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

Molecular Formula	C21H32O5
Molecular Weight	364.4758
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
In vivo 11beta-HSD-2 activity: variability, salt-sensitivity, and effect of licorice.	2001 Dec 1	11751713
Role of ketoconazole treatment in urinary-free cortisol-to-cortisone and tetrahydrocortisol-to-tetrahydrocortisone ratios in nonectopic Cushing's syndrome.	2002 Aug	12450320
Modulation of renal calcium handling by 11 beta-hydroxysteroid dehydrogenase type 2.	2002 Oct	12239243
Production rates of cortisol in obesity.	2004 Sep	15483206
Urinary steroid excretion rates in acromegaly.	2005	15900108
Comparison of the analysis of corticosteroids using different techniques.	2005 Jan	15700162
Activity of 11beta-hydroxysteroid dehydrogenase type 2 in normotensive blacks and whites.	2005 Summer	16108299
[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
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
Simultaneous measurements of urinary free cortisol and cortisone for the assessment of functional glucocorticoid activity.	2007 Oct	17885143
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
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
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
Cortisol metabolic predictors of response to psychotherapy for symptoms of PTSD in survivors of the World Trade Center attacks on September 11, 2001.	2009 Oct	19411143
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
Urinary free cortisone, but not cortisol, is associated with urine volume in severe obesity.	2009 Sep	19541001
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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 14:57:36 UTC 2023` Edited by `admin` on `Fri Dec 15 14:57:36 UTC 2023`
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