TETRAHYDROCORTISONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H32O5
Molecular Weight	364.4766
Optical Activity	UNSPECIFIED
Defined Stereocenters	8 / 8
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@@]12CC[C@]([H])(C[C@@]2([H])CC[C@@]3([H])[C@]4([H])CC[C@](C(=O)CO)([C@@]4(C)CC(=O)[C@@]31[H])O)O

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

Molecular Formula	C21H32O5
Molecular Weight	364.4766
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	8 / 8
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

PubMed

Title	Date	PubMed
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 2 activity is associated with left ventricular mass in essential hypertension.	2005 Mar	15618035
[The urinary index of intracellular glucocorticoid reactivation--a novel marker of metabolic syndrome and type 2 diabetes].	2006 Dec 28	17458279
Comprehensive study of urinary cortisol metabolites in hyperthyroid and hypothyroid patients.	2006 Jan	16402926
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
Sex-specific difference in the interconversion of cortisol and cortisone in men and women.	2007 Apr	17426315
Inhibition of 11beta-hydroxysteroid dehydrogenase type 1 activity in vivo limits glucocorticoid exposure to human adipose tissue and decreases lipolysis.	2007 Mar	17200165
Simultaneous measurements of urinary free cortisol and cortisone for the assessment of functional glucocorticoid activity.	2007 Oct	17885143
Simultaneous determination of tetrahydrocortisol, allotetrahydrocortisol and tetrahydrocortisone in human urine by liquid chromatography-electrospray ionization tandem mass spectrometry.	2008 Aug	18394666
Daily urinary free cortisol and cortisone excretion is associated with urine volume in healthy children.	2008 Dec 22	18762206
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
Diagnosis of diseases of steroid hormone production, metabolism and action.	2009	21274298
Cortisol metabolism in depressed patients and healthy controls.	2009	19713693
Effect of apolipoprotein a-I complex with tetrahydrocortisone on protein biosynthesis and glucose absorption by rat hepatocytes.	2009 Aug	20027330
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
Heritable forms of hypertension.	2009 Oct	17647025
Determination of endocrine disrupting compounds using temperature-dependent inclusion chromatography: I. Optimization of separation protocol.	2009 Oct 30	19362314
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
HPLC method for determination of fluorescence derivatives of cortisol, cortisone and their tetrahydro- and allo-tetrahydro-metabolites in biological fluids.	2010 Feb 1	20018571
Altered urinary profiles of endogenous steroids in postmenopausal women with adenocarcinoma endometrii.	2010 Jan	19670000
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

Substance Class	Chemical Created by `admin` on `Sat Jun 26 02:56:11 UTC 2021` Edited by `admin` on `Sat Jun 26 02:56:11 UTC 2021`
Record UNII	5HF9TM2D15
Record Status	`Validated (UNII)`
Record Version

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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