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
C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@]34C)[C@@H]1CC[C@H]2O
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
PubMed
| Title | Date | PubMed |
|---|---|---|
| Steroid profiles of professional soccer players: an international comparative study. | 2009-12 |
|
| Effects of recombinant human LH and hCG on serum and urine LH and androgens in men. | 2009-09 |
|
| Analysis of conjugated steroid androgens: deconjugation, derivatisation and associated issues. | 2009-07-12 |
|
| Quantification of testosterone and epitestosterone in biological samples by capillary electrophoresis with immunoaffinity extraction. | 2009-04-30 |
|
| First case of fatal pulmonary peliosis without any other organ involvement in a young testosterone abusing male. | 2009-04-15 |
|
| Determination of urinary androgen glucuronides by capillary electrophoresis with electrospray tandem mass spectrometry. | 2009-04 |
|
| Associations among hair loss, oral sulfur-containing gases, and gastrointestinal and metabolic linked diseases in Japanese elderly men: pilot study. | 2009-03-13 |
|
| Substantial advantage of a combined Bayesian and genotyping approach in testosterone doping tests. | 2009-03 |
|
| [Testosterone metabolism and doping test results]. | 2009-02-19 |
|
| UDP-glucuronosyltransferases (UGTs) 2B7 and UGT2B17 display converse specificity in testosterone and epitestosterone glucuronidation, whereas UGT2A1 conjugates both androgens similarly. | 2009-02 |
|
| Physiological concentrations of anabolic steroids in human hair. | 2009-01-30 |
|
| Sudden unexpected death in a female fitness athlete, with a possible connection to the use of anabolic androgenic steroids (AAS) and ephedrine. | 2009-01-30 |
|
| Evaluation of equine urine reactivity towards phase II metabolites of 17-hydroxy steroids by liquid chromatography/tandem mass spectrometry. | 2009-01 |
|
| Application of comprehensive two-dimensional gas chromatography to sterols analysis. | 2008-12-19 |
|
| Evaluation of urinary steroid profile in highly trained cyclists. | 2008-12 |
|
| Simultaneous measurement of boldenone (alpha and beta), ADD, testosterone, epitestosterone and AED in bovine faeces. | 2008-09 |
|
| 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. | 2008-08-15 |
|
| Isolation and quantification by high-performance liquid chromatography-ion-trap mass spectrometry of androgen sulfoconjugates in human urine. | 2008-07-04 |
|
| [Determination of endogenous anabolic steroids in hair using gas chromatography-tandem mass spectrometry]. | 2008-07 |
|
| Testosterone doping: dealing with genetic differences in metabolism and excretion. | 2008-07 |
|
| Factors influencing the steroid profile in doping control analysis. | 2008-07 |
|
| Quantitative confirmation of testosterone and epitestosterone in human urine by LC/Q-ToF mass spectrometry for doping control. | 2008-07 |
|
| Determination of urine steroid profile in untrained men to evaluate recovery after a strength training session. | 2008-07 |
|
| Determination of 13C/12C ratios of endogenous urinary steroids: method validation, reference population and application to doping control purposes. | 2008-07 |
|
| Ion trap MS/MS of intact testosterone and epitestosterone conjugates--adducts, fragile ions and the advantages of derivatisation. | 2008-07 |
|
| Doping test results dependent on genotype of uridine diphospho-glucuronosyl transferase 2B17, the major enzyme for testosterone glucuronidation. | 2008-07 |
|
| Genetic aspects of epitestosterone formation and androgen disposition: influence of polymorphisms in CYP17 and UGT2B enzymes. | 2008-06 |
|
| Multivariate optimization of a derivatisation procedure for the simultaneous determination of nine anabolic steroids by gas chromatography coupled with mass spectrometry. | 2008-05-09 |
|
| Evolution of pharmacologic specificity in the pregnane X receptor. | 2008-04-02 |
|
| Liquid chromatographic method development for anabolic androgenic steroids using a monolithic column Application to animal feed samples. | 2008-03-17 |
|
| Direct quantification of steroid glucuronides in human urine by liquid chromatography-electrospray tandem mass spectrometry. | 2008-03-07 |
|
| Comparison of partial filling MEKC analyses of steroids with use of ESI-MS and UV spectrophotometry. | 2008-03 |
|
| Androgen receptor transactivation assay using green fluorescent protein as a reporter. | 2008-02-15 |
|
| Urinary androgens and cortisol metabolites in field-sampled bonobos (Pan paniscus). | 2008-02-01 |
|
| From population- to subject-based limits of T/E ratio to detect testosterone abuse in elite sports. | 2008-01-30 |
|
| Evaluation of boldenone formation and related steroids transformations in veal faeces by liquid chromatography/tandem mass spectrometry. | 2008 |
|
| Determination of association constants between steroid compounds and albumins by partial-filling ACE. | 2007-10 |
|
| Tissue and serum levels of principal androgens in benign prostatic hyperplasia and prostate cancer. | 2007-04 |
|
| Bayesian detection of abnormal values in longitudinal biomarkers with an application to T/E ratio. | 2007-04 |
|
| 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. | 2007-02 |
|
| A diurnal variation in testicular hormone production is maintained following gonadotrophin suppression in normal men. | 2007-01 |
|
| Variations in urine excretion of steroid hormones after an acute session and after a 4-week programme of strength training. | 2007-01 |
|
| Sex, drugs and sports: prostaglandins, epitestosterone and sexual development. | 2007 |
|
| 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. | 2006-12-08 |
|
| Short-term stability of testosterone and epitestosterone conjugates in urine samples: quantification by liquid chromatography-linear ion trap mass spectrometry. | 2006-11-21 |
|
| Partial filling micellar electrokinetic chromatography analysis of androgens and testosterone derivatives using two sequential pseudostationary phases. | 2006-10-27 |
|
| Hormonal homeostasis in a group of 216 aging Czech males and correlation with responses to a questionnaire of the University of St Louis. | 2006-06 |
|
| Alternative methodology for the analysis of progesterone, testosterone, and epi-testosterone in bovine liver and veal muscle. | 2006-04-28 |
|
| [Determination of anabolic steroid hormones in animal muscle tissues by gas chromatography/mass spectrometry]. | 2006-01 |
|
| Rapid test by liquid chromatography/tandem mass spectrometry to evaluate equine urine reactivity towards 17beta-OH steroids. | 2006 |
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
| Substance Class |
Chemical
Created
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| Record UNII |
48L726977Z
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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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