Dydrogesterone

Base Information

• Chemical Name: Dydrogesterone
• CAS No.: 152-62-5
• Molecular Formula: C₂₁H₂₈O₂
• Molecular Weight: 312.452
• European Community (EC) Number: 205-806-8
• NSC Number: 92336
• UNII: 90I02KLE8K
• DSSTox Substance ID: DTXSID1022974
• Nikkaji Number: J3.272G
• Wikipedia: Dydrogesterone
• Wikidata: Q4161380
• NCI Thesaurus Code: C65501
• Pharos Ligand ID: MDT3BD6DDGHH
• Metabolomics Workbench ID: 42746
• ChEMBL ID: CHEMBL1200853
• Mol file: 152-62-5.mol

Synonyms:6 Dehydro 9 beta 10 alpha progesterone;6-Dehydro-9 beta-10 alpha-progesterone;Dehydrogesterone;Duphaston;Dydrogesterone;Isopregnenone

Chemical Property of Dydrogesterone

Chemical Property:

• Vapor Pressure: 9.55E-09mmHg at 25°C
• Melting Point: 168-173 °C
• Refractive Index: 1.556
• Boiling Point: 462.8 °C at 760 mmHg
• Flash Point: 172.2 °C
• PSA: 34.14000
• Density: 1.1 g/cm³
• LogP: 4.49950
• Storage Temp.: Refrigerator
• Solubility.: Practically insoluble in water, soluble in acetone, sparingly soluble in ethanol (96 per cent).
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 312.208930132
• Heavy Atom Count: 23
• Complexity: 628

Purity/Quality:

99.00% ^*data from raw suppliers

Dydrogesterone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1CCC2C1(CCC3C2C=CC4=CC(=O)CCC34C)C
• Isomeric SMILES: CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@@H]3[C@H]2C=CC4=CC(=O)CC[C@@]34C)C
• Recent ClinicalTrials: Comparison of the Live Birth Rate Between the PPOS and the GnRH Antagonist Protocol in Patients Undergoing IVF
• Recent EU Clinical Trials: Dydrogesterone versus micronized vaginal progesterone (MVP) for luteal phase support (LPS) in hormone replacement therapy (HRT) frozen embryo transfer (FET) cycles.
• Recent NIPH Clinical Trials: The efficacy of progestin primed ovarian stimulation (PPOS) during controlled ovarian stimulation(COS) for patients with endometriosis
• Indications: Dydrogesterone is used for the treatment of a variety of indications, including threatened or recurrent miscarriage during pregnancy, dysfunctional bleeding, infertility due to luteal insufficiency, dysmenorrhea, endometriosis, secondary amenorrhea, irregular cycles, premenstrual syndrome, and as a component of menopausal hormone therapy[7].
• Description: Dydrogesterone is a synthetic progestogen that has no estrogenic, androgenic, glucocorticoid, or anabolic effects, although it is an agonist of progesterone receptors (EC50 = 12.3 nM) and an antagonist of androgen, mineralocorticoid, and glucocorticoid receptors (IC50s = 28.6, 82.7, and 363 nM, respectively). Dydrogesterone protects against sound stress-induced abortion in mice when administered at a dose of 1.25 mg per animal prior to the stressor on day five of pregnancy. Formulations containing dydrogesterone have been used in hormone replacement therapy, in the treatment of menstrual disorders, and to prevent miscarriage.
• Uses: central stimulant, convulsant A synthetic progestin largely used in hormone therapy, on the central nervous system by studying two markers of the neuroendocrine function: the neurosteroid allopregnanolone and the opioid .beta.-endorphin. Progestogen.
• Therapeutic Function: Progestin

Technology Process of Dydrogesterone

There total 29 articles about Dydrogesterone 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: 86.3%

7-Dehydro-9β,10α-progesteron (16484-70-1) → dydrogesterone (601-33-2,1162-56-7,2640-38-2,3795-24-2,25093-47-4,152-62-5)

Guidance literature:

With hydrogen bromide; acetic acid; at 0 ℃; Reagent/catalyst;

Reference yield:

(9β,10α)-pregn-4-ene-3,20-dione (2755-10-4) → dydrogesterone (601-33-2,1162-56-7,2640-38-2,3795-24-2,25093-47-4,152-62-5)

Guidance literature:

With chloranil; In tert-butyl alcohol; at 20 - 85 ℃; Reagent/catalyst; Temperature; Inert atmosphere;

Reference yield:

Progesterone (57-83-0) → dydrogesterone (601-33-2,1162-56-7,2640-38-2,3795-24-2,25093-47-4,152-62-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 20 - 120 °C

2.1: rhodium(III) chloride hydrate; sodium periodate / tetrachloromethane; acetonitrile; water

3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 20 - 80 °C

4.1: sodium tetrahydroborate; methanol / -55 °C

5.1: Rh/Al₂O₃; hydrogenchloride; hydrogen / water; ethanol / 20 °C

6.1: sodium hydroxide / tert-butyl alcohol / 0.5 h / 20 - 55 °C / Inert atmosphere

6.2: 1 h / 50 - 55 °C

7.1: chromium(VI) oxide; sulfuric acid / water; acetone / -10 - -5 °C

8.1: chloranil / tert-butyl alcohol / 20 - 85 °C / Inert atmosphere

With chromium(VI) oxide; hydrogenchloride; methanol; sodium tetrahydroborate; sodium periodate; rhodium(III) chloride hydrate; sulfuric acid; Rh/Al₂O₃; hydrogen; chloranil; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide; In tetrachloromethane; ethanol; water; acetone; toluene; acetonitrile; tert-butyl alcohol;

upstream raw materials:

7-Dehydro-9β,10α-progesteron

Des-A-17α-Δ⁹-pregnen-5,20-dion

(9β,10α)-pregn-4-ene-3,20-dione

Progesterone

Downstream raw materials:

9β,10α-Pregna-4,6,8(14)-trien-3,20-dion

Refernces

• 1、 -. "Method for synthesizing dydrogesterone". Paragraph 0029-0031. . Retrieved 2021/05/19.
• 2、 -. "PROCESS FOR PREPARATION OF DYDROGESTERONE". . . Retrieved 2018/09/08.