Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C19H28O2 |
Molecular Weight | 288.4244 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CC[C@@H](O)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CCC4=CC(=O)CC[C@]34C
InChI
InChIKey=MUMGGOZAMZWBJJ-KZYORJDKSA-N
InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-17,21H,3-10H2,1-2H3/t14-,15-,16-,17+,18-,19-/m0/s1
Molecular Formula | C19H28O2 |
Molecular Weight | 288.4244 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Epitestosterone (17alpha-hydroxy-4-androsten-3-one) is a naturally occurring epimer of testosterone. It apparently parallels the formation of testosterone, but on the other hand its concentration is not influenced by exogenous administration of testosterone. This fact creates the basis of the present doping control of testosterone abuse. Epitestosterone can be considered as a weak antiandrogen in the term of displacement of androgen from receptor binding and as an efficient inhibitor of 5 alpha-reductase. Epitestosterone exerts androgen receptor-independent neuroprotective activity in vitro.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6208540 |
860.0 nM [Ki] | ||
Target ID: CHEMBL3072 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2532272 |
29.8 nM [Ki] | ||
Target ID: CHEMBL2363075 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2532272 |
1.2 µM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Diagnostic | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
[Effect of chorionic gonadotropin on the urinary excretion of testosterone and other androgens in healthy men and those with coronary arteriosclerosis]. | 1979 Jun |
|
The in vitro enzymic labilities of chemically distinct phosphomonoester prodrugs. | 1992 Apr |
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Antiandrogenic activity of epitestosterone in male mice in vivo. | 2001 |
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Gas chromatography/combustion/isotope ratio mass spectrometry to control the misuse of androgens in breeding animals: new derivatisation method applied to testosterone metabolites and precursors in urine samples. | 2001 |
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Hair analysis of seven bodybuilders for anabolic steroids, ephedrine, and clenbuterol. | 2002 Jan |
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Effects of androstenedione administration on epitestosterone metabolism in men. | 2002 Jun |
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Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor. | 2003 Oct |
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Hormonal profile of men with premature balding. | 2004 Jan |
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Delayed effects of short-term transdermal application of 7-oxo-dehydroepiandrosterone on its metabolites, some hormonal steroids and relevant proteohormones in healthy male volunteers. | 2005 |
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Extraction of testosterone and epitestosterone in human urine using aqueous two-phase systems of ionic liquid and salt. | 2005 Aug 5 |
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Evidence that 17alpha-estradiol is biologically active in the uterine tissue: antiuterotonic and antiuterotrophic action. | 2005 Jul 21 |
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Urinary marker of oral pregnenolone administration. | 2005 Mar |
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Stability studies of testosterone and epitestosterone glucuronides in urine. | 2006 |
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Application of stable carbon isotope analysis to the detection of testosterone administration to cattle. | 2006 Apr 19 |
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Crystal structures of mouse 17alpha-hydroxysteroid dehydrogenase (apoenzyme and enzyme-NADP(H) binary complex): identification of molecular determinants responsible for the unique 17alpha-reductive activity of this enzyme. | 2006 Dec 8 |
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Neoformation of boldenone and related steroids in faeces of veal calves. | 2006 Feb |
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[Determination of anabolic steroid hormones in animal muscle tissues by gas chromatography/mass spectrometry]. | 2006 Jan |
|
Alternative methodology for the analysis of progesterone, testosterone, and epi-testosterone in bovine liver and veal muscle. | 2006 Mar-Apr |
|
Development of a faster determination of 10 anabolic steroids residues in animal muscle tissues by liquid chromatography tandem mass spectrometry. | 2006 May 3 |
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Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006 Nov |
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Short-term stability of testosterone and epitestosterone conjugates in urine samples: quantification by liquid chromatography-linear ion trap mass spectrometry. | 2006 Nov 21 |
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Partial filling micellar electrokinetic chromatography analysis of androgens and testosterone derivatives using two sequential pseudostationary phases. | 2006 Oct 27 |
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Tissue and serum levels of principal androgens in benign prostatic hyperplasia and prostate cancer. | 2007 Apr |
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Bayesian detection of abnormal values in longitudinal biomarkers with an application to T/E ratio. | 2007 Apr |
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Quantification of testosterone and epitestosterone in human urine samples by stir bar sorptive extraction--thermal desorption--gas chromatography/mass spectrometry: application to HIV-positive urine samples. | 2007 Feb |
|
A diurnal variation in testicular hormone production is maintained following gonadotrophin suppression in normal men. | 2007 Jan |
|
Variations in urine excretion of steroid hormones after an acute session and after a 4-week programme of strength training. | 2007 Jan |
|
Determination of association constants between steroid compounds and albumins by partial-filling ACE. | 2007 Oct |
|
Evolution of pharmacologic specificity in the pregnane X receptor. | 2008 Apr 2 |
|
Analysis of steroids in yeast-mediated cell culture by on-line solid-phase extraction coupled high-performance liquid chromatography electrospray-ionization/mass spectrometry and novel continuous postcolumn infusion of internal standard technique. | 2008 Aug 15 |
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Evaluation of urinary steroid profile in highly trained cyclists. | 2008 Dec |
|
Application of comprehensive two-dimensional gas chromatography to sterols analysis. | 2008 Dec 19 |
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Urinary androgens and cortisol metabolites in field-sampled bonobos (Pan paniscus). | 2008 Feb 1 |
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Androgen receptor transactivation assay using green fluorescent protein as a reporter. | 2008 Feb 15 |
|
From population- to subject-based limits of T/E ratio to detect testosterone abuse in elite sports. | 2008 Jan 30 |
|
[Determination of endogenous anabolic steroids in hair using gas chromatography-tandem mass spectrometry]. | 2008 Jul |
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Testosterone doping: dealing with genetic differences in metabolism and excretion. | 2008 Jul |
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Quantitative confirmation of testosterone and epitestosterone in human urine by LC/Q-ToF mass spectrometry for doping control. | 2008 Jul |
|
Determination of urine steroid profile in untrained men to evaluate recovery after a strength training session. | 2008 Jul |
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Determination of 13C/12C ratios of endogenous urinary steroids: method validation, reference population and application to doping control purposes. | 2008 Jul |
|
Ion trap MS/MS of intact testosterone and epitestosterone conjugates--adducts, fragile ions and the advantages of derivatisation. | 2008 Jul |
|
Isolation and quantification by high-performance liquid chromatography-ion-trap mass spectrometry of androgen sulfoconjugates in human urine. | 2008 Jul 4 |
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Genetic aspects of epitestosterone formation and androgen disposition: influence of polymorphisms in CYP17 and UGT2B enzymes. | 2008 Jun |
|
Simultaneous measurement of boldenone (alpha and beta), ADD, testosterone, epitestosterone and AED in bovine faeces. | 2008 Sep |
|
First case of fatal pulmonary peliosis without any other organ involvement in a young testosterone abusing male. | 2009 Apr 15 |
|
Quantification of testosterone and epitestosterone in biological samples by capillary electrophoresis with immunoaffinity extraction. | 2009 Apr 30 |
|
Steroid profiles of professional soccer players: an international comparative study. | 2009 Dec |
|
[Testosterone metabolism and doping test results]. | 2009 Jan-Feb |
|
Analysis of conjugated steroid androgens: deconjugation, derivatisation and associated issues. | 2009 Jul 12 |
|
Associations among hair loss, oral sulfur-containing gases, and gastrointestinal and metabolic linked diseases in Japanese elderly men: pilot study. | 2009 Mar 13 |
Patents
Sample Use Guides
In animal studies, epitestosterone was injected or delivered by means of silastic capsules of different lengths. Dosage is not specified.
Route of Administration:
Parenteral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11389183
The anti-androgen, 4 nM epitestosterone (the concentration represents peak physiological levels in reproductive age women and men) reduced apoptosis in primary cultures of human neurons induced to undergo apoptosis by serum deprivation.
Substance Class |
Chemical
Created
by
admin
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Edited
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Record UNII |
48L726977Z
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Record Status |
Validated (UNII)
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Record Version |
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Related Record | Type | Details | ||
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PARENT -> METABOLITE |
URINE
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Related Record | Type | Details | ||
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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