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
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CC[C@@]4([H])C[C@@H](O)CC[C@]34C
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
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 |
|---|---|---|
| Expression and characterization of the human 3 beta-hydroxysteroid sulfotransferases (SULT2B1a and SULT2B1b). | 2001 Jun |
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| The effect of isoflavone extract ingestion, as Trinovin, on plasma steroids in normal men. | 2002 Jan |
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| A facile and high yielding synthesis of 2,2,3,4,4-d5-androsterone-beta-D-glucuronide--an internal standard in dope. | 2003 Jan |
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| 7-Hydroxylated epiandrosterone (7-OH-EPIA) reduces ischaemia-induced neuronal damage both in vivo and in vitro. | 2003 Jul |
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| The human cytochrome P4507B1: catalytic activity studies. | 2004 Dec |
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| In vitro metabolism of dehydroepiandrosterone and testosterone by canine hair follicle cells. | 2004 Feb |
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| Neurosteroids: metabolism in human intestine microsomes. | 2005 Apr |
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| Human liver S9 fractions: metabolism of dehydroepiandrosterone, epiandrosterone, and related 7-hydroxylated derivatives. | 2005 Apr |
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| Androgen metabolism via 17beta-hydroxysteroid dehydrogenase type 3 in mammalian and non-mammalian vertebrates: comparison of the human and the zebrafish enzyme. | 2005 Oct |
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| Dehydroepiandrosterone and its derivatives: potentially novel anti-proliferative and chemopreventive agents. | 2006 |
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| Role of pentose phosphate pathway-derived NADPH in hypoxic pulmonary vasoconstriction. | 2006 |
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| Hypoxia promotes relaxation of bovine coronary arteries through lowering cytosolic NADPH. | 2006 Jun |
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| Steroid hormone related male biased parasitism in chamois, Rupicapra rupicapra rupicapra. | 2006 Jun 15 |
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| Hexose-6-phosphate dehydrogenase modulates 11beta-hydroxysteroid dehydrogenase type 1-dependent metabolism of 7-keto- and 7beta-hydroxy-neurosteroids. | 2007 Jun 27 |
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| Dehydroepiandrosterone, epiandrosterone and synthetic derivatives inhibit Junin virus replication in vitro. | 2008 Aug |
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| Isolation and identification of diglucuronides of some endogenous steroids in dogs. | 2008 Feb |
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| Trace analysis of androgens and progestogens in environmental waters by ultra-performance liquid chromatography-electrospray tandem mass spectrometry. | 2008 Jun 27 |
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| 7beta-Hydroxy-epiandrosterone-mediated regulation of the prostaglandin synthesis pathway in human peripheral blood monocytes. | 2008 Oct |
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| Anabolic utilization of steroid hormones in Helicobacter pylori. | 2009 Aug |
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| A review of the current treatment methods for posthaemorrhagic hydrocephalus of infants. | 2009 Jan 30 |
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| Inhibition of Trypanosoma brucei glucose-6-phosphate dehydrogenase by human steroids and their effects on the viability of cultured parasites. | 2009 Mar 15 |
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| In vitro antiviral activity of dehydroepiandrosterone and its synthetic derivatives against vesicular stomatitis virus. | 2009 Nov |
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| Anti-adenovirus activity of epiandrosterone and dehydroepiandrosterone derivatives. | 2010 |
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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 Oct |
|
| Effects of valproate and carbamazepine monotherapy on neuroactive steroids, their precursors and metabolites in adult men with epilepsy. | 2010 Oct |
|
| Determination of anabolic steroids in human urine by automated in-tube solid-phase microextraction coupled with liquid chromatography-mass spectrometry. | 2010 Sep 5 |
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
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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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m4934
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93996
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EPIANDROSTERONE
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8TR252Z538
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SUBSTANCE RECORD
