Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C27H44O7 |
| Molecular Weight | 480.6341 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 10 / 10 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]1(CC[C@@]2(O)C3=CC(=O)[C@]4([H])C[C@@H](O)[C@@H](O)C[C@]4(C)[C@@]3([H])CC[C@]12C)[C@@](C)(O)[C@H](O)CCC(C)(C)O
InChI
InChIKey=NKDFYOWSKOHCCO-YPVLXUMRSA-N
InChI=1S/C27H44O7/c1-23(2,32)9-8-22(31)26(5,33)21-7-11-27(34)16-12-18(28)17-13-19(29)20(30)14-24(17,3)15(16)6-10-25(21,27)4/h12,15,17,19-22,29-34H,6-11,13-14H2,1-5H3/t15-,17-,19+,20-,21-,22+,24+,25+,26+,27+/m0/s1
20-Hydroxyecdysone is a naturally occurring ecdysteroid hormone, which is marketed as dietary supplements that can increase strength and muscle mass during resistance training, particularly bodybuilding. It was found, that 20-hydroxyecdysone did not affect body composition or training adaptations nor did they influence the anabolic/catabolic hormone status or general markers of catabolism in resistance-trained males. Because is known, that ecdysteroids have been shown to prevent various changes in mammalian tissues after female sex hormone deprivation. 20-Hydroxyecdysone also was investigated on these properties. It was found in rats, that 20-Hydroxyecdysone had a beneficial effect on reducing blood pressure and consequently preventing dilated cardiac hypertrophy. Some in vitro experiments showed, that 20-hydroxyecdysone had effects on lymphocytes and neutrophils, and may act as an immunomodulator.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Regulation of transcription factors MHR4 and betaFTZ-F1 by 20-hydroxyecdysone during a larval molt in the tobacco hornworm, Manduca sexta. | 2001 Apr 1 |
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| Induction of DNA synthesis by 20-hydroxyecdysone in the prothoracic gland cells of the silkworm Bombyx mori during the last larval instar. | 2001 Dec |
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| The chemical and biological properties of methoxyfenozide, a new insecticidal ecdysteroid agonist. | 2001 Feb |
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| The vitellogenin gene of the mosquito Aedes aegypti is a direct target of ecdysteroid receptor. | 2001 Feb 28 |
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| Isolation and expression of the ecdysteroid-inducible angiotensin-converting enzyme-related gene in wing discs of Bombyx mori. | 2001 Jan |
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| Identification and ecdysteroid antagonist activity of three oligostilbenes from the seeds of Carex pendula (Cyperaceae). | 2001 Jun |
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| Ecdysteroids from two Brazilian Vitex species. | 2001 Mar |
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| Significance of absorption, oxidation, and binding to toxicity of four ecdysone agonists in multi-resistant cotton leafworm. | 2001 Mar |
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| 20-hydroxyecdysone causes increased aggressiveness in female American lobsters, Homarus americanus. | 2001 Mar |
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| Glue secretion in the Drosophila salivary gland: a model for steroid-regulated exocytosis. | 2001 Mar 1 |
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| Hormonal regulation and patterning of the broad-complex in the epidermis and wing discs of the tobacco hornworm, Manduca sexta. | 2001 Mar 1 |
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| Spectroscopic characterisation and identification of ecdysteroids using high-performance liquid chromatography combined with on-line UV--diode array, FT-infrared and 1H-nuclear magnetic resonance spectroscopy and time of flight mass spectrometry. | 2001 Mar 2 |
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| Interactions between the inositol 1,4,5-trisphosphate and cyclic AMP signaling pathways regulate larval molting in Drosophila. | 2001 May |
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| [Vitamin D3 and 20-hydroxyecdysone -- inhibitors of free radical lipid oxidation during D-hypervitaminosis]. | 2001 May-Jun |
|
| Isolation and expression of an ecdysteroid-inducible neutral endopeptidase 24.11-like gene in wing discs of Bombyx mori. | 2001 Nov 1 |
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| Dual ecdysteroid action on the epitracheal glands and central nervous system preceding ecdysis of Manduca sexta. | 2001 Oct |
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| Periodic expression of an ecdysteroid-induced nuclear receptor in a lepidopteran cell line (IAL-PID2). | 2001 Oct |
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| Antisense expression of the 20-hydroxyecdysone receptor (EcR) in transfected mosquito cells uncovers a new EcR isoform that varies at the C-terminal end. | 2001 Sep |
|
| Metamodulation of the biogenic amines: second-order modulation by steroid hormones and amine cocktails. | 2002 |
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| Expression of Manduca sexta V-ATPase genes mvB, mvG and mvd is regulated by ecdysteroids. | 2002 Apr |
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| The expression of the let-7 small regulatory RNA is controlled by ecdysone during metamorphosis in Drosophila melanogaster. | 2002 Apr 1 |
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| Ecdysteroids from a Zoanthus sp. | 2002 Aug |
|
| Crystal structures of ecdysteroids: the role of solvent molecules in hydrogen bonding and isostructurality. | 2002 Aug |
|
| Interactions between Spinacia oleracea and Bradysia impatiens: a role for phytoecdysteroids. | 2002 Dec |
|
| Biological activities of a specific ecdysteroid dimer and of selected monomeric structural analogues in the B(II) bioassay. | 2002 Feb |
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| Phytoecdysteroids from the juice of Serratula coronata L. (Asteraceae). | 2002 Feb |
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| Ecdysone-regulated puff genes 2000. | 2002 Feb |
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| The induction of DNA puff BhC4-1 gene is a late response to the increase in 20-hydroxyecdysone titers in last instar dipteran larvae. | 2002 Jan |
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| Hormonal control of GTP cyclohydrolase I gene expression and enzyme activity during color pattern development in wings of Precis coenia. | 2002 Jun |
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| DNA synthesis in the imaginal wing discs of the American bollworm Helicoverpa armigera (Hübner). | 2002 Mar |
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| Intensity of larval diapause in the bamboo borer, Omphisa fuscidentalis. | 2002 May |
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| Molecular characterization of the insect immune protein hemolin and its high induction during embryonic diapause in the gypsy moth, Lymantria dispar. | 2002 Nov |
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| A possible role of 20-hydroxyecdysone in embryonic development of the silkworm Bombyx mori. | 2002 Nov |
|
| Ance, a Drosophila angiotensin-converting enzyme homologue, is expressed in imaginal cells during metamorphosis and is regulated by the steroid, 20-hydroxyecdysone. | 2002 Oct 1 |
|
| A novel putative insect chitinase with multiple catalytic domains: hormonal regulation during metamorphosis. | 2002 Sep 15 |
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| Effects of 20-hydroxyecdysone and serotonin on neurite growth and survival rate of antennal lobe neurons in pupal stage of the silk moth Bombyx mori in vitro. | 2003 Feb |
|
| Synthesis and insecticidal activity of benzoheterocyclic analogues of N'-benzoyl-N-(tert-butyl)benzohydrazide: Part 1. Design of benzoheterocyclic analogues. | 2003 Jan |
|
| Molecular cloning and expression analysis of ultraspiracle (USP) from the rice stem borer Chilo suppressalis. | 2003 Jan |
|
| Steroid-triggered programmed cell death of a motoneuron is autophagic and involves structural changes in mitochondria. | 2003 Mar 17 |
Sample Use Guides
200 mg of 20-hydroxyecdysone for 8-weeks during training. At 0, 4, and 8-weeks, subjects donated fasting blood samples and completed comprehensive muscular strength, muscular endurance, anaerobic capacity, and body composition.
Route of Administration:
Oral
20-hydroxyecdysone (1 microM) was found to activate in vitro T-cell CD2 presentation, which is suppressed both in secondary immunodeficient persons and pharmacologically by increasing intracellular cAMP levels. In addition, 20-hydroxyecdysone (1 microM) was also revealed to modulate the fluoride-stimulated respiratory burst of human neutrophils in the same manner as water soluble antioxidants.
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| Classification Tree | Code System | Code | ||
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EU-Orphan Drug |
EU/3/18/2030
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DSLD |
1581 (Number of products:12)
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FDA ORPHAN DRUG |
639318
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16587
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5459840
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ecdysterone
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DTXSID5040388
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629484
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100000178051
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779A7KPL0Y
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m4808
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20-Hydroxyecdysone
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5289-74-7
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ACTIVE MOIETY
