TETRAHYDROCORTISOL

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H34O5
Molecular Weight	366.4917
Optical Activity	UNSPECIFIED
Defined Stereocenters	9 / 9
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@]12C[C@H](O)[C@H]3[C@@H](CC[C@@H]4C[C@H](O)CC[C@]34C)[C@@H]1CC[C@]2(O)C(=O)CO

InChI

InChIKey=AODPIQQILQLWGS-GXBDJPPSSA-N

InChI=1S/C21H34O5/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/h12-16,18,22-24,26H,3-11H2,1-2H3/t12-,13-,14+,15+,16+,18-,19+,20+,21+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C21H34O5
Molecular Weight	366.4917
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	9 / 9
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Apolipoprotein A-I 2 Target ID: P04639 Gene ID: 25081.0 Gene Symbol: Apoa1 Target Organism: Rattus norvegicus (Rat) Sources: https://www.ncbi.nlm.nih.gov/pubmed/18457017 \| https://www.ncbi.nlm.nih.gov/pubmed/14698212	Interacts 323

PubMed

Title	Date	PubMed
The effect of spironolactone upon corticosteroid hormone metabolism in patients with early stage chronic kidney disease.	2010-11	20550533
Bile acids modulate glucocorticoid metabolism and the hypothalamic-pituitary-adrenal axis in obstructive jaundice.	2010-05	20347173
Potential corticoid metabolites: chemical synthesis of 3- and 21-monosulfates and their double-conjugates of tetrahydrocorticosteroids in the 5alpha- and 5beta-series.	2010-03	20190439
Intense physical exercise increases systemic 11beta-hydroxysteroid dehydrogenase type 1 activity in healthy adult subjects.	2010-03	19902242
HPLC method for determination of fluorescence derivatives of cortisol, cortisone and their tetrahydro- and allo-tetrahydro-metabolites in biological fluids.	2010-02-01	20018571
11β-Hydroxysteroid dehydrogenase type-2 and type-1 (11β-HSD2 and 11β-HSD1) and 5β-reductase activities in the pathogenia of essential hypertension.	2010-02	19882252
Altered urinary profiles of endogenous steroids in postmenopausal women with adenocarcinoma endometrii.	2010-01	19670000
Tissue-specific increases in 11beta-hydroxysteroid dehydrogenase type 1 in normal weight postmenopausal women.	2009-12-29	20041117
Simultaneous determination of twelve tetrahydrocorticosteroid glucuronides in human urine by liquid chromatography/electrospray ionization-linear ion trap mass spectrometry.	2009-12-15	19874001
Determination of endocrine disrupting compounds using temperature-dependent inclusion chromatography: I. Optimization of separation protocol.	2009-10-30	19362314
Cortisol metabolic predictors of response to psychotherapy for symptoms of PTSD in survivors of the World Trade Center attacks on September 11, 2001.	2009-10	19411143
Heritable forms of hypertension.	2009-10	17647025
Application of hyphenated mass spectrometry techniques for the analysis of urinary free glucocorticoids.	2009-09	19681065
Urinary free cortisone, but not cortisol, is associated with urine volume in severe obesity.	2009-09	19541001
Role of DNA methylation in the tissue-specific expression of the CYP17A1 gene for steroidogenesis in rodents.	2009-07	19403566
Urinary steroid profile after the completion of concentric and concentric/eccentric trials with the same total workload.	2009-06	19886389
Enduring effects of severe developmental adversity, including nutritional deprivation, on cortisol metabolism in aging Holocaust survivors.	2009-06	19162277
The urinary steroid profile in patients diagnosed with adrenal incidentaloma.	2009-04	19297679
Recent advances in the assessment of the ratios of cortisol to cortisone and of some of their metabolites in urine by LC-MS-MS.	2009-04	19097044
Urine ratio of tetrahydrocortisol to tetrahydrodeoxycortisol to screen for the systemic administration of cortisone and hydrocortisone.	2009-03-10	19185436
Increased clearance of cortisol by 5beta-reductase in a subgroup of women with adrenal hyperandrogenism in polycystic ovary syndrome.	2009-03	19542736
Isotope ratio mass spectrometry analysis of the oxidation products of the main and minor metabolites of hydrocortisone and cortisone for antidoping controls.	2009-03	19056411
A randomized placebo-controlled study on the effects of pioglitazone on cortisol metabolism in polycystic ovary syndrome.	2009-03	18402944
Cortisol metabolism in depressed patients and healthy controls.	2009	19713693
Daily urinary free cortisol and cortisone excretion is associated with urine volume in healthy children.	2008-12-22	18762206
Evaluation of urinary steroid profile in highly trained cyclists.	2008-12	18997659
Impaired glucose tolerance and insulin resistance are associated with increased adipose 11beta-hydroxysteroid dehydrogenase type 1 expression and elevated hepatic 5alpha-reductase activity.	2008-10	18633104
Local and systemic glucocorticoid metabolism in inflammatory arthritis.	2008-09	18420938
Simultaneous determination of tetrahydrocortisol, allotetrahydrocortisol and tetrahydrocortisone in human urine by liquid chromatography-electrospray ionization tandem mass spectrometry.	2008-08	18394666
Epigenetic control of 11 beta-hydroxysteroid dehydrogenase 2 gene promoter is related to human hypertension.	2008-08	18178212
Determination of urine steroid profile in untrained men to evaluate recovery after a strength training session.	2008-07	18545203
11beta-hydroxysteroid dehydrogenase 2 activity is elevated in severe obesity and negatively associated with insulin sensitivity.	2008-06	18421276
[Mechanisms of interaction of tetrahydrocortisol and its complex with apolipoprotein A-I and DNA regulatory cis-elements of CC(GCC)5/GG(CGG)5 type].	2008-05-21	18488499
Urinary cortisol to cortisone metabolites ratio in prednisone-treated and spontaneously hypertensive patients.	2008-03	18300859
Development of a liquid chromatography-tandem mass spectrometry method for the determination of 23 endogenous steroids in small quantities of primate urine.	2008-02-01	18054529
Modulation of 11beta-hydroxysteroid dehydrogenase (11betaHSD) activity biomarkers and pharmacokinetics of PF-00915275, a selective 11betaHSD1 inhibitor.	2008-02	17986636
Interaction of apolipoproteins A-I and E in the regulation of DNA, RNA, and protein biosynthesis in cultured rat hepatocytes.	2007-12	18856200
[Structure of the interaction sites of eukaryotic DNA with steroid hormone-apolipoprotein A-I complexes].	2007-10-17	17936984
Simultaneous measurements of urinary free cortisol and cortisone for the assessment of functional glucocorticoid activity.	2007-10	17885143
Effect of complexes of apolipoprotein A-I with tetrahydrocortisol and pregnenolone on protein biosynthesis in rat hepatocytes culture.	2007-09	18457017
Reduced 11beta-hydroxysteroid dehydrogenase type 1 activity in obese boys.	2007-09	17766714
Endogenous corticosteroid biosynthesis in subjects after bilateral adrenalectomy.	2007-05	17381495
Sex-specific difference in the interconversion of cortisol and cortisone in men and women.	2007-04	17426315
MR imaging of therapy-induced changes of bone marrow.	2007-03	17021706
Variations in urine excretion of steroid hormones after an acute session and after a 4-week programme of strength training.	2007-01	17051372
[Effect of apolipoprotein A-1 containing steroid hormones on DNA and protein biosynthesis in cells of ascitic hepatoma HA-1].	2007	18154121
[The urinary index of intracellular glucocorticoid reactivation--a novel marker of metabolic syndrome and type 2 diabetes].	2006-12-28	17458279
Apparent mineralocorticoid excess: report of six new cases and extensive personal experience.	2006-11	17035606
No effect of free fatty acids on adrenocorticotropin and cortisol secretion in healthy young men.	2006-08	16839836
Urinary cortisol and cortisol metabolite excretion in chronic fatigue syndrome.	2006-07-27	16868267

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:54:01 GMT 2025` Edited by `admin` on `Mon Mar 31 17:54:01 GMT 2025`
Record UNII	7P2O6MFN8O
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BA-2682

Preferred Name

English

TETRAHYDROCORTISOL

Common Name

English

TETRAHYDROHYDROCORTISONE

Common Name

English

3.ALPHA.,11.BETA.,17,21-TETROL-5.BETA.-PREGNAN-20-ONE

Common Name

English

5.BETA.-PREGNAN-20-ONE, 3.ALPHA.,11.BETA.,17,21-TETRAHYDROXY-

Systematic Name

English

3.ALPHA.,11.BETA.,17.ALPHA.,21-TETRAHYDROXY-5.BETA.-PREGNAN-20-ONE

Common Name

English

5.BETA.-PREGNANE-3.ALPHA.,11.BETA.,17.ALPHA.,21-TETROL-20-ONE

Common Name

English

3,11,17,21-TETRAHYDROXYPREGNAN-20-ONE, (3.ALPHA.,5.BETA.,11.BETA.)-

Systematic Name

English

UROCORTISOL

Common Name

English

CORTISOL, TETRAHYDRO-

Common Name

English

NSC-57431

Code

English

3.ALPHA.,11.BETA.,17,21-TETRAHYDROXY-5.BETA.-PREGNAN-20-ONE

Systematic Name

English

5.BETA.-TETRAHYDROCORTISOL

Common Name

English

PREGNAN-20-ONE, 3,11,17,21-TETRAHYDROXY-, (3.ALPHA.,5.BETA.,11.BETA.)-

Systematic Name

English

TETRAHYDROCOMPOUND F

Common Name

English

TETRAHYDRO F

Common Name

English

Classification Tree Code System Code

LOINC

82895-4