type II deficiency on newborn screening test. Arquivos brasileiros de endocrinologia e metabologia. 2014 Aug; 58(6):650-5. doi: 10.1590/0004-2730000003098. [PMID: 25211449]
  • Hyun Suk Shin, Hamid R Habibi, Cheol Young Choi. The environmental regulation of maturation in goldfish, Carassius auratus: effects of various LED light spectra. Comparative biochemistry and physiology. Part A, Molecular & integrative physiology. 2014 Feb; 168(?):17-24. doi: 10.1016/j.cbpa.2013.11.003. [PMID: 24239668]
  • Na Na Kim, Hyun Suk Shin, Young Jae Choi, Cheol Young Choi. Kisspeptin regulates the hypothalamus-pituitary-gonad axis gene expression during sexual maturation in the cinnamon clownfish, Amphiprion melanopus. Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology. 2014 Feb; 168(?):19-32. doi: 10.1016/j.cbpb.2013.11.002. [PMID: 24239680]
  • D Kariyawasam, A Simon, K Laborde, S Parat, P-F Souchon, P Frange, S Blanche, M Polak. Adrenal enzyme impairment in neonates and adolescents treated with ritonavir and protease inhibitors for HIV exposure or infection. Hormone research in paediatrics. 2014; 81(4):226-31. doi: 10.1159/000356916. [PMID: 24577112]
  • Amir Kalani, Gul Bahtiyar, Alan Sacerdote. Ashwagandha root in the treatment of non-classical adrenal hyperplasia. BMJ case reports. 2012 Sep; 2012(?):. doi: 10.1136/bcr-2012-006989. [PMID: 22987912]
  • Shogo Haraguchi, Teppei Koyama, Itaru Hasunuma, Shin-ichiro Okuyama, Takayoshi Ubuka, Sakae Kikuyama, Jean-Luc Do Rego, Hubert Vaudry, Kazuyoshi Tsutsui. Acute stress increases the synthesis of 7α-hydroxypregnenolone, a new key neurosteroid stimulating locomotor activity, through corticosterone action in newts. Endocrinology. 2012 Feb; 153(2):794-805. doi: 10.1210/en.2011-1422. [PMID: 22128027]
  • Martin Hill, Jana Vrbíková, Jana Zárubová, Radmila Kancheva, Marta Velíková, Lyudmila Kancheva, Jana Kubátová, Michaela Dušková, Petr Marusič, Antonín Pařízek, Luboslav Stárka. The steroid metabolome in lamotrigine-treated women with epilepsy. Steroids. 2011 Nov; 76(12):1351-7. doi: 10.1016/j.steroids.2011.07.002. [PMID: 21787799]
  • Cheng Wang, Rennan Feng, Dianjun Sun, Ying Li, Xinxin Bi, Changhao Sun. Metabolic profiling of urine in young obese men using ultra performance liquid chromatography and Q-TOF mass spectrometry (UPLC/Q-TOF MS). Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2011 Oct; 879(27):2871-6. doi: 10.1016/j.jchromb.2011.08.014. [PMID: 21890434]
  • Ryuji Kouyama, Kiichiro Hiraishi, Toru Sugiyama, Hajime Izumiyama, Takanobu Yoshimoto, Takumi Akashi, Kazunori Kihara, Keiko Homma, Hirotaka Shibata, Yukio Hirata. Clinicopathological features, biochemical and molecular markers in 5 patients with adrenocortical carcinoma. Endocrine journal. 2011; 58(7):527-34. doi: 10.1507/endocrj.k11e-026. [PMID: 21521927]
  • Päivi Nykänen, Kirsti Heinonen, Felix G Riepe, Wolfgang G Sippell, Raimo Voutilainen. Serum concentrations of adrenal steroids and their precursors as a measure of maturity of adrenocortical function in very premature newborns. Hormone research in paediatrics. 2010; 74(5):358-64. doi: 10.1159/000314970. [PMID: 20606393]
  • Marie-Claude Villeneuve, Richard E Ostlund, Jean-Patrice Baillargeon. Hyperinsulinemia is closely related to low urinary clearance of D-chiro-inositol in men with a wide range of insulin sensitivity. Metabolism: clinical and experimental. 2009 Jan; 58(1):62-8. doi: 10.1016/j.metabol.2008.08.007. [PMID: 19059532]
  • Helena Vceláková, Martin Hill, Oldrich Lapcík, Antonín Parízek. Determination of 17alpha-hydroxypregnenolone sulfate and its application in diagnostics. Steroids. 2007 Apr; 72(4):323-7. doi: 10.1016/j.steroids.2006.11.026. [PMID: 17298837]
  • H Budzinski, M H Devier, P Labadie, A Togola. Analysis of hormonal steroids in fish plasma and bile by coupling solid-phase extraction to GC/MS. Analytical and bioanalytical chemistry. 2006 Nov; 386(5):1429-39. doi: 10.1007/s00216-006-0686-9. [PMID: 16906384]
  • Mark M Kushnir, Alan L Rockwood, William L Roberts, Elizabeth G Pattison, William E Owen, Ashley M Bunker, A Wayne Meikle. Development and performance evaluation of a tandem mass spectrometry assay for 4 adrenal steroids. Clinical chemistry. 2006 Aug; 52(8):1559-67. doi: 10.1373/clinchem.2006.068445. [PMID: 16777916]
  • N S Sieber-Ruckstuhl, F S Boretti, M Wenger, C Maser-Gluth, C E Reusch. Cortisol, aldosterone, cortisol precursor, androgen and endogenous ACTH concentrations in dogs with pituitary-dependant hyperadrenocorticism treated with trilostane. Domestic animal endocrinology. 2006 Jul; 31(1):63-75. doi: 10.1016/j.domaniend.2005.09.004. [PMID: 16233969]
  • Noriko Tagawa, Masanao Katagiri, Yoshiharu Kobayashi. Developmental changes of serum steroids produced by cytochrome P450c17 in rat. Steroids. 2006 Feb; 71(2):165-70. doi: 10.1016/j.steroids.2005.09.006. [PMID: 16280146]
  • Rainer H Straub, Peter Härle, Martin Kriegel, Jürgen Schölmerich, Hanns-Martin Lorenz. Adrenal and gonadal hormone variations during a febrile attack in a woman with tumor necrosis factor receptor-associated periodic syndrome. The Journal of clinical endocrinology and metabolism. 2005 Oct; 90(10):5884-7. doi: 10.1210/jc.2005-1016. [PMID: 16030167]
  • Martin Hill, Petr Popov, Helena Havlíková, Lyudmila Kancheva, Jana Vrbíková, Radmila Kancheva, Vladimír Pouzar, Ivan Cerný, Luboslav Stárka. Altered profiles of serum neuroactive steroids in premenopausal women treated for alcohol addiction. Steroids. 2005 Jul; 70(8):515-24. doi: 10.1016/j.steroids.2005.02.013. [PMID: 15894035]
  • Livia M Mermejo, Lucila L K Elias, S Marui, Ayrton C Moreira, Berenice B Mendonca, Margaret de Castro. Refining hormonal diagnosis of type II 3beta-hydroxysteroid dehydrogenase deficiency in patients with premature pubarche and hirsutism based on HSD3B2 genotyping. The Journal of clinical endocrinology and metabolism. 2005 Mar; 90(3):1287-93. doi: 10.1210/jc.2004-1552. [PMID: 15585552]
  • Marie Bicíková, Daniela Rípová, Martin Hill, Roman Jirák, Helena Havlíková, Jaroslava Tallová, Richard Hampl. Plasma levels of 7-hydroxylated dehydroepiandrosterone (DHEA) metabolites and selected amino-thiols as discriminatory tools of Alzheimer's disease and vascular dementia. Clinical chemistry and laboratory medicine. 2004 May; 42(5):518-24. doi: 10.1515/cclm.2004.088. [PMID: 15202788]
  • Diane Thiboutot, Sami Jabara, Jan M McAllister, Aruntha Sivarajah, Kathyrn Gilliland, Zhaoyuan Cong, Gary Clawson. Human skin is a steroidogenic tissue: steroidogenic enzymes and cofactors are expressed in epidermis, normal sebocytes, and an immortalized sebocyte cell line (SEB-1). The Journal of investigative dermatology. 2003 Jun; 120(6):905-14. doi: 10.1046/j.1523-1747.2003.12244.x. [PMID: 12787114]
  • Daniela Vogl, Werner Falk, Monika Dorner, Jürgen Schölmerich, Rainer H Straub. Serum levels of pregnenolone and 17-hydroxypregnenolone in patients with rheumatoid arthritis and systemic lupus erythematosus: relation to other adrenal hormones. The Journal of rheumatology. 2003 Feb; 30(2):269-75. doi: . [PMID: 12563679]
  • Noriko Tagawa, Mitsuhiro Ohta, Naoto Nakamura, Koji Nakano, Hiroshi Obayashi, Yoshiharu Kobayashi. Serum concentrations of delta 5-3 beta-hydroxysteroids in type 2 diabetes mellitus. Biological & pharmaceutical bulletin. 2002 Dec; 25(12):1634-8. doi: 10.1248/bpb.25.1634. [PMID: 12499654]
  • Felix G Riepe, Philip Mahler, Wolfgang G Sippell, Carl-Joachim Partsch. 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 and metabolism. 2002 Sep; 87(9):4301-6. doi: 10.1210/jc.2002-020452. [PMID: 12213889]
  • Stefan A Wudy, Michaela Hartmann, Janos Homoki. Determination of 11-deoxycortisol (Reichstein's compound S) in human plasma by clinical isotope dilution mass spectrometry using benchtop gas chromatography-mass selective detection. Steroids. 2002 Sep; 67(10):851-7. doi: 10.1016/s0039-128x(02)00052-1. [PMID: 12231120]
  • J Vrbíková, M Bicíková, J Tallová, M Hill, L Stárka. Homocysteine and steroids levels in metformin treated women with polycystic ovary syndrome. Experimental and clinical endocrinology & diabetes : official journal, German Society of Endocrinology [and] German Diabetes Association. 2002 Apr; 110(2):74-6. doi: 10.1055/s-2002-23489. [PMID: 11928069]
  • F G Riepe, S Wonka, C J Partsch, W G Sippell. Automated chromatographic system for the simultaneous measurement of plasma pregnenolone and 17-hydroxypregnenolone by radioimmunoassay. Journal of chromatography. B, Biomedical sciences and applications. 2001 Nov; 763(1-2):99-106. doi: 10.1016/s0378-4347(01)00373-5. [PMID: 11710589]
  • S A Wudy, M Hartmann, C Solleder, J Homoki. Determination of 17alpha-hydroxypregnenolone in human plasma by routine isotope dilution mass spectrometry using benchtop gas chromatography-mass selective detection. Steroids. 2001 Oct; 66(10):759-62. doi: 10.1016/s0039-128x(01)00109-x. [PMID: 11522338]
  • M R Palmert, D L Hayden, M J Mansfield, J F Crigler, W F Crowley, D W Chandler, P A Boepple. The longitudinal study of adrenal maturation during gonadal suppression: evidence that adrenarche is a gradual process. The Journal of clinical endocrinology and metabolism. 2001 Sep; 86(9):4536-42. doi: 10.1210/jcem.86.9.7863. [PMID: 11549704]
  • A D Genazzani, C Bersi, S Luisi, F Fruzzetti, B Malavasi, M Luisi, F Petraglia, A R Genazzani. Increased adrenal steroid secretion in response to CRF in women with hypothalamic amenorrhea. The Journal of steroid biochemistry and molecular biology. 2001 Sep; 78(3):247-52. doi: 10.1016/s0960-0760(01)00094-2. [PMID: 11595505]
  • J Fiet, F Giton, A Boudi, P Boudou, H Soliman, J Villette, H Galons. Plasma 17-OH pregnenolone: comparison of a time-resolved fluoroimmunoassay using a new tracer 17-OH pregnenolone-3-oxyacetyl-biotine with a radioimmunoassay using 125I 17-OH pregnenolone-3-hemisuccinate-histamine. Steroids. 2001 Feb; 66(2):81-6. doi: 10.1016/s0039-128x(00)00207-5. [PMID: 11146086]
  • M Bicíková, J Tallová, M Hill, Z Krausová, R Hampl. Serum concentrations of some neuroactive steroids in women suffering from mixed anxiety-depressive disorder. Neurochemical research. 2000 Dec; 25(12):1623-7. doi: 10.1023/a:1026622704704. [PMID: 11152391]
  • R Huerta, D Dewailly, C Decanter, E S Knochenhauer, L R Boots, R Azziz. Adrenocortical hyperresponsivity to adrenocorticotropic hormone: a mechanism favoring the normal production of cortisol in 21-hydroxylase-deficient nonclassic adrenal hyperplasia. Fertility and sterility. 2000 Aug; 74(2):329-34. doi: 10.1016/s0015-0282(00)00631-2. [PMID: 10927053]
  • P Soucy, V Luu-The. Conversion of pregnenolone to DHEA by human 17alpha-hydroxylase/17, 20-lyase (P450c17). Evidence that DHEA is produced from the released intermediate, 17alpha-hydroxypregnenolone. European journal of biochemistry. 2000 Jun; 267(11):3243-7. doi: 10.1046/j.1432-1327.2000.01349.x. [PMID: 10824109]
  • S Marui, M Castro, A C Latronico, L L Elias, I J Arnhold, A C Moreira, B B Mendonca. Mutations in the type II 3beta-hydroxysteroid dehydrogenase (HSD3B2) gene can cause premature pubarche in girls. Clinical endocrinology. 2000 Jan; 52(1):67-75. doi: 10.1046/j.1365-2265.2000.00873.x. [PMID: 10651755]
  • J L Sadoul, B Kézachian, S Altare, Y Hadjali, B Canivet. Apparent activities of 21-hydroxylase, 17alpha-hydroxylase and 17,20-lyase are impaired in adrenal incidentalomas. European journal of endocrinology. 1999 Sep; 141(3):238-45. doi: 10.1530/eje.0.1410238. [PMID: 10474121]
  • M Hill, R Hampl, D Lukác, O Lapcík, V Pouzar, J Sulcová. Elimination of cross-reactivity by addition of an excess of cross-reactant for radioimmunoassay of 17alpha-hydroxypregnenolone. Steroids. 1999 May; 64(5):341-55. doi: 10.1016/s0039-128x(99)00017-3. [PMID: 10406484]
  • M Hill, D Lukác, O Lapcík, J Sulcová, R Hampl, V Pouzar, L Stárka. Age relationships and sex differences in serum levels of pregnenolone and 17-hydroxypregnenolone in healthy subjects. Clinical chemistry and laboratory medicine. 1999 Apr; 37(4):439-47. doi: 10.1515/cclm.1999.072. [PMID: 10369116]
  • T Imai, J Tobinaga, T Morita-Matsuyama, T Kikumori, H Sasano, H Seo, H Funahashi. Virilizing adrenocortical adenoma: in vitro steroidogenesis, immunohistochemical studies of steroidogenic enzymes, and gene expression of corticotropin receptor. Surgery. 1999 Apr; 125(4):396-402. doi: 10.1016/s0039-6060(99)70007-3. [PMID: 10216530]
  • J L Ponthier, C H Shackleton, J M Trant. Seasonal changes in the production of two novel and abundant ovarian steroids in the channel catfish (Ictalurus punctatus). General and comparative endocrinology. 1998 Aug; 111(2):141-55. doi: 10.1006/gcen.1998.7096. [PMID: 9679086]
  • S A Mathias, O P Mgbonyebi, E Motley, J R Owens, J J Mrotek. Modulation of adrenal cell functions by cadmium salts. 4. Ca(2+)-dependent sites affected by CdCl2 during basal and ACTH-stimulated steroid synthesis. Cell biology and toxicology. 1998 Jun; 14(3):225-36. doi: 10.1023/a:1007422928427. [PMID: 9689495]
  • I Salinas Vert, L Audí Parera, M L Granada Ybern, A Lucas Martín, E Pizarro Lozano, M Foz Sala, A Sanmartí Sala. [Defects of adrenal steroidogenesis in patients with hirsutism]. Medicina clinica. 1998 Feb; 110(5):171-6. doi: . [PMID: 9547720]
  • N Tagawa, S Kusuda, Y Kobayashi. C16 hydroxylation of 3beta-hydroxy-delta5-steroids during the early neonatal period. Biological & pharmaceutical bulletin. 1997 Dec; 20(12):1295-9. doi: 10.1248/bpb.20.1295. [PMID: 9448107]
  • L Ibáñez, N Potau, M Zampolli, M E Street, A Carrascosa. Girls diagnosed with premature pubarche show an exaggerated ovarian androgen synthesis from the early stages of puberty: evidence from gonadotropin-releasing hormone agonist testing. Fertility and sterility. 1997 May; 67(5):849-55. doi: 10.1016/s0015-0282(97)81396-9. [PMID: 9130889]
  • P Moghetti, R Castello, C Negri, F Tosi, G G Spiazzi, E Brun, R Balducci, V Toscano, M Muggeo. Insulin infusion amplifies 17 alpha-hydroxycorticosteroid intermediates response to adrenocorticotropin in hyperandrogenic women: apparent relative impairment of 17,20-lyase activity. The Journal of clinical endocrinology and metabolism. 1996 Mar; 81(3):881-6. doi: 10.1210/jcem.81.3.8772544. [PMID: 8772544]
  • L Ghizzoni, R Virdis, A Vottero, M Cappa, M E Street, M Zampolli, L Ibañez, S Bernasconi. Pituitary-ovarian responses to leuprolide acetate testing in patients with congenital adrenal hyperplasia due to 21-hydroxylase deficiency. The Journal of clinical endocrinology and metabolism. 1996 Feb; 81(2):601-6. doi: 10.1210/jcem.81.2.8636275. [PMID: 8636275]
  • L Lazar, R Kauli, C Bruchis, J Nordenberg, A Galatzer, A Pertzelan. High prevalence of abnormal adrenal response in girls with central precocious puberty at early pubertal stages. European journal of endocrinology. 1995 Oct; 133(4):407-11. doi: 10.1530/eje.0.1330407. [PMID: 7581962]
  • M Rieu, Y Reznik, J M Vannetzel, J Mahoudeau, J L Berrod, J M Kuhn. Testicular steroidogenesis in adult men with human chorionic gonadotropin-producing tumors. The Journal of clinical endocrinology and metabolism. 1995 Aug; 80(8):2404-9. doi: 10.1210/jcem.80.8.7629236. [PMID: 7629236]
  • N P Goncharov, G S Kolesnikova, V I Vorontsov, L Ia Rozhinskaia, E I Marova. [Steroidogenesis in patients with various adrenal and gonadal dysfunctions]. Vestnik Rossiiskoi akademii meditsinskikh nauk. 1995; ?(6):30-7. doi: . [PMID: 7626995]
  • J Sólyom. Identification of enzyme deficiencies resulting in congenital adrenal hyperplasia. Acta bio-medica de L'Ateneo parmense : organo della Societa di medicina e scienze naturali di Parma. 1995; 66(3-4):99-104. doi: NULL. [PMID: 8578942]
  • J Fiet, J P Gosling, H Soliman, H Galons, P Boudou, P Aubin, A Belanger, J M Villette, R Julien, J L Brérault. Hirsutism and acne in women: coordinated radioimmunoassays for eight relevant plasma steroids. Clinical chemistry. 1994 Dec; 40(12):2296-305. doi: . [PMID: 7988017]
  • R L Rosenfield, R B Barnes, D A Ehrmann. Studies of the nature of 17-hydroxyprogesterone hyperresonsiveness to gonadotropin-releasing hormone agonist challenge in functional ovarian hyperandrogenism. The Journal of clinical endocrinology and metabolism. 1994 Dec; 79(6):1686-92. doi: 10.1210/jcem.79.6.7989476. [PMID: 7989476]
  • R Balducci, B Boscherini, A Mangiantini, M Morellini, V Toscano. Isolated precocious pubarche: an approach. The Journal of clinical endocrinology and metabolism. 1994 Aug; 79(2):582-9. doi: 10.1210/jcem.79.2.8045980. [PMID: 8045980]
  • J L Gachancard-Bouya, R J Bègue. Urinary steroids from a newborn human infant. Identification of 2 alpha-hydroxy-4-pregnene-3,20-dione, 3 beta,15 beta-dihydroxy-5-pregnen-20-one and 3 beta,15 alpha-dihydroxy-5-pregnen-20-one. The Journal of steroid biochemistry and molecular biology. 1994 Jun; 49(2-3):213-26. doi: 10.1016/0960-0760(94)90013-2. [PMID: 8031719]
  • F A Conte, M M Grumbach, Y Ito, C R Fisher, E R Simpson. A syndrome of female pseudohermaphrodism, hypergonadotropic hypogonadism, and multicystic ovaries associated with missense mutations in the gene encoding aromatase (P450arom). The Journal of clinical endocrinology and metabolism. 1994 Jun; 78(6):1287-92. doi: 10.1210/jcem.78.6.8200927. [PMID: 8200927]
  • S Yonezawa, A Kambegawa, S Tokudome. Covalent coupling of a steroid to microwell plates for use in a competitive enzyme-linked immunosorbent assay. Journal of immunological methods. 1993 Nov; 166(1):55-61. doi: 10.1016/0022-1759(93)90328-5. [PMID: 8228288]
  • R Azziz, E L Bradley, H D Potter, L R Boots. 3 beta-hydroxysteroid dehydrogenase deficiency in hyperandrogenism. American journal of obstetrics and gynecology. 1993 Mar; 168(3 Pt 1):889-95. doi: 10.1016/s0002-9378(12)90840-6. [PMID: 8456898]
  • T Akamatsu, H Chiba, H Kamiyama, K Hirose, H Saito, T Yanaihara. Menopause related changes of adrenocortical steroid production. Asia-Oceania journal of obstetrics and gynaecology. 1992 Sep; 18(3):271-6. doi: 10.1111/j.1447-0756.1992.tb00013.x. [PMID: 1333183]
  • W Futterweit, G Green, N Tarlin, A Dunaif. Chronic high-dosage androgen administration to ovulatory women does not alter adrenocortical steroidogenesis. Fertility and sterility. 1992 Jul; 58(1):124-8. doi: NULL. [PMID: 1320574]
  • J E Nestler, M A McClanahan, J N Clore, W G Blackard. Insulin inhibits adrenal 17,20-lyase activity in man. The Journal of clinical endocrinology and metabolism. 1992 Feb; 74(2):362-7. doi: 10.1210/jcem.74.2.1730815. [PMID: 1730815]
  • J Homoki, J Sólyom, U Wachter, W M Teller. Urinary excretion of 17-hydroxypregnanolones in patients with different forms of congenital adrenal hyperplasia due to steroid 21-hydroxylase deficiency. European journal of pediatrics. 1992 Jan; 151(1):24-8. doi: 10.1007/bf02073884. [PMID: 1728539]
  • Y Nishi, T Tezuka. Mild adrenal 3 beta-hydroxysteroid dehydrogenase deficiency in children with accelerated growth, premature pubarche and/or hirsutism. European journal of pediatrics. 1992 Jan; 151(1):19-23. doi: 10.1007/bf02073883. [PMID: 1309452]
  • R Azziz, F L Gay, S R Potter, E Bradley, L R Boots. The effects of prolonged hypertestosteronemia on adrenocortical biosynthesis in oophorectomized women. The Journal of clinical endocrinology and metabolism. 1991 May; 72(5):1025-30. doi: 10.1210/jcem-72-5-1025. [PMID: 1850751]
  • P Luppa, R Munker, D Nagel, M Weber, D Engelhardt. Serum androgens in intensive-care patients: correlations with clinical findings. Clinical endocrinology. 1991 Apr; 34(4):305-10. doi: 10.1111/j.1365-2265.1991.tb03771.x. [PMID: 1831739]
  • K Grunwald, T Rabe, J Urbancsek, B Runnebaum, P Vecsei. Normal values for a short-time ACTH intravenous and intramuscular stimulation test in women in the reproductive age. Gynecological endocrinology : the official journal of the International Society of Gynecological Endocrinology. 1990 Dec; 4(4):287-306. doi: 10.3109/09513599009024983. [PMID: 1964539]
  • K Hirato, T Yanaihara. Serum steroid hormone levels in neonates born from the mother with placental sulfatase deficiency. Endocrinologia japonica. 1990 Oct; 37(5):731-9. doi: 10.1507/endocrj1954.37.731. [PMID: 2150812]
  • Y Nishi. Nonclassical 3 beta-hydroxysteroid dehydrogenase deficiency in young girls with hirsutism and premature pubarche. Endocrinologia japonica. 1990 Oct; 37(5):763-7. doi: 10.1507/endocrj1954.37.763. [PMID: 2150813]
  • S Nakamura, N Kuzuya, Y Koide, M Matsumara, Y Watanabe, H Tomizawa, Y Murayama, Y Okuda, Y Takuwa, M Itakura. Successful treatment of a metastatic hormone-producing adrenal cancer by a combination of mitotane, tegafur and surgical resection. Endocrinologia japonica. 1990 Oct; 37(5):753-62. doi: 10.1507/endocrj1954.37.753. [PMID: 2086205]
  • S F Siegel, D N Finegold, R Lanes, P A Lee. ACTH stimulation tests and plasma dehydroepiandrosterone sulfate levels in women with hirsutism. The New England journal of medicine. 1990 Sep; 323(13):849-54. doi: 10.1056/nejm199009273231301. [PMID: 2168515]
  • M C Lorence, B A Murry, J M Trant, J I Mason. Human 3 beta-hydroxysteroid dehydrogenase/delta 5----4isomerase from placenta: expression in nonsteroidogenic cells of a protein that catalyzes the dehydrogenation/isomerization of C21 and C19 steroids. Endocrinology. 1990 May; 126(5):2493-8. doi: 10.1210/endo-126-5-2493. [PMID: 2139411]
  • M M Lee, L Rajagopalan, G J Berg, T Moshang. Serum adrenal steroid concentrations in premature infants. The Journal of clinical endocrinology and metabolism. 1989 Dec; 69(6):1133-6. doi: 10.1210/jcem-69-6-1133. [PMID: 2531155]
  • A H Morris, E O Reiter, M E Geffner, B M Lippe, R M Itami, D M Mayes. Absence of nonclassical congenital adrenal hyperplasia in patients with precocious adrenarche. The Journal of clinical endocrinology and metabolism. 1989 Oct; 69(4):709-15. doi: 10.1210/jcem-69-4-709. [PMID: 2550505]
  • A Hurwitz, N Laufer, Z Palti, J B Schenker, P Vecsei, A Rösler. In-vitro steroid production by human granulosa lutein cells in long-term cultures. Gynecological endocrinology : the official journal of the International Society of Gynecological Endocrinology. 1989 Sep; 3(3):203-11. doi: 10.3109/09513598909152301. [PMID: 2531534]
  • W M Hague, J W Honour, J Adams, P Vecsei, H S Jacobs. Steroid responses to ACTH in women with polycystic ovaries. Clinical endocrinology. 1989 Apr; 30(4):355-65. doi: 10.1111/j.1365-2265.1989.tb00433.x. [PMID: 2532082]
  • K Nahoul, C Perrin, P Leymarie, J C Job. [Elevated levels of plasma 4-ene steroids in a case of congenital deficiency of 3 beta-hydroxysteroid dehydrogenase]. Annales d'endocrinologie. 1989; 50(1):58-63. doi: NULL. [PMID: 2524988]
  • K Shimozawa, S Saisho, J Yata, A Kambegawa. Age-related changes in serum 17-hydroxypregnenolone and 17-hydroxypregnenolone sulfate concentrations in human infancy and childhood. Endocrinologia japonica. 1988 Apr; 35(2):189-95. doi: 10.1507/endocrj1954.35.189. [PMID: 3208699]
  • K Shimozawa, S Saisho, J Yata, A Kambegawa. Serum 17-hydroxypregnenolone and 17-hydroxypregnenolone sulfate concentrations in patients with congenital adrenal hyperplasia due to 21-hydroxylase deficiency. Endocrinologia japonica. 1988 Feb; 35(1):11-8. doi: 10.1507/endocrj1954.35.11. [PMID: 3260857]
  • M Vermesh, P D Silva, G F Rosen, A G Vijod, R A Lobo. Effect of androgen on adrenal steroidogenesis in normal women. The Journal of clinical endocrinology and metabolism. 1988 Jan; 66(1):128-30. doi: 10.1210/jcem-66-1-128. [PMID: 2826523]
  • A Guerami, M W Varner, C H Shackleton, P C MacDonald, M L Casey. Origin of deoxycorticosterone and deoxycorticosterone sulfate in human pregnancy: absence of steroid 21-sulfatase activity in sulfatase-deficient placenta. Journal of steroid biochemistry. 1988 Jan; 29(1):57-62. doi: 10.1016/0022-4731(88)90376-7. [PMID: 3347051]
  • I Matsumura, M Hashino, S Maruyama, T Yanaihara, T Nakayama. [Relation between size of fetal and neonatal adrenal glands and steroid levels in maternal and neonatal serum]. Nihon Sanka Fujinka Gakkai zasshi. 1987 Dec; 39(12):2125-32. doi: NULL. [PMID: 2963083]
  • C H Shackleton, J Homoki, N F Taylor. A paradox: elevated 21-hydroxypregnenolone production in newborns with 21-hydroxylase deficiency. Steroids. 1987 Apr; 49(4-5):295-311. doi: 10.1016/0039-128x(87)90006-7. [PMID: 3502660]
  • L Dehennin, K Nahoul, R Scholler. Steroid 21-hydroxylation by human preovulatory follicles from stimulated cycles: a mass spectrometrical study of deoxycorticosterone, 21-hydroxypregnenolone and 11-deoxycortisol in follicular fluid. Journal of steroid biochemistry. 1987 Mar; 26(3):337-43. doi: 10.1016/0022-4731(87)90098-7. [PMID: 3495701]
  • K Makino, K Yasuda, M Okuyama, M Ojima, N Sasano, K Miura. An adrenocortical tumor secreting weak mineralocorticoids. Endocrinologia japonica. 1987 Feb; 34(1):65-72. doi: 10.1507/endocrj1954.34.65. [PMID: 3608914]
  • N Yamakita, K Yasuda, H Murase, M Murayama, E Goshima, M Hirai, N Noritake, N Takeda, K Miura. Response of plasma adrenal steroids to synthetic ACTH under ketoconazole in man. Endocrinologia japonica. 1987 Feb; 34(1):29-35. doi: 10.1507/endocrj1954.34.29. [PMID: 3038504]
  • T Maki. [Age-related changes in secretion of adrenocortical steroid hormones in normal healthy men]. Nihon Naibunpi Gakkai zasshi. 1986 May; 62(5):672-82. doi: 10.1507/endocrine1927.62.5_672. [PMID: 3015696]
  • S Maruyama, T Suzuki, T Yanaihara, H Araki, T Nakayawa. [C21-steroid profiles in pregnancy associated with intrauterine growth retardation]. Nihon Sanka Fujinka Gakkai zasshi. 1986 Apr; 38(4):513-9. doi: . [PMID: 3701142]
  • K Shimozawa, S Saisho, J Yata, A Kambegawa. [Age-related changes of serum 17 alpha-hydroxypregnenolone and 17 alpha-hydroxypregnenolone sulfate concentrations in infancy and childhood]. Nihon Naibunpi Gakkai zasshi. 1985 Aug; 61(8):785-93. doi: 10.1507/endocrine1927.61.8_785. [PMID: 4076471]