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% purity, *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.
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Uses
Synthetic progestogen exhibiting antimineralocorticoid and antiandrogenic activity. anti-cancer therapeutic Drospirenone has been used as a progestogen agent in pond snail and fish.
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Therapeutic Function
Aldosterone antagonist
