Desogestrel

Base Information

• Chemical Name: Desogestrel
• CAS No.: 54024-22-5
• Molecular Formula: C22H30O
• Molecular Weight: 310.48
• Hs Code.: 29372390
• European Community (EC) Number: 258-929-4
• UNII: 81K9V7M3A3
• DSSTox Substance ID: DTXSID6022898
• Nikkaji Number: J12.635G
• Wikipedia: Desogestrel
• Wikidata: Q415304
• NCI Thesaurus Code: C47476
• RXCUI: 22656
• Pharos Ligand ID: WDCUQ72V1T1M
• Metabolomics Workbench ID: 35403
• ChEMBL ID: CHEMBL1533
• Mol file: 54024-22-5.mol

Synonyms:13 Ethyl 11 methylene 18,19 dinor 17 alpha pregn 4 en 20 yn 17 ol;13-Ethyl-11-methylene-18,19-dinor-17 alpha-pregn-4-en-20-yn-17-ol;18,19-Dinorpregn-4-en-20-yn-17-ol, 13-ethyl-11-methylene-, (17alpha)-;alpha-pregn-4-en-20-yn-17-ol, 13-Ethyl-11-methylene-18,19-dinor-17;Cerazette;Desogestrel;Marvelon;Org 2969;Org-2969;Org2969

Chemical Property of Desogestrel

Chemical Property:

• Appearance/Colour: white to off-white crystalline powder
• Vapor Pressure: 3.92E-09mmHg at 25°C
• Melting Point: 109-110 ºC
• Refractive Index: 1.566
• Boiling Point: 428.3 ºC at 760 mmHg
• PKA: 13.07±0.40(Predicted)
• Flash Point: 187.9 ºC
• PSA: 20.23000
• Density: 1.07 g/cm³
• LogP: 4.86970
• Storage Temp.: -20°C Freezer
• Solubility.: Practically insoluble in water, very soluble in methanol, freely soluble in anhydrous ethanol and in methylene chloride.
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 310.229665576
• Heavy Atom Count: 23
• Complexity: 605

Purity/Quality:

99%min ^*data from raw suppliers

Desogestrel ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCC12CC(=C)C3C(C1CCC2(C#C)O)CCC4=CCCCC34
• Isomeric SMILES: CC[C@]12CC(=C)[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=CCCC[C@H]34
• Recent ClinicalTrials: Desogestrel for the Preoperative Treatment of Endometrioma Compared With Placebo
• Recent EU Clinical Trials: Multi-center, phase 2, open-label, randomized clinical trial to evaluate the inhibition of ovulation of 3 dosing strengths of levonorgestrel (LNG) vaginal delivery system (VDS), releasing during 28 days in continuous regimen, versus desogestrel (Cerazet?)
• Description: Desogestrel is a synthetic progestogen. It inhibits ovulation and prevents fertilization in rabbits and mice. Desogestrel inhibits rhodamine 123 efflux, a measure of P-glycoprotein activity, ex vivo in human lymphocytes and CD8+ T cells in a dose-dependent manner. Formulations containing desogestrel have been used as oral contraceptives and for the treatment of polycystic ovary syndrome.
• Uses: A progestogen with low androgenic potency
• Therapeutic Function: Progestin
• Clinical Use: Desogestrel also is a prodrug and is rapidly metabolized in the intestinal mucosa and on first pass through the liver to its active metabolite, etonogestrel (3-ketodesogestrel). Following oral administration, the relative bioavailability for desogestrel is approximately 84%. Desogestrel also exhibits high selectivity for the progesterone receptor and low and rogenic activity, and it does not diminish the beneficial effects of estrogen on the lipid profile.

Technology Process of Desogestrel

There total 53 articles about Desogestrel 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: 96.5%

C24H38O2Si → desogestrel (54024-22-5)

Guidance literature:

With hydrogenchloride; In methanol; water; Solvent; Reflux;

Reference yield: 89.0%

11-methylene-18a-homo-estr-4-en-17-one (54024-21-4) + trimethylsilylacetylene (1066-54-2) → desogestrel (54024-22-5)

Guidance literature:

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

11-methylene-18a-homo-estr-4-en-17-one; In tetrahydrofuran; hexane; at 0 - 5 ℃; for 1h;

Reference yield: 89.0%

lithium acetylide-ethylenediamine complex (1216963-74-4) + 11-methylene-18a-homo-estr-4-en-17-one (54024-21-4) → desogestrel (54024-22-5)

Guidance literature:

In dimethyl sulfoxide; at 20 ℃; for 21h;

upstream raw materials:

C₂₄H₃₂OS₂

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

acetylene

lithium acetylide-ethylenediamine complex

Downstream raw materials:

etonogestrel

Refernces

• 1、 -. "PROCESS AND NEW INTERMEDIATES FOR THE PREPARATION OF 11-METHYLENE STEROIDS". . . Retrieved 2017/09/19.
• 2、 -. "Desogestrel and its new process for preparation of the intermediate compounds". Paragraph 0050-0052. . Retrieved 2017/03/28.