TETRAHYDROCORTISONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H32O5
Molecular Weight	364.4758
Optical Activity	UNSPECIFIED
Defined Stereocenters	8 / 8
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@]12CC(=O)[C@H]3[C@@H](CC[C@@H]4C[C@H](O)CC[C@]34C)[C@@H]1CC[C@]2(O)C(=O)CO

InChI

InChIKey=SYGWGHVTLUBCEM-ZIZPXRJBSA-N

InChI=1S/C21H32O5/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/h12-15,18,22-23,26H,3-11H2,1-2H3/t12-,13-,14+,15+,18-,19+,20+,21+/m1/s1

HIDE SMILES / InChI

Approval Year

PubMed

Title	Date	PubMed
The effect of high level tennis matches on urine steroid profiles in professional tennis players.	2010-12	21178940
Gas chromatography/mass spectrometry (GC/MS) remains a pre-eminent discovery tool in clinical steroid investigations even in the era of fast liquid chromatography tandem mass spectrometry (LC/MS/MS).	2010-08	20417277
Potential corticoid metabolites: chemical synthesis of 3- and 21-monosulfates and their double-conjugates of tetrahydrocorticosteroids in the 5alpha- and 5beta-series.	2010-03	20190439
Intense physical exercise increases systemic 11beta-hydroxysteroid dehydrogenase type 1 activity in healthy adult subjects.	2010-03	19902242
HPLC method for determination of fluorescence derivatives of cortisol, cortisone and their tetrahydro- and allo-tetrahydro-metabolites in biological fluids.	2010-02-01	20018571
11β-Hydroxysteroid dehydrogenase type-2 and type-1 (11β-HSD2 and 11β-HSD1) and 5β-reductase activities in the pathogenia of essential hypertension.	2010-02	19882252
Altered urinary profiles of endogenous steroids in postmenopausal women with adenocarcinoma endometrii.	2010-01	19670000
Steroid assays in paediatric endocrinology.	2010	21274330
Simultaneous determination of twelve tetrahydrocorticosteroid glucuronides in human urine by liquid chromatography/electrospray ionization-linear ion trap mass spectrometry.	2009-12-15	19874001
Determination of endocrine disrupting compounds using temperature-dependent inclusion chromatography: I. Optimization of separation protocol.	2009-10-30	19362314
Cortisol metabolic predictors of response to psychotherapy for symptoms of PTSD in survivors of the World Trade Center attacks on September 11, 2001.	2009-10	19411143
Heritable forms of hypertension.	2009-10	17647025
Application of hyphenated mass spectrometry techniques for the analysis of urinary free glucocorticoids.	2009-09	19681065
Urinary free cortisone, but not cortisol, is associated with urine volume in severe obesity.	2009-09	19541001
Effect of apolipoprotein a-I complex with tetrahydrocortisone on protein biosynthesis and glucose absorption by rat hepatocytes.	2009-08	20027330
Urinary steroid profile after the completion of concentric and concentric/eccentric trials with the same total workload.	2009-06	19886389
Recent advances in the assessment of the ratios of cortisol to cortisone and of some of their metabolites in urine by LC-MS-MS.	2009-04	19097044
Isotope ratio mass spectrometry analysis of the oxidation products of the main and minor metabolites of hydrocortisone and cortisone for antidoping controls.	2009-03	19056411
Diagnosis of diseases of steroid hormone production, metabolism and action.	2009	21274298
Cortisol metabolism in depressed patients and healthy controls.	2009	19713693
Daily urinary free cortisol and cortisone excretion is associated with urine volume in healthy children.	2008-12-22	18762206
Evaluation of urinary steroid profile in highly trained cyclists.	2008-12	18997659
Impaired glucose tolerance and insulin resistance are associated with increased adipose 11beta-hydroxysteroid dehydrogenase type 1 expression and elevated hepatic 5alpha-reductase activity.	2008-10	18633104
Simultaneous determination of tetrahydrocortisol, allotetrahydrocortisol and tetrahydrocortisone in human urine by liquid chromatography-electrospray ionization tandem mass spectrometry.	2008-08	18394666
Determination of urine steroid profile in untrained men to evaluate recovery after a strength training session.	2008-07	18545203
11beta-hydroxysteroid dehydrogenase 2 activity is elevated in severe obesity and negatively associated with insulin sensitivity.	2008-06	18421276
Development of a liquid chromatography-tandem mass spectrometry method for the determination of 23 endogenous steroids in small quantities of primate urine.	2008-02-01	18054529
Modulation of 11beta-hydroxysteroid dehydrogenase (11betaHSD) activity biomarkers and pharmacokinetics of PF-00915275, a selective 11betaHSD1 inhibitor.	2008-02	17986636
Simultaneous measurements of urinary free cortisol and cortisone for the assessment of functional glucocorticoid activity.	2007-10	17885143
Endogenous corticosteroid biosynthesis in subjects after bilateral adrenalectomy.	2007-05	17381495
Sex-specific difference in the interconversion of cortisol and cortisone in men and women.	2007-04	17426315
Inhibition of 11beta-hydroxysteroid dehydrogenase type 1 activity in vivo limits glucocorticoid exposure to human adipose tissue and decreases lipolysis.	2007-03	17200165
Variations in urine excretion of steroid hormones after an acute session and after a 4-week programme of strength training.	2007-01	17051372
[The urinary index of intracellular glucocorticoid reactivation--a novel marker of metabolic syndrome and type 2 diabetes].	2006-12-28	17458279
Apparent mineralocorticoid excess: report of six new cases and extensive personal experience.	2006-11	17035606
No effect of free fatty acids on adrenocorticotropin and cortisol secretion in healthy young men.	2006-08	16839836
Urinary cortisol and cortisol metabolite excretion in chronic fatigue syndrome.	2006-07-27	16868267
RP-HPLC method with fluorescence detection for determination of small quantities of triamcinolone in plasma in presence of endogenous steroids after derivatization with 9-anthroyl nitrile; pharmacokinetic studies.	2006-07-24	16551513
Pediatric renal allograft transplantation does not normalize the increased cortisol/cortisone ratios of chronic renal failure.	2006-04	16556718
Diurnal excretion of urinary cortisol, cortisone, and cortisol metabolites in chronic fatigue syndrome.	2006-02	16439267
Direct determination of the ratio of tetrahydrocortisol+allo-tetrahydrocortisol to tetrahydrocortisone in urine by LC-MS-MS.	2006-01-18	16310418
Comprehensive study of urinary cortisol metabolites in hyperthyroid and hypothyroid patients.	2006-01	16402926
Determination of free tetrahydrocortisol and tetrahydrocortisone ratio in urine by liquid chromatography-tandem mass spectrometry.	2006	16537248
11beta-Hydroxysteroid dehydrogenase type 2 activity is associated with left ventricular mass in essential hypertension.	2005-03	15618035
Comparison of the analysis of corticosteroids using different techniques.	2005-01	15700162
Activity of 11beta-hydroxysteroid dehydrogenase type 2 in normotensive blacks and whites.	2005	16108299
Urinary steroid excretion rates in acromegaly.	2005	15900108
Production rates of cortisol in obesity.	2004-09	15483206
Glucocorticoids contribute to the heritability of leptin in Scottish adult female twins.	2004-07	15212658
Endogenous urinary steroids in premenopausal women with uterine leiomyomas.	2004-01	14698830

Name

Type

Language

TETRAHYDROCORTISONE

Common Name

English

NSC-76984

Preferred Name

English

TETRAHYDROCORTISONE [MI]

Common Name

English

UROCORTISONE

Common Name

English

Classification Tree Code System Code

LOINC

82894-7