U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of TETRAHYDROCORTISONE

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

PubMed

TitleDatePubMed
Synthesis of deuterium-labeled tetrahydrocortisol and tetrahydrocortisone for study of cortisol metabolism in humans.
1999 Dec
In vivo 11beta-HSD-2 activity: variability, salt-sensitivity, and effect of licorice.
2001 Dec 1
Toxic multinodular goitre in a patient with generalized resistance to thyroid hormone who harbours the R429Q mutation in the thyroid hormone receptor beta gene.
2001 Jan
Modulation of cortisol metabolism by the growth hormone receptor antagonist pegvisomant in patients with acromegaly.
2001 Jul
Interference by danazol with the Porter-Silber method for determination of urinary 17-hydroxycorticosteroids.
2001 May
Steroid hormone metabolism in women with pelvic organ prolapse.
2002 Apr
Role of ketoconazole treatment in urinary-free cortisol-to-cortisone and tetrahydrocortisol-to-tetrahydrocortisone ratios in nonectopic Cushing's syndrome.
2002 Aug
11beta-hydroxysteroid dehydrogenase activity in proteinuric patients and the effect of angiotensin-II receptor blockade.
2002 Jul
Isolation and characterization of the monkey UGT2B30 gene that encodes a uridine diphosphate-glucuronosyltransferase enzyme active on mineralocorticoid, glucocorticoid, androgen and oestrogen hormones.
2002 Jul 1
Increased cortisol metabolites and reduced activity of 11beta-hydroxysteroid dehydrogenase in patients on hemodialysis.
2002 May
Modulation of renal calcium handling by 11 beta-hydroxysteroid dehydrogenase type 2.
2002 Oct
11beta-hydroxysteroid dehydrogenase type 1 deficiency ('apparent cortisone reductase deficiency') in a 6-year-old boy.
2003
Altered cortisol metabolism in polycystic ovary syndrome: insulin enhances 5alpha-reduction but not the elevated adrenal steroid production rates.
2003 Dec
Endogenous urinary steroids in premenopausal women with uterine leiomyomas.
2004 Jan
Glucocorticoids contribute to the heritability of leptin in Scottish adult female twins.
2004 Jul
Production rates of cortisol in obesity.
2004 Sep
Urinary steroid excretion rates in acromegaly.
2005
11beta-Hydroxysteroid dehydrogenase type 2 activity is associated with left ventricular mass in essential hypertension.
2005 Mar
Determination of free tetrahydrocortisol and tetrahydrocortisone ratio in urine by liquid chromatography-tandem mass spectrometry.
2006
[The urinary index of intracellular glucocorticoid reactivation--a novel marker of metabolic syndrome and type 2 diabetes].
2006 Dec 28
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
Urinary cortisol and cortisol metabolite excretion in chronic fatigue syndrome.
2006 Jul-Aug
Apparent mineralocorticoid excess: report of six new cases and extensive personal experience.
2006 Nov
Variations in urine excretion of steroid hormones after an acute session and after a 4-week programme of strength training.
2007 Jan
Simultaneous measurements of urinary free cortisol and cortisone for the assessment of functional glucocorticoid activity.
2007 Oct
Simultaneous determination of tetrahydrocortisol, allotetrahydrocortisol and tetrahydrocortisone in human urine by liquid chromatography-electrospray ionization tandem mass spectrometry.
2008 Aug
Evaluation of urinary steroid profile in highly trained cyclists.
2008 Dec
Daily urinary free cortisol and cortisone excretion is associated with urine volume in healthy children.
2008 Dec 22
Modulation of 11beta-hydroxysteroid dehydrogenase (11betaHSD) activity biomarkers and pharmacokinetics of PF-00915275, a selective 11betaHSD1 inhibitor.
2008 Feb
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
Determination of urine steroid profile in untrained men to evaluate recovery after a strength training session.
2008 Jul
11beta-hydroxysteroid dehydrogenase 2 activity is elevated in severe obesity and negatively associated with insulin sensitivity.
2008 Jun
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
Diagnosis of diseases of steroid hormone production, metabolism and action.
2009
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
Effect of apolipoprotein a-I complex with tetrahydrocortisone on protein biosynthesis and glucose absorption by rat hepatocytes.
2009 Aug
Simultaneous determination of twelve tetrahydrocorticosteroid glucuronides in human urine by liquid chromatography/electrospray ionization-linear ion trap mass spectrometry.
2009 Dec 15
Isotope ratio mass spectrometry analysis of the oxidation products of the main and minor metabolites of hydrocortisone and cortisone for antidoping controls.
2009 Mar
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
Heritable forms of hypertension.
2009 Oct
Determination of endocrine disrupting compounds using temperature-dependent inclusion chromatography: I. Optimization of separation protocol.
2009 Oct 30
Application of hyphenated mass spectrometry techniques for the analysis of urinary free glucocorticoids.
2009 Sep
Urinary free cortisone, but not cortisol, is associated with urine volume in severe obesity.
2009 Sep
Steroid assays in paediatric endocrinology.
2010
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
The effect of high level tennis matches on urine steroid profiles in professional tennis players.
2010 Dec
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
HPLC method for determination of fluorescence derivatives of cortisol, cortisone and their tetrahydro- and allo-tetrahydro-metabolites in biological fluids.
2010 Feb 1
Altered urinary profiles of endogenous steroids in postmenopausal women with adenocarcinoma endometrii.
2010 Jan
Potential corticoid metabolites: chemical synthesis of 3- and 21-monosulfates and their double-conjugates of tetrahydrocorticosteroids in the 5alpha- and 5beta-series.
2010 Mar
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
  • Download
Name Type Language
TETRAHYDROCORTISONE
MI  
Common Name English
TETRAHYDROCORTISONE [MI]
Common Name English
UROCORTISONE
Common Name English
NSC-76984
Code English
Classification Tree Code System Code
LOINC 82894-7
Created by admin on Sat Jun 26 02:56:11 UTC 2021 , Edited by admin on Sat Jun 26 02:56:11 UTC 2021
LOINC 82895-4
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LOINC 82851-7
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LOINC 73894-8
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LOINC 82896-2
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LOINC 82878-0
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LOINC 82901-0
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LOINC 82879-8
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LOINC 82849-1
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LOINC 82848-3
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LOINC 82857-4
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LOINC 82862-4
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LOINC 82855-8
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LOINC 82900-2
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LOINC 82899-6
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LOINC 82854-1
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LOINC 81795-7
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LOINC 82856-6
Created by admin on Sat Jun 26 02:56:11 UTC 2021 , Edited by admin on Sat Jun 26 02:56:11 UTC 2021
LOINC 82861-6
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LOINC 82898-8
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LOINC 73893-0
Created by admin on Sat Jun 26 02:56:11 UTC 2021 , Edited by admin on Sat Jun 26 02:56:11 UTC 2021
LOINC 82850-9
Created by admin on Sat Jun 26 02:56:11 UTC 2021 , Edited by admin on Sat Jun 26 02:56:11 UTC 2021
LOINC 82897-0
Created by admin on Sat Jun 26 02:56:11 UTC 2021 , Edited by admin on Sat Jun 26 02:56:11 UTC 2021
Code System Code Type Description
WIKIPEDIA
TETRAHYDROCORTISONE
Created by admin on Sat Jun 26 02:56:11 UTC 2021 , Edited by admin on Sat Jun 26 02:56:11 UTC 2021
PRIMARY
MERCK INDEX
M10625
Created by admin on Sat Jun 26 02:56:11 UTC 2021 , Edited by admin on Sat Jun 26 02:56:11 UTC 2021
PRIMARY Merck Index
PUBCHEM
5866
Created by admin on Sat Jun 26 02:56:11 UTC 2021 , Edited by admin on Sat Jun 26 02:56:11 UTC 2021
PRIMARY
FDA UNII
5HF9TM2D15
Created by admin on Sat Jun 26 02:56:11 UTC 2021 , Edited by admin on Sat Jun 26 02:56:11 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-161-9
Created by admin on Sat Jun 26 02:56:11 UTC 2021 , Edited by admin on Sat Jun 26 02:56:11 UTC 2021
PRIMARY
CAS
53-05-4
Created by admin on Sat Jun 26 02:56:11 UTC 2021 , Edited by admin on Sat Jun 26 02:56:11 UTC 2021
PRIMARY
Related Record Type Details
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