20-HYDROXYECDYSONE

Investigational

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

Structure Search

SMILES

CC(C)(O)CC[C@@H](O)[C@](C)(O)[C@H]1CC[C@@]2(O)C3=CC(=O)[C@@H]4C[C@@H](O)[C@@H](O)C[C@]4(C)[C@H]3CC[C@]12C

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

HIDE SMILES / InChI

Molecular Formula	C27H44O7
Molecular Weight	480.6341
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	10 / 10
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18500969 | https://www.ncbi.nlm.nih.gov/pubmed/28803209 | https://www.ncbi.nlm.nih.gov/pubmed/10398339

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

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

C_max

Value	Dose	Analyte	Population
141 ng/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/37057316/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	20-HYDROXYECDYSONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
317 ng/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/37057316/	350 mg single, oral dose: 350 mg route of administration: Oral experiment type: SINGLE co-administered:	20-HYDROXYECDYSONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
399 ng/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/37057316/	700 mg single, oral dose: 700 mg route of administration: Oral experiment type: SINGLE co-administered:	20-HYDROXYECDYSONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
710 ng/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/37057316/	1400 mg single, oral dose: 1400 mg route of administration: Oral experiment type: SINGLE co-administered:	20-HYDROXYECDYSONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
346 ng/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/37057316/	350 mg 1 times / day multiple, oral dose: 350 mg route of administration: Oral experiment type: MULTIPLE co-administered:	20-HYDROXYECDYSONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
388 ng/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/37057316/	350 mg 1 times / day multiple, oral dose: 350 mg route of administration: Oral experiment type: MULTIPLE co-administered:	20-HYDROXYECDYSONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
453 ng/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/37057316/	350 mg 2 times / day multiple, oral dose: 350 mg route of administration: Oral experiment type: MULTIPLE co-administered:	20-HYDROXYECDYSONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
506 ng/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/37057316/	350 mg 2 times / day multiple, oral dose: 350 mg route of administration: Oral experiment type: MULTIPLE co-administered:	20-HYDROXYECDYSONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
524 ng/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/37057316/	450 mg 2 times / day multiple, oral dose: 450 mg route of administration: Oral experiment type: MULTIPLE co-administered:	20-HYDROXYECDYSONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
560 ng/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/37057316/	450 mg 2 times / day multiple, oral dose: 450 mg route of administration: Oral experiment type: MULTIPLE co-administered:	20-HYDROXYECDYSONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED

AUC

Value	Dose	Analyte	Population
819 ng × h/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/37057316/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	20-HYDROXYECDYSONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1927 ng × h/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/37057316/	350 mg single, oral dose: 350 mg route of administration: Oral experiment type: SINGLE co-administered:	20-HYDROXYECDYSONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
2589 ng × h/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/37057316/	700 mg single, oral dose: 700 mg route of administration: Oral experiment type: SINGLE co-administered:	20-HYDROXYECDYSONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
4097 ng × h/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/37057316/	1400 mg single, oral dose: 1400 mg route of administration: Oral experiment type: SINGLE co-administered:	20-HYDROXYECDYSONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
2141 ng × h/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/37057316/	350 mg 1 times / day multiple, oral dose: 350 mg route of administration: Oral experiment type: MULTIPLE co-administered:	20-HYDROXYECDYSONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
2389 ng × h/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/37057316/	350 mg 1 times / day multiple, oral dose: 350 mg route of administration: Oral experiment type: MULTIPLE co-administered:	20-HYDROXYECDYSONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
2234 ng × h/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/37057316/	350 mg 2 times / day multiple, oral dose: 350 mg route of administration: Oral experiment type: MULTIPLE co-administered:	20-HYDROXYECDYSONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
2768 ng × h/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/37057316/	350 mg 2 times / day multiple, oral dose: 350 mg route of administration: Oral experiment type: MULTIPLE co-administered:	20-HYDROXYECDYSONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
2429 ng × h/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/37057316/	450 mg 2 times / day multiple, oral dose: 450 mg route of administration: Oral experiment type: MULTIPLE co-administered:	20-HYDROXYECDYSONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
3203 ng × h/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/37057316/	450 mg 2 times / day multiple, oral dose: 450 mg route of administration: Oral experiment type: MULTIPLE co-administered:	20-HYDROXYECDYSONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED

T_1/2

Value	Dose	Analyte	Population
2.4 h CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/37057316/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	20-HYDROXYECDYSONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
3.26 h CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/37057316/	350 mg single, oral dose: 350 mg route of administration: Oral experiment type: SINGLE co-administered:	20-HYDROXYECDYSONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
4.85 h CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/37057316/	700 mg single, oral dose: 700 mg route of administration: Oral experiment type: SINGLE co-administered:	20-HYDROXYECDYSONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
3.84 h CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/37057316/	1400 mg single, oral dose: 1400 mg route of administration: Oral experiment type: SINGLE co-administered:	20-HYDROXYECDYSONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
4.39 h CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/37057316/	350 mg 1 times / day multiple, oral dose: 350 mg route of administration: Oral experiment type: MULTIPLE co-administered:	20-HYDROXYECDYSONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
3.39 h CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/37057316/	350 mg 1 times / day multiple, oral dose: 350 mg route of administration: Oral experiment type: MULTIPLE co-administered:	20-HYDROXYECDYSONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
3 h CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/37057316/	350 mg 2 times / day multiple, oral dose: 350 mg route of administration: Oral experiment type: MULTIPLE co-administered:	20-HYDROXYECDYSONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
3.06 h CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/37057316/	350 mg 2 times / day multiple, oral dose: 350 mg route of administration: Oral experiment type: MULTIPLE co-administered:	20-HYDROXYECDYSONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
3.72 h CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/37057316/	450 mg 2 times / day multiple, oral dose: 450 mg route of administration: Oral experiment type: MULTIPLE co-administered:	20-HYDROXYECDYSONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
2.81 h CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/37057316/	450 mg 2 times / day multiple, oral dose: 450 mg route of administration: Oral experiment type: MULTIPLE co-administered:	20-HYDROXYECDYSONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED

PubMed

Title	Date	PubMed
Steroid-triggered programmed cell death of a motoneuron is autophagic and involves structural changes in mitochondria.	2003-03-17	12561078
The effects of serotonin and ecdysone on primary sensory neurons in crayfish.	2003-02-15	12539163
11beta-Hydroxysteroid dehydrogenase type 1: tissue-specific expression and reductive metabolism of some anti-insect agent azole analogues of metyrapone.	2003-02-01	12604231
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.	2003-02	12655173
Binding mode of ecdysone agonists to the receptor: comparative modeling and docking studies.	2003-02	12638012
Synthesis and insecticidal activity of benzoheterocyclic analogues of N'-benzoyl-N-(tert-butyl)benzohydrazide: Part 1. Design of benzoheterocyclic analogues.	2003-01	12558097
Entomogenous fungus Nomuraea rileyi inhibits host insect molting by C22-oxidizing inactivation of hemolymph ecdysteroids.	2003-01	12489132
Molecular cloning and expression analysis of ultraspiracle (USP) from the rice stem borer Chilo suppressalis.	2003-01	12459199
Antioxidative and free radical scavenging effects of ecdysteroids from Serratula strangulata.	2002-12	12564645
Interactions between Spinacia oleracea and Bradysia impatiens: a role for phytoecdysteroids.	2002-12	12432520
A molt-associated chitinase cDNA from the spruce budworm, Choristoneura fumiferana.	2002-12	12429133
The orphan nuclear receptors BmE75A and BmE75C of the silkmoth Bombyx mori: hornmonal control and ovarian expression.	2002-12	12429116
Developmental profiles and ecdysone regulation of the mRNAs for two ecdysone receptor isoforms in the Mediterranean fruit fly Ceratitis capitata.	2002-12	12421413
The BmE75 nuclear receptors function as dominant repressors of the nuclear receptor BmHR3A.	2002-11-01	12200421
Molecular characterization of the insect immune protein hemolin and its high induction during embryonic diapause in the gypsy moth, Lymantria dispar.	2002-11	12530213
Ecdysteroids of Vitex scabra stem bark.	2002-11	12444704
Developmental toxicity of testosterone in the crustacean Daphnia magna involves anti-ecdysteroidal activity.	2002-11	12441123
A possible role of 20-hydroxyecdysone in embryonic development of the silkworm Bombyx mori.	2002-11	12386839
Differential expression and regulation by 20-hydroxyecdysone of mosquito ecdysteroid receptor isoforms A and B.	2002-10-31	12385823
Applying fenoxycarb at the penultimate instar triggers an additional ecdysteroid surge and induces perfect extra larval molting in the silkworm.	2002-10-01	12392697
Steroid regulation of midgut cell death during Drosophila development.	2002-10-01	12297099
Ance, a Drosophila angiotensin-converting enzyme homologue, is expressed in imaginal cells during metamorphosis and is regulated by the steroid, 20-hydroxyecdysone.	2002-10-01	12093364
A novel putative insect chitinase with multiple catalytic domains: hormonal regulation during metamorphosis.	2002-09-15	12059786
Ecdysteroids from a Zoanthus sp.	2002-08	12193031
Production of the baculovirus-expressed dengue virus glycoprotein NS1 can be improved dramatically with optimised regimes for fed-batch cultures and the addition of the insect moulting hormone, 20-Hydroxyecdysone.	2002-08	12176145
Crystal structures of ecdysteroids: the role of solvent molecules in hydrogen bonding and isostructurality.	2002-08	12149562
A protein from the cabbage looper, Trichoplusia ni, regulated by a bacterial infection is homologous to 3-dehydroecdysone 3beta-reductase.	2002-08	12110290
Induction of the early-late Ddc gene during Drosophila metamorphosis by the ecdysone receptor.	2002-06	12175493
Molecular cloning and induction of nuclear receptors from insect cell lines.	2002-06	12020840
Hormonal control of GTP cyclohydrolase I gene expression and enzyme activity during color pattern development in wings of Precis coenia.	2002-06	12020835
3-Deoxy-1beta,20-dihydroxyecdysone from the leaves of Diploclisia glaucescens.	2002-06	11996926
[Vitamin D3 and 20-hydroxyecdysone -- inhibitors of free radical lipid oxidation during D-hypervitaminosis].	2002-05-31	12035552
Reproductive and developmental effects of endocrine disrupters in invertebrates: in vitro and in vivo approaches.	2002-05-10	11988360
Ecdysone triggers the expression of Golgi genes in Drosophila imaginal discs via broad-complex.	2002-05-01	11969264
Intensity of larval diapause in the bamboo borer, Omphisa fuscidentalis.	2002-05	12130810
Existence of ionotropic glutamate receptor subtypes in cultured rat retinal ganglion cells obtained by the magnetic cell sorter method and inhibitory effects of 20-hydroxyecdysone, a neurosteroid, on the glutamate response.	2002-05	12083742
Two isoforms of the early E74 gene, an Ets transcription factor homologue, are implicated in the ecdysteroid hierarchy governing vitellogenesis of the mosquito, Aedes aegypti.	2002-04-25	11997188
Ecdysteroids and oocyte development in the black fly Simulium vittatum.	2002-04-24	12015816
Diastereomeric ecdysteroids with a cyclic hemiacetal in the side chain produced by cytochrome P450 in hormonally resistant insect cells.	2002-04-15	12054428
Phytoecdysteroid levels and distribution during development in Limnanthes alba Hartw. ex Benth. (Limnanthaceae).	2002-04-03	11926526
The expression of the let-7 small regulatory RNA is controlled by ecdysone during metamorphosis in Drosophila melanogaster.	2002-04-01	11900466
Ultrastructural changes in the corpus allatum after azadirachtin and 20-hydroxyecdysone treatment in adult females of Labidura riparia (Dermaptera).	2002-04	12165239
Spatial patterns of ecdysteroid receptor activation during the onset of Drosophila metamorphosis.	2002-04	11923209
Expression of Manduca sexta V-ATPase genes mvB, mvG and mvd is regulated by ecdysteroids.	2002-04	11919265
DNA synthesis in the imaginal wing discs of the American bollworm Helicoverpa armigera (Hübner).	2002-03	11937681
Effects of insect hormones on hemagglutination activity in two members of the Culex pipiens complex.	2002-01	11971657
Metamodulation of the biogenic amines: second-order modulation by steroid hormones and amine cocktails.	2002	12563166
[Structural diversity of ecdysteroids of Lychnis flos-cuculi].	2001-08	11862663
Comparative action of RH-0345 and pyriproxyfen on molting hormone production and protein analysis in mealworm pupae.	2001	12425065
RH-0345 restored partly the effects induced by KK-42 on reproductive events in mealworms.	2001	12425064

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 22:14:33 GMT 2025` Edited by `admin` on `Mon Mar 31 22:14:33 GMT 2025`
Record UNII	779A7KPL0Y
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BIO-101

Preferred Name

English

20-HYDROXYECDYSONE

Common Name

English

POLYPODINE C

Common Name

English

POLYPODINE A

Common Name

English

20-Hydroxyecdysone [WHO-DD]

Common Name

English

VITICOSTERONE

Common Name

English

THE-7

Common Name

English

ECDYSTEN

Common Name

English

NSC-629484

Code

English

POLYPODIN A

Common Name

English

EKDISTEN

Common Name

English

ECDYSTERONE

Common Name

English

ISOINOKOSTERONE

Common Name

English

20-HYDROXY-.ALPHA.-ECDYSONE

Common Name

English

CRUSTECDYSONE

Common Name

English

20-HYDROXYECDYSONE [MI]

Common Name

English

POLYPODIN C

Common Name

English

CHOLEST-7-EN-6-ONE, 2,3,14,20,22,25-HEXAHYDROXY-, (2.BETA.,3.BETA.,5.BETA.,22R)-

Systematic Name

English

COMMISTERONE

Common Name

English

CRUSTECDYSON

Common Name

English

BIO101

Code

English

ECDYSTERON

Common Name

English

BIO 101 [WHO-DD]

Common Name

English

Classification Tree Code System Code

EU-Orphan Drug

EU/3/18/2030