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
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
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 |
---|---|---|
Synthesis of deuterium-labeled tetrahydrocortisol and tetrahydrocortisone for study of cortisol metabolism in humans. | 1999 Dec |
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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 |
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Modulation of cortisol metabolism by the growth hormone receptor antagonist pegvisomant in patients with acromegaly. | 2001 Jul |
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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 |
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Role of ketoconazole treatment in urinary-free cortisol-to-cortisone and tetrahydrocortisol-to-tetrahydrocortisone ratios in nonectopic Cushing's syndrome. | 2002 Aug |
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11beta-hydroxysteroid dehydrogenase activity in proteinuric patients and the effect of angiotensin-II receptor blockade. | 2002 Jul |
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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 |
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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
Edited
Sat Jun 26 02:56:11 UTC 2021
by
admin
on
Sat Jun 26 02:56:11 UTC 2021
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Record UNII |
5HF9TM2D15
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Record Status |
Validated (UNII)
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Record Version |
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Code System | Code | Type | Description | ||
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TETRAHYDROCORTISONE
Created by
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M10625
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PRIMARY | Merck Index | ||
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5866
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5HF9TM2D15
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200-161-9
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53-05-4
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