Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C19H30O2 |
| Molecular Weight | 290.4403 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 7 / 7 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@]12CC[C@H]3[C@@H](CC[C@H]4C[C@@H](O)CC[C@]34C)[C@@H]1CCC2=O
InChI
InChIKey=QGXBDMJGAMFCBF-LUJOEAJASA-N
InChI=1S/C19H30O2/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/h12-16,20H,3-11H2,1-2H3/t12-,13-,14-,15-,16-,18-,19-/m0/s1
| Molecular Formula | C19H30O2 |
| Molecular Weight | 290.4403 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 7 / 7 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/7726568 | https://www.ncbi.nlm.nih.gov/pubmed/12054855 | https://www.ncbi.nlm.nih.gov/pubmed/15650074 | https://www.ncbi.nlm.nih.gov/pubmed/17017935
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/7726568 | https://www.ncbi.nlm.nih.gov/pubmed/12054855 | https://www.ncbi.nlm.nih.gov/pubmed/15650074 | https://www.ncbi.nlm.nih.gov/pubmed/17017935
The 17-ketosteroid epiandrosterone is a metabolite of testosterone precursor dehydroepiandrosterone (DHEA).
Epiandrosterone have been considered to be merely inactive end product of DHEA, but may in fact be physiological effectors in their own right. It is formed in peripheral tissues, from which it is released into the circulation and is ultimately excreted in the urine. Epiandrosterone is only a weak androgen, but it is widely recognized to inhibit the pentose phosphate pathway and to decrease intracellular NADPH levels. Epiandrosterone may act as a L-type Ca2+ channel antagonist. Epiandrosterone mainly transformed into 17beta-hydroxylated derivatives, 7- or 16alpha-hydroxylated metabolites under NAD(P)H conditions, and 5alpha-androstane-3,17-dione under NAD(P)+ conditions. Epiandrosterone is used as an anabolic agent (dietary supplement, a precursor to dihydrotestosterone) to increase strength, muscle hardness and also improves libido.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Determination of (13)C/(12)C ratios of endogenous urinary steroids excreted as sulpho conjugates. | 2010-11-15 |
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| Steroid degradation genes in Comamonas testosteroni TA441: Isolation of genes encoding a Δ4(5)-isomerase and 3α- and 3β-dehydrogenases and evidence for a 100 kb steroid degradation gene hot spot. | 2010-10 |
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| Effects of valproate and carbamazepine monotherapy on neuroactive steroids, their precursors and metabolites in adult men with epilepsy. | 2010-10 |
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| Determination of anabolic steroids in human urine by automated in-tube solid-phase microextraction coupled with liquid chromatography-mass spectrometry. | 2010-09-05 |
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| 16-bromoepiandrosterone, an activator of the mammalian immune system, inhibits glucose 6-phosphate dehydrogenase from Trypanosoma cruzi and is toxic to these parasites grown in culture. | 2010-07-01 |
|
| Anti-adenovirus activity of epiandrosterone and dehydroepiandrosterone derivatives. | 2010 |
|
| In vitro antiviral activity of dehydroepiandrosterone and its synthetic derivatives against vesicular stomatitis virus. | 2009-11 |
|
| Parameters for ultra-performance liquid chromatographic/tandem mass spectrometric analysis of selected androgens versus estrogens in aqueous matrices. | 2009-08-15 |
|
| Anabolic utilization of steroid hormones in Helicobacter pylori. | 2009-08 |
|
| Analysis of conjugated steroid androgens: deconjugation, derivatisation and associated issues. | 2009-07-12 |
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| Inhibition of Lassa virus glycoprotein cleavage and multicycle replication by site 1 protease-adapted alpha(1)-antitrypsin variants. | 2009-06-02 |
|
| Revealing genes associated with vitellogenesis in the liver of the zebrafish (Danio rerio) by transcriptome profiling. | 2009-03-31 |
|
| Inhibition of Trypanosoma brucei glucose-6-phosphate dehydrogenase by human steroids and their effects on the viability of cultured parasites. | 2009-03-15 |
|
| Epimerase activity of the human 11beta-hydroxysteroid dehydrogenase type 1 on 7-hydroxylated C19-steroids. | 2009-03 |
|
| A review of the current treatment methods for posthaemorrhagic hydrocephalus of infants. | 2009-01-30 |
|
| Preferential utilization of NADPH as the endogenous electron donor for NAD(P)H:quinone oxidoreductase 1 (NQO1) in intact pulmonary arterial endothelial cells. | 2009-01-01 |
|
| Diagnosis of diseases of steroid hormone production, metabolism and action. | 2009 |
|
| 7beta-Hydroxy-epiandrosterone-mediated regulation of the prostaglandin synthesis pathway in human peripheral blood monocytes. | 2008-10 |
|
| An open label, dose response study to determine the effect of a dietary supplement on dihydrotestosterone, testosterone and estradiol levels in healthy males. | 2008-08-12 |
|
| Dehydroepiandrosterone, epiandrosterone and synthetic derivatives inhibit Junin virus replication in vitro. | 2008-08 |
|
| Trace analysis of androgens and progestogens in environmental waters by ultra-performance liquid chromatography-electrospray tandem mass spectrometry. | 2008-06-27 |
|
| Isolation and identification of diglucuronides of some endogenous steroids in dogs. | 2008-02 |
|
| Hexose-6-phosphate dehydrogenase modulates 11beta-hydroxysteroid dehydrogenase type 1-dependent metabolism of 7-keto- and 7beta-hydroxy-neurosteroids. | 2007-06-27 |
|
| Effects of mutation at the D-JH junction on affinity, specificity, and idiotypy of anti-progesterone antibody DB3. | 2006-09 |
|
| Steroid hormone related male biased parasitism in chamois, Rupicapra rupicapra rupicapra. | 2006-06-15 |
|
| Hypoxia promotes relaxation of bovine coronary arteries through lowering cytosolic NADPH. | 2006-06 |
|
| Dehydroepiandrosterone and its derivatives: potentially novel anti-proliferative and chemopreventive agents. | 2006 |
|
| Role of pentose phosphate pathway-derived NADPH in hypoxic pulmonary vasoconstriction. | 2006 |
|
| Determination of sulfates of androsterone and epiandrosterone in human serum using isotope diluted liquid chromatography-electrospray ionization-mass spectrometry. | 2005-12 |
|
| Androgen metabolism via 17beta-hydroxysteroid dehydrogenase type 3 in mammalian and non-mammalian vertebrates: comparison of the human and the zebrafish enzyme. | 2005-10 |
|
| Glucuronidation of steroidal alcohols using iodosugar and imidate donors. | 2005-04-21 |
|
| Neurosteroids: metabolism in human intestine microsomes. | 2005-04 |
|
| Human liver S9 fractions: metabolism of dehydroepiandrosterone, epiandrosterone, and related 7-hydroxylated derivatives. | 2005-04 |
|
| The human cytochrome P4507B1: catalytic activity studies. | 2004-12 |
|
| Steroidogenic activities in MA-10 Leydig cells are differentially altered by cAMP and Müllerian inhibiting substance. | 2004-10 |
|
| Protection against inflammatory neurodegeneration and glial cell death by 7beta-hydroxy epiandrosterone, a novel neurosteroid. | 2004-03 |
|
| In vitro metabolism of dehydroepiandrosterone and testosterone by canine hair follicle cells. | 2004-02 |
|
| Pentose phosphate pathway coordinates multiple redox-controlled relaxing mechanisms in bovine coronary arteries. | 2003-12 |
|
| 7-Hydroxylated epiandrosterone (7-OH-EPIA) reduces ischaemia-induced neuronal damage both in vivo and in vitro. | 2003-07 |
|
| A facile and high yielding synthesis of 2,2,3,4,4-d5-androsterone-beta-D-glucuronide--an internal standard in dope. | 2003-01 |
|
| Anti-proliferative action of endogenous dehydroepiandrosterone metabolites on human cancer cell lines. | 2003-01 |
|
| Use of bioconversion for the preparation of [4-14C]-labeled 7 alpha- and 7 beta-hydroxylated derivatives of dehydroepiandrosterone and epiandrosterone. | 2002-12 |
|
| Epiandrosterone, a metabolite of testosterone precursor, blocks L-type calcium channels of ventricular myocytes and inhibits myocardial contractility. | 2002-06 |
|
| Inhibitors of pentose phosphate pathway cause vasodilation: involvement of voltage-gated potassium channels. | 2002-04 |
|
| The effect of isoflavone extract ingestion, as Trinovin, on plasma steroids in normal men. | 2002-01 |
|
| Expression and characterization of the human 3 beta-hydroxysteroid sulfotransferases (SULT2B1a and SULT2B1b). | 2001-06 |
Sample Use Guides
Epiandrosterone is used as an anabolic agent (dietary supplement). Recommended dosing is 300-400 mg for a 6-8 week cycle.
Route of Administration:
Oral
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:54:14 GMT 2025
by
admin
on
Mon Mar 31 17:54:14 GMT 2025
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| Record UNII |
8TR252Z538
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| Record Status |
Validated (UNII)
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| Record Version |
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LOINC |
2229-3
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CFR |
21 CFR 862.1430
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DSLD |
2986 (Number of products:14)
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NCI_THESAURUS |
C243
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WIKIPEDIA |
Designer-drugs-Epiandrosterone
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441302
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207-563-3
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C61747
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541975
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481-29-8
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DTXSID20289698
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300000053361
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m4934
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93996
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EPIANDROSTERONE
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8TR252Z538
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