Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C19H28O2 |
| Molecular Weight | 288.4251 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 6 / 6 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@@]12CCC(=O)C=C2CC[C@@]3([H])[C@]4([H])CC[C@]([H])([C@@]4(C)CC[C@@]31[H])O
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 | 288.4251 |
| 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 |
|---|---|---|
| [Effect of chorionic gonadotropin on the urinary excretion of testosterone and other androgens in healthy men and those with coronary arteriosclerosis]. | 1979 Jun |
|
| Urinary excretion of steroid metabolites after chronic androstenedione ingestion. | 2004 Dec |
|
| Urinary analysis of four testosterone metabolites and pregnanediol by gas chromatography-combustion-isotope ratio mass spectrometry after oral administrations of testosterone. | 2004 Sep |
|
| ADD, AED, alpha-boldenone and epitestosterone neo formation in calf faeces: preliminary results. | 2005 Aug |
|
| Extraction of testosterone and epitestosterone in human urine using aqueous two-phase systems of ionic liquid and salt. | 2005 Aug 5 |
|
| Evidence that 17alpha-estradiol is biologically active in the uterine tissue: antiuterotonic and antiuterotrophic action. | 2005 Jul 21 |
|
| Urine steroid profile of judo competitors affected by acute physical exercises. | 2005 Sep |
|
| Rapid test by liquid chromatography/tandem mass spectrometry to evaluate equine urine reactivity towards 17beta-OH steroids. | 2006 |
|
| 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 |
|
| [Determination of anabolic steroid hormones in animal muscle tissues by gas chromatography/mass spectrometry]. | 2006 Jan |
|
| Hormonal homeostasis in a group of 216 aging Czech males and correlation with responses to a questionnaire of the University of St Louis. | 2006 Jun |
|
| Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006 Nov |
|
| Elevated and similar urinary testosterone/epitestosterone ratio in all samples of a competition testing: suspicion of a manipulation. | 2006 Nov 10 |
|
| Short-term stability of testosterone and epitestosterone conjugates in urine samples: quantification by liquid chromatography-linear ion trap mass spectrometry. | 2006 Nov 21 |
|
| Partial filling micellar electrokinetic chromatography analysis of androgens and testosterone derivatives using two sequential pseudostationary phases. | 2006 Oct 27 |
|
| Sex, drugs and sports: prostaglandins, epitestosterone and sexual development. | 2007 |
|
| Tissue and serum levels of principal androgens in benign prostatic hyperplasia and prostate cancer. | 2007 Apr |
|
| 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 |
|
| Evaluation of urinary steroid profile in highly trained cyclists. | 2008 Dec |
|
| Application of comprehensive two-dimensional gas chromatography to sterols analysis. | 2008 Dec 19 |
|
| Androgen receptor transactivation assay using green fluorescent protein as a reporter. | 2008 Feb 15 |
|
| [Determination of endogenous anabolic steroids in hair using gas chromatography-tandem mass spectrometry]. | 2008 Jul |
|
| Testosterone doping: dealing with genetic differences in metabolism and excretion. | 2008 Jul |
|
| Factors influencing the steroid profile in doping control analysis. | 2008 Jul |
|
| 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 |
|
| 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 |
|
| Comparison of partial filling MEKC analyses of steroids with use of ESI-MS and UV spectrophotometry. | 2008 Mar |
|
| Liquid chromatographic method development for anabolic androgenic steroids using a monolithic column Application to animal feed samples. | 2008 Mar 17 |
|
| Multivariate optimization of a derivatisation procedure for the simultaneous determination of nine anabolic steroids by gas chromatography coupled with mass spectrometry. | 2008 May 9 |
|
| Simultaneous measurement of boldenone (alpha and beta), ADD, testosterone, epitestosterone and AED in bovine faeces. | 2008 Sep |
|
| Determination of urinary androgen glucuronides by capillary electrophoresis with electrospray tandem mass spectrometry. | 2009 Apr |
|
| 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 |
|
| UDP-glucuronosyltransferases (UGTs) 2B7 and UGT2B17 display converse specificity in testosterone and epitestosterone glucuronidation, whereas UGT2A1 conjugates both androgens similarly. | 2009 Feb |
|
| Evaluation of equine urine reactivity towards phase II metabolites of 17-hydroxy steroids by liquid chromatography/tandem mass spectrometry. | 2009 Jan |
|
| Physiological concentrations of anabolic steroids in human hair. | 2009 Jan 30 |
|
| Sudden unexpected death in a female fitness athlete, with a possible connection to the use of anabolic androgenic steroids (AAS) and ephedrine. | 2009 Jan 30 |
|
| [Testosterone metabolism and doping test results]. | 2009 Jan-Feb |
|
| Analysis of conjugated steroid androgens: deconjugation, derivatisation and associated issues. | 2009 Jul 12 |
|
| Substantial advantage of a combined Bayesian and genotyping approach in testosterone doping tests. | 2009 Mar |
|
| Associations among hair loss, oral sulfur-containing gases, and gastrointestinal and metabolic linked diseases in Japanese elderly men: pilot study. | 2009 Mar 13 |
|
| Effects of recombinant human LH and hCG on serum and urine LH and androgens in men. | 2009 Sep |
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
by
admin
on
Edited
Sat Jun 26 07:50:56 UTC 2021
by
admin
on
Sat Jun 26 07:50:56 UTC 2021
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| Record UNII |
48L726977Z
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| Record Status |
Validated (UNII)
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73570-4
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2235-0
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2233-5
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31030-0
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17687-5
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1646031
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10204
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481-30-1
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Epitestosterone
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DB07768
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48L726977Z
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M4949
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PRIMARY | Merck Index |
| Related Record | Type | Details | ||
|---|---|---|---|---|
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PARENT -> METABOLITE |
URINE
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| Related Record | Type | Details | ||
|---|---|---|---|---|
|
PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
