U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

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.

Originator

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

Targets

Targets

Primary TargetPharmacologyConditionPotency
860.0 nM [Ki]
29.8 nM [Ki]
1.2 µM [Ki]
Conditions
PubMed

PubMed

TitleDatePubMed
[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
Antiandrogenic activity of epitestosterone in male mice in vivo.
2001
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
Hair analysis of seven bodybuilders for anabolic steroids, ephedrine, and clenbuterol.
2002 Jan
Effects of androstenedione administration on epitestosterone metabolism in men.
2002 Jun
Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor.
2003 Oct
Hormonal profile of men with premature balding.
2004 Jan
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
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
Urinary marker of oral pregnenolone administration.
2005 Mar
Stability studies of testosterone and epitestosterone glucuronides in urine.
2006
Application of stable carbon isotope analysis to the detection of testosterone administration to cattle.
2006 Apr 19
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
Neoformation of boldenone and related steroids in faeces of veal calves.
2006 Feb
[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
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
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
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
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
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
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

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
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
on Sat Dec 16 09:02:46 GMT 2023
Edited
by admin
on Sat Dec 16 09:02:46 GMT 2023
Record UNII
48L726977Z
Record Status Validated (UNII)
Record Version
  • Download
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
Related Record Type Details
PARENT -> METABOLITE
URINE
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP