67392-87-4 Usage
Description
Drospirenone is a synthetic progestogen that exhibits antimineralocorticoid and antiandrogenic activity. It binds to progesterone, mineralocorticoid, and androgen receptors with varying binding affinities. In vivo, it inhibits spontaneous ovulation in rats and maintains pregnancy in ovariectomized pregnant rats. It also reduces serum testosterone and luteinizing hormone in cynomolgus monkeys in a dose-dependent manner. Formulations containing drospirenone have been used as oral contraceptives.
Used in Pharmaceutical Industry:
Drospirenone is used as an oral contraceptive agent for women, in combination with the estrogen agonist ethinylestradiol. It mimics the progestogen agonistic activity as well as the anti-androgenic and anti-mineralocorticoid properties of the endogenous hormone, making it a suitable component in birth control formulations.
Used in Cancer Therapy:
Drospirenone is used as an anti-cancer therapeutic agent, potentially offering treatment options for various types of cancer.
Used in Aquaculture:
Drospirenone has been used as a progestogen agent in pond snail and fish farming, likely for hormonal regulation and growth promotion purposes.
Natural progesterone
Drospirenone is the only progesterone that has the characteristics similar to the natural progesterone currently, its structure is more like that of the natural progesterone compare with the structure of the progesterone contained in the traditional oral contraceptives.
Except the effect of anti-androgen, drospirenone has the role of anti-mineralocorticoid which can prevent water and sodium retain in the body. Not only it has the a great effectivenes of contraception, there are also many good impacts on women's health like reducing the acne, making the skin more smooth and controling the weight efficaciously.
Information on the use of oral contraceptives, drospirenone, side effects and other information edited by lookchem maggie.
Side effects of human estrogen
Drospirenone is a new synthetic progestin designed to mimic the effects of progesterone, it is the preogesterone which the pharmacological properties is closet to that of the natural progesterone, its also has the advantages of both salt corticosteroids and anti-androgen.
As a birth control hormones， Its can reduce the risk of pregnency by imitating progesterone, and increasing the levels of hormones. Therefore drospirenone is promoted as an effective contraception. However, since it has entered the market, drospirenone displays a negative impact on the female estrogen. When two hormones are mixed together, it would bring some bad influence to people.
When drospirenone reacts with estrogen, it can cause the blood thicken. It looks not like a big problem, but the blood clotting would lead to the formation of the thrombosis. The gore forming in the veins can impede blood flow or even plug in some vital organs like the heart, brain and lungs etc when it flowing. The thrombosis would Interference the heart from receiving blood which can cause a heart attack. If it affect the blood flow in brain, it would resulting in a stroke.
There is a possibility of side effects for any women who take the drospirenone, but the people who is obesity, smoking, depression, and have some diseases like the diabetes and high blood pressure are more likely to form the thrombosis when they take the contraception contained the drospirenone.
Originator
Schering AG (Germany)
Manufacturing Process
2.75 g of trimethyl sulfoxonium iodide is stirred in 57 ml of dimethyl sulfoxide
with 341 mg of 80% sodium hydride oil suspension for 2 h at room
temperature. The almost clear solution is combined under nitrogen with 2.0 g
of 15α,16α-methylene-3-oxo-4,6-androstadiene-[17(β-1')-spiro-
5']perhydrofuran-2'-one and agitated for 24 h at room temperature. The
mixture is then stirred into ice water, the thus-obtained precipitate is filtered
off, washed with water, and taken up in methylene chloride. After drying and
evaporation, the residue is purified by repeated preparative layer
chromatography, thus obtaining 520 mg of 6β,7β,15α,16α-dimethylene-3-oxo-
4-androstene-[17(β-1')-spiro-5']perhydrofuran-2'-one (drospirenone).
Therapeutic Function
Aldosterone antagonist
Biochem/physiol Actions
Drospirenone is a fourth-generation progestin that has antimineralocorticoid, and antiandrogenic activity in addition to potent progestogenic activity. In two recent studies drospirenone appeared to double the risk of venous thromboembolism compared to levonorgestrel, although other studies found little added risk.
Check Digit Verification of cas no
The CAS Registry Mumber 67392-87-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,7,3,9 and 2 respectively; the second part has 2 digits, 8 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 67392-87:
(7*6)+(6*7)+(5*3)+(4*9)+(3*2)+(2*8)+(1*7)=164
164 % 10 = 4
So 67392-87-4 is a valid CAS Registry Number.
InChI:InChI=1/C24H30O3/c1-22-6-3-12(25)9-17(22)13-10-14(13)20-16(22)4-7-23(2)21(20)15-11-18(15)24(23)8-5-19(26)27-24/h9,13-16,18,20-21H,3-8,10-11H2,1-2H3/t13-,14+,15-,16+,18+,20-,21+,22-,23+,24+/m1/s1
67392-87-4Relevant articles and documents
Synthetic method of drospirenone
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, (2021/09/15)
The invention provides a synthetic method of drospirenone. Belong to organic synthesis field. A compound having the structure shown in the formula II is obtained, 17-bit hydroxyl group is oxidized to a carbonyl group under the action of a noble metal catalyst and a persulfate, and the hydroxyl group on the III-position propyl group is oxidized into an aldehyde group, and then a hydroxyl aldehyde condensation forms a five-membered carboxylic acid lactone ring to obtain a compound having the structure shown 17 α in the formula IV 3. The compound drospirenone with the structure shown I is obtained, most of the raw materials are cheap, the high-pressure catalytic hydrogenation and is omitted, and meanwhile, the yield can reach 77% under mild reaction conditions. Drospirenone with a purity 99.6%.
PROCESS FOR THE PREPARATION OF DROSPIRENONE
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Page/Page column 7; 8; 9; 10, (2014/09/03)
A process is described wherein, by employing 17a-(3-hydroxypropyl) -63,7β3;15β,16β-dimethylene-5β-androstane-3β,5,17β-triol (II) as starting product, in a single stage reaction there is obtained drospirenone, (I), whereby the reaction is achieved using gaseous oxygen as the stoichiometric oxidant in the presence of a catalytic system containing (i) TEMPO or a derivative thereof, (ii) a ferric salt (Fe3+) and (iii) NaCI. The product drospirenone is a known synthetic steroid with progestogenic, antimineralocorticoid and antiandrogenic action, that is useful for preparing pharmaceutical compositions with contraceptive action.
Process for the preparation of drospirenone
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Paragraph 0031; 0032; 0033; 0034; 0035; 0036; 0037; 0038, (2013/06/06)
It is described a process for the preparation of Drospirenone, a synthetic steroid with progestogenic anti-mineralocorticoid and antiandrogenic activity having the formula 1 shown below, useful in the preparation of contraceptive pharmaceutical compositions, starting from 17α-(3-hydroxypropyl)-6β,7β;15β,16β-dimethylene-5β-androstan-3β,5,17β-triol.
