Epitestosterone
The 17-alpha isomer of testosterone, derived from pregnenolone via the delta5-steroid pathway, and via 5-androstene-3-beta,17-alpha-diol. Epitestosterone acts as an antiandrogen in various target tissues. The ratio between testosterone/epitestosterone is used to monitor anabolic drug abuse.
Structure for HMDB00628 (Epitestosterone)
C19H28O2
288.4244
288.20893014
(1S,2R,10R,11S,14R,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
epitestosterone
481-30-1
MUMGGOZAMZWBJJ-KZYORJDKSA-N
This compound belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of mascliine characteristics. They also show profound effects on scalp and body hair in humans.
Organic compounds
Lipids and lipid-like moleclies
Steroids and steroid derivatives
Androstane steroids
Androgens and derivatives
Aliphatic homopolycyclic compounds
Detected and Quantified
Solid
LC-MS/MS Spectrum – Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0090000000-e1af5f6bcaf571731a2bView in MoNA
LC-MS/MS Spectrum – Quattro_QQQ 25V, Positive (Annotated)splash10-052b-7900000000-581eb9c19ccb29ebac52View in MoNA
LC-MS/MS Spectrum – Quattro_QQQ 40V, Positive (Annotated)splash10-052b-9300000000-37c235bd069ce0c93813View in MoNA
LC-MS/MS Spectrum – Linear Ion Trap , positivesplash10-0fk9-1690000000-b39908a52b06c7853085View in MoNA
1H NMR SpectrumNot Available
[1H,13C] 2D NMR SpectrumNot Available
Not Available
- Kicman AT, Coutts SB, Cowan DA, Handelsman DJ, Howe CJ, Burring S, Wu FC: Adrenal and gonadal contributions to urinary excretion and plasma concentration of epitestosterone in men–effect of adrenal stimliation and implications for detection of testosterone abuse. Clin Endocrinol (Oxf). 1999 May;50(5):661-8. [PubMed:10468933 ]
Not Available
Not Available
Not Available
Not Available
FDB021799
Not Available
9789
Not Available
Not Available
Not Available
Epitestosterone
HMDB00628
HMDB00628
5601
10204
FFA
Not Available
- Falk O, Palonek E, Bjorkhem I: Effect of ethanol on the ratio between testosterone and epitestosterone in urine. Clin Chem. 1988 Jul;34(7):1462-4. [PubMed:3390919 ]
- Kicman AT, Oftebro H, Walker C, Norman N, Cowan DA: Potential use of ketoconazole in a dynamic endocrine test to differentiate between biological outliers and testosterone use by athletes. Clin Chem. 1993 Sep;39(9):1798-803. [PubMed:8375050 ]
- Riondino G, Strollo F: [Age-dependent changes in epitestosterone urinary excretion in man]. Boll Soc Ital Biol Sper. 1981 Nov 30;57(22):2215-21. [PubMed:7326107 ]
- Starka L: Epitestosterone. J Steroid Biochem Mol Biol. 2003 Oct;87(1):27-34. [PubMed:14630088 ]
- Marenich LP: [Effect of chorionic gonadotropin on the urinary excretion of testosterone and other androgens in healthy men and those with coronary arteriosclerosis]. Kardiologiia. 1979 Jun;19(6):76-9. [PubMed:156806 ]
- Aguilera R, Hatton CK, Catlin DH: Detection of epitestosterone doping by isotope ratio mass spectrometry. Clin Chem. 2002;48(4):629-36. [PubMed:11901061 ]
- Bicikova M, Hampl R, Hill M, Starka L: Inhibition of steroid 17 alpha-hydroxylase and C17,20-lyase in the human testis by epitestosterone. J Steroid Biochem Mol Biol. 1993 Oct;46(4):515-8. [PubMed:8217882 ]
- Havlikova H, Hill M, Hampl R, Starka L: Sex- and age-related changes in epitestosterone in relation to pregnenolone sulfate and testosterone in normal subjects. J Clin Endocrinol Metab. 2002 May;87(5):2225-31. [PubMed:11994368 ]
- Yamamoto Y, Peric-Golia P, Osawa Y, Kirdani RY, Sanberg AA: Androgen metabolism in sheep. Steroids. 1978 Oct;32(3):373-88. [PubMed:715826 ]
- Kicman AT, Coutts SB, Cowan DA, Handelsman DJ, Howe CJ, Burring S, Wu FC: Adrenal and gonadal contributions to urinary excretion and plasma concentration of epitestosterone in men–effect of adrenal stimulation and implications for detection of testosterone abuse. Clin Endocrinol (Oxf). 1999 May;50(5):661-8. [PubMed:10468933 ]