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
Synthesis of deuterium-labeled tetrahydrocortisol and tetrahydrocortisone for study of cortisol metabolism in humans.	1999 Dec	10576214
In vivo 11beta-HSD-2 activity: variability, salt-sensitivity, and effect of licorice.	2001 Dec 1	11751713
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	11167935
Modulation of cortisol metabolism by the growth hormone receptor antagonist pegvisomant in patients with acromegaly.	2001 Jul	11443156
Interference by danazol with the Porter-Silber method for determination of urinary 17-hydroxycorticosteroids.	2001 May	11392505
Steroid hormone metabolism in women with pelvic organ prolapse.	2002 Apr	12012882
Role of ketoconazole treatment in urinary-free cortisol-to-cortisone and tetrahydrocortisol-to-tetrahydrocortisone ratios in nonectopic Cushing's syndrome.	2002 Aug	12450320
11beta-hydroxysteroid dehydrogenase activity in proteinuric patients and the effect of angiotensin-II receptor blockade.	2002 Jul	12153552
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	12071853
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
Glucocorticoids contribute to the heritability of leptin in Scottish adult female twins.	2004 Jul	15212658
Production rates of cortisol in obesity.	2004 Sep	15483206
Urinary steroid excretion rates in acromegaly.	2005	15900108
11beta-Hydroxysteroid dehydrogenase type 2 activity is associated with left ventricular mass in essential hypertension.	2005 Mar	15618035
Determination of free tetrahydrocortisol and tetrahydrocortisone ratio in urine by liquid chromatography-tandem mass spectrometry.	2006	16537248
[The urinary index of intracellular glucocorticoid reactivation--a novel marker of metabolic syndrome and type 2 diabetes].	2006 Dec 28	17458279
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
Apparent mineralocorticoid excess: report of six new cases and extensive personal experience.	2006 Nov	17035606
Variations in urine excretion of steroid hormones after an acute session and after a 4-week programme of strength training.	2007 Jan	17051372
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
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
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
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
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
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
Application of hyphenated mass spectrometry techniques for the analysis of urinary free glucocorticoids.	2009 Sep	19681065
Urinary free cortisone, but not cortisol, is associated with urine volume in severe obesity.	2009 Sep	19541001
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

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

Common Name

English

TETRAHYDROCORTISONE [MI]

Common Name

English

UROCORTISONE

Common Name

English

NSC-76984

Code

English

Classification Tree Code System Code

LOINC

82894-7