Pharmakon1600-01503831

Base Information

• Chemical Name: Pharmakon1600-01503831
• CAS No.: 67392-87-4
• Molecular Formula: C₂₄H₃₀O₃
• Molecular Weight: 366.5
• Hs Code.: 2937230000
• NSC Number: 760103
• ChEMBL ID: CHEMBL313503
• Mol file: 67392-87-4.mol

Synonyms:Pharmakon1600-01503831;SCHEMBL881101;CHEMBL313503;HMS3264D07;NSC760103;CCG-213203;AB01563285_01

Chemical Property of Pharmakon1600-01503831

Chemical Property:

• Appearance/Colour: Off-white crystalline powder
• Vapor Pressure: 3.07E-12mmHg at 25°C
• Melting Point: 196-200 °C
• Refractive Index: 1.61
• Boiling Point: 552.2 °C at 760 mmHg
• Flash Point: 241.6 °C
• PSA: 43.37000
• Density: 1.26 g/cm³
• LogP: 4.30590
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO: ≥15
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 366.21949481
• Heavy Atom Count: 27
• Complexity: 828

Purity/Quality:

99.00% ^*data from raw suppliers

Drospirenone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 60
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(=O)C=C1C3CC3C4C2CCC5(C4C6CC6C57CCC(=O)O7)C
• Isomeric SMILES: C[C@]12CCC(=O)C=C1[C@@H]3C[C@@H]3C4C2CC[C@]5(C4[C@@H]6C[C@@H]6[C@@]57CCC(=O)O7)C
• Description: Drospirenone is a synthetic progestogen that binds to the progesterone, mineralocorticoid, and androgen receptors with binding affinities of 20, 230, and 65% relative to R5020, aldosterone , and R1881, respectively. In vivo, drospirenone inhibits spontaneous ovulation in rats (ID50s = 0.3-1.0 mg/day) when administered orally or subcutaneously. Drospirenone (0.5 mg/animal) administered six times per day maintains pregnancy in ovariectomized pregnant rats. It reduces serum testosterone (Item Nos. 15645 | ISO60154) and luteinizing hormone in cynomolgus monkeys in a dose-dependent manner. Drospirenone (10 mg/animal per day) also inhibits testosterone-induced growth of the seminal vesicles and prostate in castrated rats. Formulations containing drospirenone have been used as oral contraceptives. The steroid drospirenone in combination with the estrogen agonist ethinylestradiol was introduced in Germany as a new oral contraceptive for women. This analog of the aldosterone antagonist spironoiactone can be synthesized in five steps from 3β-hydroxy- 15β,16β-methylene-5-androsten-l7-one. Since its binding profile for steroid receptors is very similar to progesterone, drospirenone mimics the progestogen agonistic activity as well as the anti-androgenic and anti-mineralocorticoid properties of the endogenous hormone. In rats, drospirenone inhibited ovulation at 6.3 mglkglday p.o. Compared with currently available progestins which lack anti-mineralocorticoid activity, drospirenone did not cause weight gain that could result from fluid retention in clinical studies. Its combination with ethinylestradiol was well tolerated and did not engender adverse effects on blood pressure or plasma lipid levels. Drospirenone is rapidly absorbed in man with an oral bioavailability of 76%. It is extensively metabolized since over 20 different metabolites were observed in the urine and in the feces, resulting for instance from hydrolysis of the lactone in the plasma or reductive conjugation of the enone to the 3-sulfate ester of 45 dihydrodrospirenone. Its elimination is bi-exponential with an initial and a terminal half-life of 2 and 25-33h respectively.
• Uses: Synthetic progestogen exhibiting antimineralocorticoid and antiandrogenic activity. anti-cancer therapeutic Drospirenone has been used as a progestogen agent in pond snail and fish.
• Therapeutic Function: Aldosterone antagonist

Technology Process of Pharmakon1600-01503831

There total 59 articles about Pharmakon1600-01503831 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: 92.62%

C26H38O5 (1248589-68-5) → dihydrospirorenone (90457-65-1,93920-59-3,67372-75-2,67392-87-4)

Guidance literature:

C₂₆H₃₈O₅; With potassium hydroxide; In methanol; water; at 60 ℃; for 2.5h; Reflux;

With water; acetic acid; In methanol; at 50 - 60 ℃; Product distribution / selectivity; Cooling with ice;

Reference yield: 90.0%

6β,7β;15β,16β-dimethylene-3-oxo-17α-pregn-4,20-diene-21,17-carbolactone → dihydrospirorenone (90457-65-1,93920-59-3,67372-75-2,67392-87-4)

Guidance literature:

With hydrogen; platinum on carbon; In ethyl acetate; for 1h; under 75.0075 Torr; Inert atmosphere;

Reference yield: 82.0%

6β,7β;15β,16β-bismethylene-3-oxoandrost-4-ene[17(β-1')spiro-5']-perhydrofuran-2'ε-ol methyl ether (889652-27-1) → dihydrospirorenone (90457-65-1,93920-59-3,67372-75-2,67392-87-4)

Guidance literature:

6β,7β;15β,16β-bismethylene-3-oxoandrost-4-ene[17(β-1')spiro-5']-perhydrofuran-2'ε-ol methyl ether; With Jones reagent; In acetone; at 0 - 5 ℃; for 1h;

With isopropyl alcohol; In water; acetone; at 0 - 5 ℃; for 0.5h; Product distribution / selectivity;

upstream raw materials:

17α-(3-hydroxypropyl)-6β,7β;15β,16β-dimethylene-5β-androstane-3β,5,17β-triol

3-(17β-hydroxy-6β,7β;15β,16β-dimethylene-3-oxo-4-androstene-17β-yl)propionic acid γ-lactone

C₂₅H₃₀O₅

3β-hydorxy-15β,16β-methylene androst-5-ene-17-one

Downstream raw materials:

7β-chloromethyl-15β,16β-methylene-3-oxo-17β-pregn-4-ene-21,17-carbolactone

7β-chloromethyl-15β,16β-methylene-3-oxo-17α-pregn-4-ene-21,17-carbolactone

Spirorenone

Refernces

• 1、 -. "A drospirenone and intermediate preparation method (by machine translation)". Paragraph 0098-0104. . Retrieved 2019/11/20.
• 2、 -. "PROCESS FOR THE PREPARATION OF DROSPIRENONE". Page/Page column 11. . Retrieved 2014/10/29.