Editing 20-Hydroxyecdysone (section)

{{Short description|Chemical compound}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Drugbox
| Verifiedfields     = changed
| verifiedrevid      = 477215829
| IUPAC_name         = (2β,3β,5β,22R)-2,3,14,20,22,25-Hexahydroxycholest-7-en-6-one
| 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-->
| tradename          = 
| pregnancy_AU       = 
| pregnancy_US       = 
| pregnancy_category = X
| legal_AU           = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
| legal_CA           = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK           = <!-- GSL, P, POM, CD, or Class A, B, C -->
| legal_US           = [[Dietary supplement]] (as a botanical substance)
| legal_status       = 
| routes_of_administration = [[Mouth|Oral]]

<!--Pharmacokinetic data-->
| bioavailability    = 
| protein_bound      = 
| metabolism         = [[Liver|Hepatic]]
| elimination_half-life = 4-9 hours
| excretion          = [[Urine|Urinary]]:?%

<!--Identifiers-->
| synonyms           = BIO101
| CAS_number_Ref     = {{cascite|changed|??}}
| CAS_number         = 5289-74-7
| UNII_Ref           = {{fdacite|correct|FDA}}
| UNII               = 779A7KPL0Y
| ATC_prefix         = 
| ATC_suffix         = 
| PubChem            = 5459840
| DrugBank_Ref       = {{drugbankcite|correct|drugbank}}
| DrugBank           = 
| ChemSpiderID_Ref   = {{chemspidercite|correct|chemspider}}
| ChemSpiderID       = 4573597
| ChEBI_Ref          = {{ebicite|correct|EBI}}
| ChEBI              = 16587
| ChEMBL_Ref         = {{ebicite|correct|EBI}}
| ChEMBL             = 224128

<!--Chemical data-->
| C                  = 27
| H                  = 44
| O                  = 7
| smiles             = O=C1\C=C3/[C@@H]([C@]2(C[C@H](O)[C@H](O)C[C@@H]12)C)CC[C@]4([C@@]3(O)CC[C@@H]4[C@](O)(C)[C@H](O)CCC(O)(C)C)C
| StdInChI_Ref       = {{stdinchicite|correct|chemspider}}
| 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 [[ecdysteroid]] [[hormone]] which controls the [[ecdysis]] (moulting) and [[metamorphosis]] of [[arthropods]]. It is therefore one of the most common moulting hormones in insects, crabs, etc. A [[phytoecdysteroid]] produced by various plants, including ''[[Cyanotis|Cyanotis vaga]]'', ''[[Ajuga turkestanica]]'' and ''[[Rhaponticum carthamoides]]'', its purpose is presumably to disrupt the [[developmental biology|development]] and [[reproduction]] of insect pests. In arthropods, 20-hydroxyecdysone acts through the [[ecdysone receptor]]. Although mammals lack this [[Receptor (biochemistry)|receptor]], 20-hydroxyecdysone affects [[mammalian]] 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 [[estrogen receptor beta]] (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 | 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 | bibcode = 2019ArTox..93.1807I | hdl-access = free | hdl = 11573/1291269 }}</ref>