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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
Structure of EPITESTOSTERONE

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

HIDE SMILES / InChI

Description

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.

Originator

Clark, L.C.|Kochakian, C.D.
1
Curator's Comment: Clark and Kochakian reported epitestosterone for the first time in 1947 as an androgen metabolite on incubation with rabbit liver slices. reference retireved from https://www.ncbi.nlm.nih.gov/pubmed/14630088

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Binding Agent
1064
 860.0 nM [Ki]
Binding Agent
1064
 29.8 nM [Ki]
Inhibitor
8297
 1.2 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Approved
8429
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
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
Alternative methodology for the analysis of progesterone, testosterone, and epi-testosterone in bovine liver and veal muscle.
2006 Mar-Apr
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
Bayesian detection of abnormal values in longitudinal biomarkers with an application to T/E ratio.
2007 Apr
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
Evaluation of boldenone formation and related steroids transformations in veal faeces by liquid chromatography/tandem mass spectrometry.
2008
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
Urinary androgens and cortisol metabolites in field-sampled bonobos (Pan paniscus).
2008 Feb 1
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
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
Doping test results dependent on genotype of uridine diphospho-glucuronosyl transferase 2B17, the major enzyme for testosterone glucuronidation.
2008 Jul
Isolation and quantification by high-performance liquid chromatography-ion-trap mass spectrometry of androgen sulfoconjugates in human urine.
2008 Jul 4
Genetic aspects of epitestosterone formation and androgen disposition: influence of polymorphisms in CYP17 and UGT2B enzymes.
2008 Jun
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
Direct quantification of steroid glucuronides in human urine by liquid chromatography-electrospray tandem mass spectrometry.
2008 Mar 7
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

Patents

WO2002087552
1

Sample Use Guides

In Vivo Use Guide
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
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.
Name Type Language
EPITESTOSTERONE
MI  
Common Name English
17.ALPHA.-CIS-TESTOSTERONE
Common Name English
ISOTESTOSTERONE
Common Name English
17.ALPHA.-TESTOSTERONE
Systematic Name English
17.ALPHA.-HYDROXYANDROST-4-EN-3-ONE
Systematic Name English
CIS-TESTOSTERONE
Common Name English
EPITESTOSTERONE [MI]
Common Name English
TESTOSTERONE RELATED COMPOUND C [USP-RS]
Common Name English
NSC-26499
Code English
TESTOSTERONE IMPURITY C [EP IMPURITY]
Common Name English
4-ANDROSTENE-17.ALPHA.-OL-3-ONE
Common Name English
ANDROST-4-EN-17.ALPHA.-OL-3-ONE
Common Name English
Classification Tree Code System Code
LOINC 73570-4
Created by admin on Sat Dec 16 09:02:46 GMT 2023 , Edited by admin on Sat Dec 16 09:02:46 GMT 2023
LOINC 2235-0
Created by admin on Sat Dec 16 09:02:46 GMT 2023 , Edited by admin on Sat Dec 16 09:02:46 GMT 2023
LOINC 2233-5
Created by admin on Sat Dec 16 09:02:46 GMT 2023 , Edited by admin on Sat Dec 16 09:02:46 GMT 2023
LOINC 2234-3
Created by admin on Sat Dec 16 09:02:46 GMT 2023 , Edited by admin on Sat Dec 16 09:02:46 GMT 2023
LOINC 31030-0
Created by admin on Sat Dec 16 09:02:46 GMT 2023 , Edited by admin on Sat Dec 16 09:02:46 GMT 2023
LOINC 17687-5
Created by admin on Sat Dec 16 09:02:46 GMT 2023 , Edited by admin on Sat Dec 16 09:02:46 GMT 2023
Code System Code Type Description
NSC
26499
Created by admin on Sat Dec 16 09:02:46 GMT 2023 , Edited by admin on Sat Dec 16 09:02:46 GMT 2023
PRIMARY
PUBCHEM
10204
Created by admin on Sat Dec 16 09:02:46 GMT 2023 , Edited by admin on Sat Dec 16 09:02:46 GMT 2023
PRIMARY
EPA CompTox
DTXSID8022329
Created by admin on Sat Dec 16 09:02:46 GMT 2023 , Edited by admin on Sat Dec 16 09:02:46 GMT 2023
PRIMARY
WIKIPEDIA
Epitestosterone
Created by admin on Sat Dec 16 09:02:46 GMT 2023 , Edited by admin on Sat Dec 16 09:02:46 GMT 2023
PRIMARY
CAS
481-30-1
Created by admin on Sat Dec 16 09:02:46 GMT 2023 , Edited by admin on Sat Dec 16 09:02:46 GMT 2023
PRIMARY
RS_ITEM_NUM
1646031
Created by admin on Sat Dec 16 09:02:46 GMT 2023 , Edited by admin on Sat Dec 16 09:02:46 GMT 2023
PRIMARY
DRUG BANK
DB07768
Created by admin on Sat Dec 16 09:02:46 GMT 2023 , Edited by admin on Sat Dec 16 09:02:46 GMT 2023
PRIMARY
FDA UNII
48L726977Z
Created by admin on Sat Dec 16 09:02:46 GMT 2023 , Edited by admin on Sat Dec 16 09:02:46 GMT 2023
PRIMARY
MERCK INDEX
m4949
Created by admin on Sat Dec 16 09:02:46 GMT 2023 , Edited by admin on Sat Dec 16 09:02:46 GMT 2023
PRIMARY Merck Index
CHEBI
42534
Created by admin on Sat Dec 16 09:02:46 GMT 2023 , Edited by admin on Sat Dec 16 09:02:46 GMT 2023
PRIMARY
PARENT (METABOLITE)
Structure of ANDROSTENEDIONE
SUBSTANCE RECORD
Structure of EPITESTOSTERONE
NIH
NCATS
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