tetrahydrocortisol

Tetrahydrocortisol
Names
	IUPAC name 2-hydroxy-1-[(3R,5R,8S,9S,10S,11S,13S,14S,17R)-3,11,17-trihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-yl]ethanone
	Other names Urocortisol
Identifiers
CAS Registry Number	53-02-1
ChEBI	CHEBI:28320
ChemSpider	5655
	InChI InChI=1S/C21H34O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h12-16,18,22-24,26H,3-11H2,1-2H3/t12-,13-,14+,15+,16+,18-,19+,20+,21+/m1/s1 ; Key: AODPIQQILQLWGS-GXBDJPPSSA-N ; InChI=1/C21H34O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h12-16,18,22-24,26H,3-11H2,1-2H3/t12-,13-,14+,15+,16+,18-,19+,20+,21+/m1/s1; Key: AODPIQQILQLWGS-GXBDJPPSBG ;
Jmol-3D images	Image
PubChem	5864
	SMILES O=C(CO)[C@@]4(O)CC[C@H]3[C@H]2[C@@H]([C@@]1([C@@H](C[C@H](O)CC1)CC2)C)[C@@H](O)C[C@@]34C ;
Properties
Chemical formula	C21H34O5
Molar mass	366.49 g/mol
	Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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	Infobox references

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/04/18 11:11:45」(JST)

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Metabolite profiling and pharmacokinetic evaluation of hydrocortisone in a perfused three-dimensional human liver bioreactor.

Sarkar U1, Rivera-Burgos D1, Large EM1, Hughes DJ1, Ravindra KC1, Dyer RL1, Ebrahimkhani MR1, Wishnok JS2, Griffith LG1, Tannenbaum SR2.
Drug metabolism and disposition: the biological fate of chemicals.Drug Metab Dispos.2015 Jul;43(7):1091-9. doi: 10.1124/dmd.115.063495. Epub 2015 Apr 29.
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PMID 25926431

Apparent Mineralocorticoid Excess by a novel mutation and epigenetic modulation by HSD11B2 promoter methylation.

Pizzolo F1, Friso S1, Morandini F1, Antoniazzi F2, Zaltron C1, Udali S1, Gandini A2, Cavarzere P2, Salvagno G3, Giorgetti A4, Speziali G4, Choi SW5,6, Olivieri O1.
The Journal of clinical endocrinology and metabolism.J Clin Endocrinol Metab.2015 Jun 30:jc20151760. [Epub ahead of print]
CONTEXT: Apparent Mineralocorticoid Excess (AME) is a rare autosomal recessive disease resulting from mutations within the hydroxysteroid(11-beta)dehydrogenase2 (HSD11B2) gene causing a prominent mineralocorticoid receptor activation by cortisol, and hypokalemic low renin hypertension as the main cl
PMID 26126204

A simple LC-MS/MS method for the determination of cortisol, cortisone and tetrahydro-metabolites in human urine: assay development, validation and application in depression patients.

Zhai X1, Chen F1, Zhu C1, Lu Y2.
Journal of pharmaceutical and biomedical analysis.J Pharm Biomed Anal.2015 Mar 25;107:450-5. doi: 10.1016/j.jpba.2015.01.041. Epub 2015 Jan 25.
Chronic stress as well as major depressive disorders is associated with cortisol metabolism. Two enzymes modulate cortisol (F) and cortisone (E) interconversion: 11β-hydroxysteroid dehydrogenase type 1 and type 2 (11β-HSD1 and 11β-HSD2). Furthermore, F and E were inactivated by 5α and 5β reduct
PMID 25668797

Potential Corticoid Metabolites: Chemical Synthesis of 3- and 21-Monosulfates and Their Double-Conjugates of Tetrahydrocorticosteroids in the 5α- and 5β-Series

Okihara Rika,Mitamura Kuniko,Hasegawa Maki,Mori Megumi,Muto Akina,Kakiyama Genta,Ogawa Shoujiro,Iida Takashi,Shimada Miki,Mano Nariyasu,Ikegawa Shigeo
CHEMICAL & PHARMACEUTICAL BULLETIN 58(3), 344-353, 2010
… Here, we describe the chemical synthesis of the complete sets of 18 novel 3- and 21-monosulfates and their double-conjugated form of tetrahydrocortisol (THF), tetrahydro-11-deoxycortisol (THS), and tetrahydrocortisone (THE) in the 5α- and 5β-series. …
NAID 130000255911

Spironolactone Effective Hypertension in the Elderly Due to 11β-hydroxysteroid Dehydrogenase Type 2 (11β-HSD2) Impairment: Contributory Role of Determining Serum Cortisol/Cortisone Ratio as a Marker of 11β-HSD2 Activity

Inada Mitsuo,Iwasaki Keiko,Imai Chihiro,Hashimoto Satoshi
Internal Medicine 47(24), 2157-2164, 2008
… Significant elevations of urinary cortisol/cortisone ratios were observed, whereas urinary tetrahydrocortisol (THF)+allo-THF/tetrahydrocortisone (THE) ratios were not elevated significantly. …
NAID 130000079777