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Revision as of 17:33, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 473857222 of page 20-Hydroxyecdysone for the Chem/Drugbox validation project (updated: 'CAS_number').  Latest revision as of 06:27, 25 December 2024 edit Artoria2e5 (talk | contribs)Extended confirmed users, IP block exemptions34,319 edits →Use as supplement: move ref 
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{{Short description|Chemical compound}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{Drugbox {{Drugbox
| Verifiedfields = changed | Verifiedfields = changed
| verifiedrevid = 456500273 | verifiedrevid = 477215829
| IUPAC_name = (2β,3β,5β,22R)-2,3,14,20,22,25-Hexahydroxycholest-7-en-6-one | IUPAC_name = (2β,3β,5β,22R)-2,3,14,20,22,25-Hexahydroxycholest-7-en-6-one
| image = 20-hydroxyecdysone.png | image = 20-Hydroxyecdysone.svg
| alt = Skeletal formula of 20-hydroxyecdysone
| width = 260
| image2 = 20-Hydroxyecdysone 3D ball.png
| alt2 = Ball-and-stick model of the 20-hydroxyecdysone molecule


<!--Clinical data--> <!--Clinical data-->| tradename =
| tradename = | pregnancy_AU =
| pregnancy_AU = | pregnancy_US =
| pregnancy_US =
| pregnancy_category = X | pregnancy_category = X
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> | legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> | legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> | legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> | legal_US = ] (as a botanical substance)
| legal_status = Undetermined | legal_status =
| routes_of_administration = ] | routes_of_administration = ]


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->| bioavailability =
⚫ | protein_bound =
| bioavailability =
⚫ | metabolism = ]
⚫ | protein_bound =
⚫ | metabolism = ]
| elimination_half-life = 4-9 hours | elimination_half-life = 4-9 hours
| excretion = ]:?% | excretion = ]:?%


<!--Identifiers--> <!--Identifiers-->| CAS_number_Ref = {{cascite|changed|??}}
⚫ | CAS_number = 5289-74-7
| CAS_number_Ref = {{cascite|changed|??}}
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | CAS_number = <!-- blanked - oldvalue: 5289-74-7 -->
| UNII = 779A7KPL0Y
| ATC_prefix =
| ATC_suffix = | ATC_prefix =
| ATC_suffix =
| PubChem = 5459840 | PubChem = 5459840
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = | DrugBank =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4573597 | ChemSpiderID = 4573597
| ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 16587 | ChEBI = 16587
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 224128 | ChEMBL = 224128


<!--Chemical data--> <!--Chemical data-->| C = 27
| C=27 | H=44 | O=7 | H = 44
| O = 7
| molecular_weight = 480.63 g/mol
| smiles = O=C1\C=C3/(2(C(O)(O)C12)C)CC4(3(O)CC4(O)(C)(O)CCC(O)(C)C)C | smiles = O=C1\C=C3/(2(C(O)(O)C12)C)CC4(3(O)CC4(O)(C)(O)CCC(O)(C)C)C
⚫ | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| InChI = 1/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 | StdInChI = 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
| InChIKey = NKDFYOWSKOHCCO-YPVLXUMRBN
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
⚫ | StdInChIKey = NKDFYOWSKOHCCO-YPVLXUMRSA-N
| StdInChI = 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
⚫ | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
⚫ | StdInChIKey = NKDFYOWSKOHCCO-YPVLXUMRSA-N
}} }}

'''20-Hydroxyecdysone''' ('''ecdysterone''' or '''20E''') is a naturally occurring ] ] which controls the ] (moulting) and ] of ]. It is therefore one of the most common moulting hormones in insects, crabs, etc. A ] produced by various plants, including '']'', '']'' and '']'', its purpose is presumably to disrupt the ] and ] of insect pests. In arthropods, 20-hydroxyecdysone acts through the ]. Although mammals lack this ], 20-hydroxyecdysone affects ] biological systems. 20-Hydroxyecdysone is an ingredient of some supplements that aim to enhance physical performance. In humans, it is hypothesized to bind to the ] (ERβ) protein-coding gene.<ref>{{cite journal | vauthors = Isenmann E, Ambrosio G, Joseph JF, Mazzarino M, de la Torre X, Zimmer P, Kazlauskas R, Goebel C, Botrè F, Diel P, Parr MK | s2cid = 163166547 | display-authors = 6 | title = Ecdysteroids as non-conventional anabolic agent: performance enhancement by ecdysterone supplementation in humans | journal = Archives of Toxicology | volume = 93 | issue = 7 | pages = 1807–1816 | date = July 2019 | pmid = 31123801 | doi = 10.1007/s00204-019-02490-x | hdl-access = free | hdl = 11573/1291269 }}</ref>

==Sources in arthropods==
The primary sources of 20-hydroxyecdysone in larvae are the ], ring gland, gut, and ]. These tissues convert dietary ] into the mature forms of the hormone 20-hydroxyecdysone.<ref>{{cite journal | vauthors = Thummel CS, Chory J | title = Steroid signaling in plants and insects--common themes, different pathways | journal = Genes & Development | volume = 16 | issue = 24 | pages = 3113–29 | date = December 2002 | pmid = 12502734 | doi = 10.1101/gad.1042102 | url = http://www.genesdev.org/cgi/reprint/16/24/3113 | doi-access = free }}</ref> For the most part, these glandular tissues are lost in the adult, with exception of the fat body, which is retained as a sheath of lipid tissue surrounding the brain and organs of the abdomen. In the adult female, the ovary is a substantial source of 20-hydroxyecdysone production.<ref>{{cite journal | vauthors = Handler AM | title = Ecdysteroid titers during pupal and adult development in Drosophila melanogaster | journal = Developmental Biology | volume = 93 | issue = 1 | pages = 73–82 | date = September 1982 | pmid = 6813165 | doi = 10.1016/0012-1606(82)90240-8 }}</ref> Adult males are left with, so far as is currently known, one source of 20-hydroxyecdysone, which is the fat body tissue. These hormone-producing tissues express the ] throughout development, possibly indicating a functional ].{{cn|date=September 2024}}

==Ecdysteroid activity in arthropods==
{{unreferenced |section|date=September 2024}}
In insects, an ] is a type of ] derived from enzymatic modification of cholesterol by ] enzymes. This occurs by a mechanism similar to ] in vertebrates. ] and 20-hydroxyecdysone regulate larval molts, onset of ] formation, and ]. As these hormones are hydrophobic, they traverse ]s and permeate the tissues of an organism. Indeed, the ] is an ] ].

==In humans and other mammals==

===Use as research tool===
20-Hydroxyecdysone and other ecdysteroids are used in biochemistry research as ]s in transgenic animals, whereby a new gene is introduced into an animal so that its expression is under the control of an introduced ]. Adding or removing ecdysteroids from the animal's diet then gives a convenient way to turn the inserted gene on or off. At usual doses, 20-hydroxyecdysone appears to have little or no effect on animals that do not have extra genes inserted. Given its high oral ], therefore, it is useful for determining whether the ] has been taken up effectively.<ref>{{cite journal | vauthors = Saez E, Nelson MC, Eshelman B, Banayo E, Koder A, Cho GJ, Evans RM | title = Identification of ligands and coligands for the ecdysone-regulated gene switch | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 97 | issue = 26 | pages = 14512–7 | date = December 2000 | pmid = 11114195 | pmc = 18950 | doi = 10.1073/pnas.260499497 | url = http://www.pnas.org/cgi/reprint/97/26/14512.pdf | bibcode = 2000PNAS...9714512S | doi-access = free }}</ref> However, studies mentioned below show that 20E is not totally inert in non-transgenic mammals.

===Use as supplement===
20-Hydroxyecdysone and other ecdysteroids are marketed as ingredients in ]s for various sports, particularly ].<ref>{{cite journal | vauthors = Cohen PA, Sharfstein J, Kamugisha A, Vanhee C | title = Analysis of Ingredients of Supplements in the National Institutes of Health Supplement Database Marketed as Containing a Novel Alternative to Anabolic Steroids | journal = JAMA Network Open | volume = 3 | issue = 4 | pages = e202818 | date = April 2020 | pmid = 32293681 | doi = 10.1001/jamanetworkopen.2020.2818 | pmc = 7160690 }}</ref> Although a number of early studies supported the anabolic effects of 20-hydroxyecdysone,<ref>{{cite journal | vauthors = Simakin SY | title = The Combined Use of Ecdisten and the Product'Bodrost'during Training in Cyclical Types of Sport. | journal = Scientific Sports Bulletin | date = 1988 | pages = 2 }}</ref><ref>{{cite journal | vauthors = Gadzhieva RM, Portugalov SN, Paniushkin VV, Kondrat'eva II | title = | journal = Eksperimental'naia i Klinicheskaia Farmakologiia | date = 1995 | volume = 58 | issue = 5 | pages = 46–8 | pmid = 8704590 }}</ref><ref name="pmid18220764">{{cite journal | vauthors = Báthori M, Tóth N, Hunyadi A, Márki A, Zádor E | title = Phytoecdysteroids and anabolic-androgenic steroids--structure and effects on humans | journal = Current Medicinal Chemistry | volume = 15 | issue = 1 | pages = 75–91 | date = 2008 | pmid = 18220764 | doi = 10.2174/092986708783330674 | url = http://publicatio.bibl.u-szeged.hu/10883/1/2008_Bathori_et_al._CMC_u.pdf }}</ref><ref>{{cite report | vauthors = Smetanin BY | title = The influence of preparations of plant origin on physical work capacity. | publisher = The Russian Ministry of Public Health | date = 1986 }}</ref><ref>{{cite report | vauthors = Fadeev BG | title = Comments on the Results of Retibol in the Practice of Athletic Training and Rehabilitation | publisher = Natural Sports Research Institute }}</ref><ref name="pmid9575416">{{cite journal | vauthors = Azizov AP, Seĭfulla RD, Ankudinova IA, Kondrat'eva II, Borisova IG | title = | language = ru | journal = Eksperimental'naia i Klinicheskaia Farmakologiia | volume = 61 | issue = 1 | pages = 60–2 | date = 1998 | pmid = 9575416 }}</ref> a 2006 study concluded that the use of 30&nbsp;mg per day of 20-hydroxyecdysone administered orally did not significantly affect ] or ] responses to ], ], or training adaptations.<ref>{{cite journal | vauthors = Wilborn CD, Taylor LW, Campbell BI, Kerksick C, Rasmussen CJ, Greenwood M, Kreider RB | title = Effects of methoxyisoflavone, ecdysterone, and sulfo-polysaccharide supplementation on training adaptations in resistance-trained males | journal = Journal of the International Society of Sports Nutrition | volume = 3 | issue = 2 | pages = 19–27 | date = December 2006 | pmid = 18500969 | pmc = 2129166 | doi = 10.1186/1550-2783-3-2-19 | doi-access = free }}</ref> However, a 2019 study found significantly higher increases in ] and ] ] performance in participants dosed with ecdysterone. The study, funded by the ], demonstrated a significant ] anabolic effect.<ref>{{cite journal | vauthors = Isenmann E, Ambrosio G, Joseph JF, Mazzarino M, de la Torre X, Zimmer P, Kazlauskas R, Goebel C, Botrè F, Diel P, Parr MK | s2cid = 163166547 | display-authors = 6 | title = Ecdysteroids as non-conventional anabolic agent: performance enhancement by ecdysterone supplementation in humans | journal = Archives of Toxicology | volume = 93 | issue = 7 | pages = 1807–1816 | date = July 2019 | pmid = 31123801 | doi = 10.1007/s00204-019-02490-x | hdl-access = free | hdl = 11573/1291269 }}</ref> Other studies have elucidated the mechanism of action of 20-hydroxyecdysone on human ]s, which appears to involve relatively selective activation of ] (ERβ), known to result in ].<ref name="pmid24974955">{{cite journal | vauthors = Parr MK, Zhao P, Haupt O, Ngueu ST, Hengevoss J, Fritzemeier KH, Piechotta M, Schlörer N, Muhn P, Zheng WY, Xie MY, Diel P | title = Estrogen receptor beta is involved in skeletal muscle hypertrophy induced by the phytoecdysteroid ecdysterone | journal = Molecular Nutrition & Food Research | volume = 58 | issue = 9 | pages = 1861–72 | date = September 2014 | pmid = 24974955 | doi = 10.1002/mnfr.201300806 }}</ref>

=== Drug development ===
In 2024, the ] approved a study on the efficacy of BIO101 (20-hydroxyecdysone) in treating ], focusing on muscle strength improvement in the ]s.<ref>{{Cite web |last=Sharma |first=Soumya |date=2024-07-12 |title=FDA approves Biophytis' Phase II OBA obesity study |url=https://www.clinicaltrialsarena.com/news/us-fda-biophytis-obesity-study/ |access-date=2024-07-13 |website=Clinical Trials Arena |language=en-US}}</ref>

==External links==
* , The Ecdysone Handbook - a free online ecdysteroids database

== References ==
{{reflist}}



{{DEFAULTSORT:Hydroxyecdysone, 20-}}
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