Etonogestrel

Base Information

• Chemical Name: Etonogestrel
• CAS No.: 54048-10-1
• Deprecated CAS: 165050-21-5
• Molecular Formula: C22H28O2
• Molecular Weight: 324.463
• Hs Code.: 2937230000
• European Community (EC) Number: 258-936-2
• UNII: 304GTH6RNH
• DSSTox Substance ID: DTXSID9046782
• Nikkaji Number: J76.212A
• Wikipedia: Etonogestrel
• Wikidata: Q3733839
• NCI Thesaurus Code: C47528
• RXCUI: 14584
• Pharos Ligand ID: 1L78CHDF9QDD
• Metabolomics Workbench ID: 42683
• ChEMBL ID: CHEMBL1531
• Mol file: 54048-10-1.mol

Synonyms:13-ethyl-17-hydroxy-11-methylene-18,19-dinor-17alpha-pregn-4-en-20-yn-3-one;18,19-dinorpregn-4-en-20-yn-3-one, 13-ethyl-17-hydroxy-11-methylene-, (17-alpha)-;3-keto-desogestrel;3-ketodesogestrel;3-oxo desogestrel;3-oxodesogestrel;etonogestrel;Implanon;nexplanon;ORG-3236

Chemical Property of Etonogestrel

Chemical Property:

• Appearance/Colour: White Solid
• Vapor Pressure: 6.13E-11mmHg at 25°C
• Melting Point: 182-184 °C
• Refractive Index: 1.574
• Boiling Point: 473.1 °C at 760 mmHg
• PKA: 13.04±0.40(Predicted)
• Flash Point: 201.1 °C
• PSA: 37.30000
• Density: 1.13 g/cm³
• LogP: 4.04870
• Storage Temp.: -20°C
• Solubility.: DMSO: >5mg/mL
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 324.208930132
• Heavy Atom Count: 24
• Complexity: 677

Purity/Quality:

99% ^*data from raw suppliers

Etonogestrel ^*data from reagent suppliers

Safty Information:

• Statements: 60-40

MSDS Files:

Useful:

• Canonical SMILES: CCC12CC(=C)C3C(C1CCC2(C#C)O)CCC4=CC(=O)CCC34
• Isomeric SMILES: CC[C@]12CC(=C)[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=CC(=O)CC[C@H]34
• Recent ClinicalTrials: Breastfeeding Etonogestrel Implant Study
• Recent EU Clinical Trials: A Phase I, Open-Label Study to Investigate the Pharmacokinetics and Pharmacodynamics of Etonogestrel (ENG) and 17?-Estradiol (E2) in Healthy female Postmenarcheal Adolescents and Healthy Female Adults Following Administration of MK-8342B (ENG-E2, 125/300 μg/day) Vaginal Ring
• Uses: A biologically active metabolite of Desogestrel.

Technology Process of Etonogestrel

There total 28 articles about Etonogestrel which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

13β-ethyl-17α-hydroxy-11-methylene-, cyclic 1,2-ethanediyldithioacetal-18,19-dinorpregn-4-en-20-yn-3-one → etonogestrel (54048-10-1)

Guidance literature:

With water; In tetrahydrofuran; methanol; at 2 ℃; for 2.5h; Concentration; Reagent/catalyst; Solvent; Time; Temperature;

Reference yield: 62.0%

Acetic acid (8S,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-11-methylene-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester (187538-71-2) → etonogestrel (54048-10-1)

Guidance literature:

With sodium hydroxide; In methanol; for 3h; Ambient temperature;

DOI:10.1016/S0040-4020(01)89263-2

Reference yield:

C25H40O3Si + trimethylsilylacetylene (1066-54-2) → etonogestrel (54048-10-1)

Guidance literature:

trimethylsilylacetylene; With n-hexyllithium; In tetrahydrofuran; n-heptane; at -5 ℃; for 0.5h;

C₂₅H₄₀O₃Si; In tetrahydrofuran; n-heptane; for 15h; Further stages;

upstream raw materials:

Acetic acid (8S,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-11-methylene-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

desogestrel

18a-homo-estr-4-ene-11α,17β-diol

11-methylene-18a-homo-estr-4-en-17-one

Downstream raw materials:

3alpha-Hydroxydesogestrel

13-ethyl-11-methylene-18,19-dinor-17α-pregn-4-en-20-yne-3β-17β-diol

Refernces

• 1、 -. "COMBINED SYNTHESIS ROUTE FOR ETONOGESTREL AND DESOGESTREL". . . Retrieved 2013/09/26.
• 2、 -. "Pharmaceutical combined preparation, kit and method for hormonal contraception". . . Retrieved 2008/06/13.