Ethisteron

Ethisterone

HCID 5284557CAS 434-03-7

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Grundinformationen

Standard-SMILES: C#C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C
InChIKey: CHNXZKVNWQUJIB-CEGNMAFCSA-N
Summenformel: C21H28O2
Durchschnittliche Molmasse: 312,4 g/mol
Monoisotopische Masse: 312,20893014

Überblick

Ethisterone is a 17beta-hydroxy steroid that is testosterone in which the 17beta hydrogen is replaced by an ethynyl group. Ethisterone was the first orally active progestin and is a metabolite of danazol. It has a role as a drug metabolite and a progestin. It is a tertiary alcohol, a 17beta-hydroxy steroid, a 3-oxo-Delta(4) steroid and a terminal acetylenic compound. It is functionally related to a testosterone.

Namen und Bezeichner

Bevorzugter Name: Ethisterone
IUPAC: (8R,9S,10R,13S,14S,17R)-17-ethynyl-17-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
Lokaler Name: Ethisteron
Englischer Name: Ethisterone
Summenformel: C21H28O2
Molmasse: 312.45

Namen und Synonyme

ethisterone434-03-7AethisteronEtisteronaNugestoralSyngestrotabsTrosinonePregneninoloneOra-LutinEthynyltestosterone17alpha-EthynyltestosteroneAethisteronum

Weitere Namen anzeigen

Progestoral17A-ETHYNYLTESTOSTERONEPronePregninGestoralNSC-9565ProdoxanProlutol

EthisteronumProgestoletsAnhydrohydroxyprogesteroneAnhydroxyprogesteroneProdroxanProduxanProgestabPranone

Datenbank-Bezeichner

CAS: 434-03-7
PubChem CID: 5284557
DTXSID: DTXSID2023016
ChEMBL: CHEMBL241694
ChEBI: CHEBI:34749
UNII: P201BVY1MJ
EC Number: 207-096-5
Nikkaji: J5.729K

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 3,5
Polarare Oberfläche (TPSA): 37,3 Å²
H-Brücken-Donoren: 1
H-Brücken-Akzeptoren: 2
Frei drehbare Bindungen: 1
Schwere Atome: 23
Formalladung: 0
Komplexität: 637

Experimentelle und physikochemische Eigenschaften

SpringerMaterials PropertiesChemical shift

Human DrugsPharmaceuticals

Endocrine DisruptorsPotential endocrine disrupting compound

Collision Cross Section180.2 Å² [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID2023016]

Physikochemische Eigenschaften

Schmelzpunkt: 263 · 263-269 °C (lit.)
Siedepunkt: 392.36 °C · 392.36°C (rough estimate)
Dichte: 1.0697 · 1.0697 (rough estimate)
Brechungsindex: 33 ° · 33 ° (C=1, Pyridine)
storage temp.: room temp
Löslichkeit: 0.05 mg/mL · Soluble to 0.05 mg/mL (0.16 mM) in DMSO
pka: 13.1 · 13.10±0.60(Predicted)
Aggregatzustand: Solid
Farbe: Light yellow to yellow
Biologische Quelle: synthetic (organic)
Wasserlöslichkeit: soluble in chloroform, DMSO (0.05 mg/ml), acetone (slightly ), ethanol (<1 mg/ml at 25°C), and water (<1 mg/ml at 25°C).
Merck: 14 · 14,3741
BRN: 1889895 · 1889895
InChI: 1S/C21H28O2/c1-4-21(23)12-9-18-16-6-5-14-13-15(22)7-10-19(14,2)17(16)8-11-20(18,21)3/h1,13,16-18,23H,5-12H2,2-3H3/t16-,17+,18+,19+,20+,21+/m1/s1
InChIKey: CHNXZKVNWQUJIB-CEGNMAFCSA-N
SMILES: C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2CC[C@@]4(C)[C@H]3CC[C@@]4(O)C#C
CAS Datenbank: 434 · 434-03-7
NIST chemische Informationen: Ethisterone(434-03-7)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Danger

H360 (95.2%): May damage fertility or the unborn child [Danger Reproductive toxicity]

P203, P280, P318, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 42 reports by companies from 5 notifications to the ECHA C&L Inventory.

Gefahrenhinweise

Regulatory InformationStatus: Active Update: 01-04-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/2184

Hazard Classes and CategoriesRepr. 1A (95.2%)

Sicherheitsdaten

wgk: 3
ridadr: UN 2811
hs_code: 29372390
RTECS-Nr.: TU5570250
risk_code: 40-48-61
hazard_code: Xn,T
safety_code: 22-24/25-45-53
Speicherklasse: 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications: Aquatic Acute 1Aquatic Chronic 1Repr. 1A

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

G - Genito urinary system and sex hormones

QG - Genito urinary system and sex hormones

Tissue LocationsKidney

Cellular LocationsCytoplasm

Verwendung und Herstellung

Use ClassificationPharmaceuticals

Anwendungen · 2 Einträge

BeschreibungEthisterone is an orally bioavailable synthetic progestin and a derivative of testosterone (Item Nos. ISO60154 | 15645) that binds to progesterone and androgen receptors (EC50s = 23 and 23.1 nM, respectively, in yeast). Ethisterone (1 μM) downregulates progesterone receptors in MCF-7 cells.

VerwendenEthisterone has been used as a component in Dulbecco′s modified eagle medium (DMEM) to culture the transfected COS-7 cell for transient transfection assay andgene transfection assay.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Prasteron Pregn-4-en-20-yn-3-one, 17-hydroxy-Pregn-4-ene-3,20-dione, 21-bromo-17-hydroxy-17-α-Pregn-5-en-20-in-3-β,17-β-diol 17-α,21-Dihydroxypregn-4-en-3,20-dion-21-acetat 3-Ethoxy-androsta-3,5-dien-17-one Androst-4-en-3,17-dion Acetylen

Nachgelagerte Produkte

17-ethyl-17-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one

Anbieter50 Anbieter

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

Shanghai Biolang Biotechnology Co., Ltd.+86-15970428662 +86-13397199602 · [email protected]

INTATRADE GmbH+49 3493/605464 · [email protected]

武汉灵灵九生物科技有限公司15623309010

Hebei shuoxi biotechnology co. LTD+8613081092107

Ergänzende Hinweise

DefinitionChEBI: A 17beta-hydroxy steroid that is testosterone in which the 17beta hydrogen is replaced by an ethynyl group. Ethisterone was the first orally active progestin and is a metabolite of danazol.