Basic information
- 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- Molecular formula
- C21H28O2
- Average molar mass
- 312.4 g/mol
- Monoisotopic mass
- 312.20893014
Overview
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.
Names & identifiers
- Preferred 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
- English name
- Ethisterone
- Molecular formula
- C21H28O2
- Molecular weight
- 312.45
Names & synonyms
ethisterone434-03-7AethisteronEtisteronaNugestoralSyngestrotabsTrosinonePregneninoloneOra-LutinEthynyltestosterone17alpha-EthynyltestosteroneAethisteronum
Show more names
Progestoral17A-ETHYNYLTESTOSTERONEPronePregninGestoralNSC-9565ProdoxanProlutol
EthisteronumProgestoletsAnhydrohydroxyprogesteroneAnhydroxyprogesteroneProdroxanProduxanProgestabPranone
Database identifiers
- CAS
434-03-7- PubChem CID
- 5284557
- DTXSID
DTXSID2023016- ChEMBL
CHEMBL241694- ChEBI
CHEBI:34749- UNII
- P201BVY1MJ
- EC Number
- 207-096-5
- Nikkaji
- J5.729K
Properties
Computed structural properties
- XLogP
- 3.5
- Topological polar surface area
- 37.3 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 1
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 637
Experimental & physicochemical properties
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]
Physicochemical properties
- Melting point
- 263 · 263-269 °C (lit.)
- Boiling point
- 392.36 °C · 392.36°C (rough estimate)
- alpha
- 23 · D23 +23.8° (dioxane); D25 -32.0° (pyridine)
- Density
- 1.0697 · 1.0697 (rough estimate)
- refractive index
- 33 ° · 33 ° (C=1, Pyridine)
- storage temp.
- room temp
- solubility
- 0.05 mg/mL · Soluble to 0.05 mg/mL (0.16 mM) in DMSO
- pka
- 13.1 · 13.10±0.60(Predicted)
- form
- Solid
- color
- Light yellow to yellow
- biological source
- synthetic (organic)
- Water Solubility
- 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 DataBase Reference
- 434 · 434-03-7
- FDA UNII
- 201 BVY1MJ · P201BVY1MJ
- ATC code
- 3 DC04 · G03DC04
- NIST Chemistry Reference
- Ethisterone(434-03-7)
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 8 · GHS08,GHS09
- Signal word
- Danger
- Hazard statements
- 360 FD-H410 · H360FD-H410
- Precautionary statements
- 201 · P201-P202-P273-P280-P308+P313-P391
- PPE
- 3 · Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
- Hazard Codes
- Xn,T
- Risk Statements
- 40 · 40-48-61
- Safety Statements
- 22 · 22-24/25-45-53
- RIDADR
- 2811 · UN 2811
- WGK Germany
- 3 · 3
- RTECS
- 5570250 · TU5570250
- HS Code
- 29372390 · 29372390
- Storage Class
- 6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard Classifications
- 1 Aquatic · Aquatic Acute 1Aquatic Chronic 1Repr. 1A
- REACH Registrations
- Active
Safety & regulation
GHS classification
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.
Hazard information
Regulatory InformationStatus: Active Update: 01-04-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/2184
Hazard Classes and CategoriesRepr. 1A (95.2%)
Safety data
- PPE
- Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
- wgk
- 3
- rtecs
- TU5570250
- ridadr
- UN 2811
- hs_code
- 29372390
- risk_code
- 40-48-61
- Signal word
- Danger
- Symbol(GHS)
- GHS08,GHS09
- hazard_code
- Xn,T
- safety_code
- 22-24/25-45-53
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard statements
- H360FD-H410
- REACH Registrations
- Active
- Hazard Classifications
- Aquatic Acute 1Aquatic Chronic 1Repr. 1A
- Precautionary statements
- P201-P202-P273-P280-P308+P313-P391
Chemistry & industry
Pharmacology
ATC Code
G - Genito urinary system and sex hormones
QG - Genito urinary system and sex hormones
Tissue LocationsKidney
Cellular LocationsCytoplasm
Uses & manufacturing
Use ClassificationPharmaceuticals
Applications
DescriptionEthisterone 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.
UsesEthisterone 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.
UsesSynthetic progestogen; metabolite of Danazol; intermediate in the synthesis of Spironolactone
General DescriptionEthisterone is aprogestogen. It is a danazol derivative.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
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
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
上海弘顺生物科技有限公司15901914505 · [email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
北京华威锐科化工有限公司0757-86329057 18934348241 · [email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
太原市瑞和丰科贸有限公司+86 351 7031519 · [email protected]
安耐吉化学&3A（安徽泽升科技股份有限公司）400-0056266 · [email protected]
MedBio脉铂医药021-69568360 18916172912 · [email protected]
上海钰康生物科技有限公司+86-18930848214 +86-021-56762820 · [email protected]
Xiamen AmoyChem Co., Ltd+86-86-5926051114 · [email protected]
Hebei Qige Biological Technology Co. Ltd+86 +8618733132031
斯百全化学（上海）有限公司021-021-021-67601398-809-809-809 15221380277 · [email protected]
上海思域化工科技有限公司86-21-34053660 · [email protected]
AdooQ BioScience, LLC+1 (866) 930-6790 · [email protected]
Wuhan NCE Biomedical Co.,Ltd.4000-027-021 |24 +86-13986109188 | +86-15623472865 | +81-08033611988
TCI AMERICA800-4238616 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
TCI Europe320-37350700 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
潍坊沃腾进出口有限公司0536-2456718
南京生利德生物科技有限公司025-57798810 18652991625 · [email protected]
湖北鑫源顺医药化工有限公司13971561712, 13995564702, 027-50664929 · [email protected]
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
上海将来实业股份有限公司021-61552785 · [email protected]
上海笛柏生物科技有限公司400-008-9730,021-54359730 400-008-9730 · [email protected]
成都零六生物科技有限公司400-1166-196 13458535857 · [email protected]
上海御略医药科技有限公司021-60345187 13671753212 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
杭州杰恒化工有限公司0571-87396432 · [email protected]
江苏艾康生物医药研发有限公司025-66028182 17714375163 · [email protected]
南京百鑫德诺生物科技有限公司025-58849295 · [email protected]
上海孚一生物科技有限公司+86 (21) 61124340
凯试（上海）科技有限公司021-50135380 · [email protected]
池州凯隆进出口贸易有限公司[email protected]
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
石家庄通洋进出口有限公司[email protected]
Wuhan Biocar Bio-Pharm Co., Ltd.86 15387057351 · [email protected]
TargetMol中国（陶术生物）021-021-33632979 15002134094 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
上海波以尔化工有限公司021-50182298 021-50180596 · [email protected]
九鼎化学（上海）科技有限公司4009209199 · [email protected]
BOC Sciences16314854226; +8616314854226 · [email protected]
武汉鑫儒化工有限公司15927387915 15337108568
厦门志信化学有限公司+86-5922680277 +86-13806087780 · [email protected]
泰安嘉岳生物化工有限公司15318151873 · [email protected]
Additional notes
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.
Related reactions
5 records
Compound notes
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