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

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

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
Synthesis of deuterium-labeled tetrahydrocortisol and tetrahydrocortisone for study of cortisol metabolism in humans.	1999 Dec	10576214
Modulation of cortisol metabolism by the growth hormone receptor antagonist pegvisomant in patients with acromegaly.	2001 Jul	11443156
11beta-hydroxysteroid dehydrogenase activity in proteinuric patients and the effect of angiotensin-II receptor blockade.	2002 Jul	12153552
Increased cortisol metabolites and reduced activity of 11beta-hydroxysteroid dehydrogenase in patients on hemodialysis.	2002 May	11967038
Modulation of renal calcium handling by 11 beta-hydroxysteroid dehydrogenase type 2.	2002 Oct	12239243
11beta-hydroxysteroid dehydrogenase type 1 deficiency ('apparent cortisone reductase deficiency') in a 6-year-old boy.	2003	12649576
Altered cortisol metabolism in polycystic ovary syndrome: insulin enhances 5alpha-reduction but not the elevated adrenal steroid production rates.	2003 Dec	14671189
Endogenous urinary steroids in premenopausal women with uterine leiomyomas.	2004 Jan	14698830
Production rates of cortisol in obesity.	2004 Sep	15483206
Activity of 11beta-hydroxysteroid dehydrogenase type 2 in normotensive blacks and whites.	2005 Summer	16108299
Determination of free tetrahydrocortisol and tetrahydrocortisone ratio in urine by liquid chromatography-tandem mass spectrometry.	2006	16537248
No effect of free fatty acids on adrenocorticotropin and cortisol secretion in healthy young men.	2006 Aug	16839836
Diurnal excretion of urinary cortisol, cortisone, and cortisol metabolites in chronic fatigue syndrome.	2006 Feb	16439267
Direct determination of the ratio of tetrahydrocortisol+allo-tetrahydrocortisol to tetrahydrocortisone in urine by LC-MS-MS.	2006 Jan 18	16310418
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 Jul 24	16551513
Urinary cortisol and cortisol metabolite excretion in chronic fatigue syndrome.	2006 Jul-Aug	16868267
Variations in urine excretion of steroid hormones after an acute session and after a 4-week programme of strength training.	2007 Jan	17051372
Simultaneous determination of tetrahydrocortisol, allotetrahydrocortisol and tetrahydrocortisone in human urine by liquid chromatography-electrospray ionization tandem mass spectrometry.	2008 Aug	18394666
Evaluation of urinary steroid profile in highly trained cyclists.	2008 Dec	18997659
Daily urinary free cortisol and cortisone excretion is associated with urine volume in healthy children.	2008 Dec 22	18762206
Modulation of 11beta-hydroxysteroid dehydrogenase (11betaHSD) activity biomarkers and pharmacokinetics of PF-00915275, a selective 11betaHSD1 inhibitor.	2008 Feb	17986636
Development of a liquid chromatography-tandem mass spectrometry method for the determination of 23 endogenous steroids in small quantities of primate urine.	2008 Feb 1	18054529
Determination of urine steroid profile in untrained men to evaluate recovery after a strength training session.	2008 Jul	18545203
11beta-hydroxysteroid dehydrogenase 2 activity is elevated in severe obesity and negatively associated with insulin sensitivity.	2008 Jun	18421276
Impaired glucose tolerance and insulin resistance are associated with increased adipose 11beta-hydroxysteroid dehydrogenase type 1 expression and elevated hepatic 5alpha-reductase activity.	2008 Oct	18633104
Diagnosis of diseases of steroid hormone production, metabolism and action.	2009	21274298
Cortisol metabolism in depressed patients and healthy controls.	2009	19713693
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 Apr	19097044
Simultaneous determination of twelve tetrahydrocorticosteroid glucuronides in human urine by liquid chromatography/electrospray ionization-linear ion trap mass spectrometry.	2009 Dec 15	19874001
Urinary steroid profile after the completion of concentric and concentric/eccentric trials with the same total workload.	2009 Jun	19886389
Isotope ratio mass spectrometry analysis of the oxidation products of the main and minor metabolites of hydrocortisone and cortisone for antidoping controls.	2009 Mar	19056411
Application of hyphenated mass spectrometry techniques for the analysis of urinary free glucocorticoids.	2009 Sep	19681065
Steroid assays in paediatric endocrinology.	2010	21274330
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 Aug	20417277
The effect of high level tennis matches on urine steroid profiles in professional tennis players.	2010 Dec	21178940
11β-Hydroxysteroid dehydrogenase type-2 and type-1 (11β-HSD2 and 11β-HSD1) and 5β-reductase activities in the pathogenia of essential hypertension.	2010 Feb	19882252
Potential corticoid metabolites: chemical synthesis of 3- and 21-monosulfates and their double-conjugates of tetrahydrocorticosteroids in the 5alpha- and 5beta-series.	2010 Mar	20190439
Intense physical exercise increases systemic 11beta-hydroxysteroid dehydrogenase type 1 activity in healthy adult subjects.	2010 Mar	19902242

Name

Type

Language

TETRAHYDROCORTISONE

Common Name

English

TETRAHYDROCORTISONE [MI]

Common Name

English

UROCORTISONE

Common Name

English

NSC-76984

Code

English

Classification Tree Code System Code

LOINC

82894-7