Ethisteron
Ethisterone
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Grundinformationen
- CAS
434-03-7- 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
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- XLogP
- 3,5
- Polarare Oberfläche (TPSA)
- 37,3 Ų
- 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 Ų [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)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
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
G - Genito urinary system and sex hormones
QG - Genito urinary system and sex hormones
Tissue LocationsKidney
Cellular LocationsCytoplasm
Verwendung und Herstellung
Use ClassificationPharmaceuticals
Anwendungen
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.
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