ChemicalBook CAS DataBase List 67392-87-4

67392-87-4

Name	Drospirenone
CAS	67392-87-4
EINECS(EC#)	266-679-2
Molecular Formula	C24H30O3
MDL Number	MFCD00867350
Molecular Weight	366.49
MOL File	67392-87-4.mol

Chemical Properties

Appearance	Off-White Crystalline Powder
Melting point	196-200°C
alpha	-180 º (c=0.5, chloroform)
Boiling point	552.2±50.0 °C(Predicted)
density	1.26±0.1 g/cm3(Predicted)
storage temp.	-20°C Freezer
solubility	DMSO: ≥15
form	powder
color	white to tan
Optical Rotation	[α]/D -180 to -195°, c = 1 in methanol
InChIKey	METQSPRSQINEEU-URUUTGNFNA-N
SMILES	C[C@]12CC[C@]3([H])[C@]4(CCC(=O)C=C4[C@@H]4C[C@@H]4[C@@]3([H])[C@]1([H])[C@@H]1C[C@@H]1[C@]12CCC(=O)O1)C \|&1:1,4,6,13,15,16,18,20,22,23,r\|

Safety Data

Symbol(GHS)	GHS08
Signal word	Danger
Hazard statements	H360
Precautionary statements	P201-P202-P280-P308+P313-P405-P501
Hazard Codes	T
Risk Statements	60 less more
Safety Statements	36/37 less more
WGK Germany	3
RTECS	WH1299000
HS Code	2937230000
Hazardous Substances Data	67392-87-4(Hazardous Substances Data)

Hazard Information

Chemical Properties

Off-White Crystalline Powder

Uses

anti-cancer therapeutic

Uses

antiviral

Uses

Synthetic progestogen exhibiting antimineralocorticoid and antiandrogenic activity.

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 (Item No. 15273), 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.

Description

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.

Originator

Schering AG (Germany)

Definition

ChEBI: Drospirenone is a steroid lactone and a 3-oxo-Delta(4) steroid. It has a role as a contraceptive drug, an aldosterone antagonist and a progestin.

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).

Brand name

Yasmin

Therapeutic Function

Aldosterone antagonist

General Description

Drospirenone, 3-oxo-6β,7β:15β,16β-dimethylene-17α-pregn-4-en-21,17-carbolactone,differs structurally from all the other commercially availableprogestins. Its structure is similar to that of spironolactone,an MR antagonist, and it does have antimineralocorticoidactivity as well as progestational activity. It isalso reported to have some antiandrogenic effects. Thespirolactone at C17 and the two cyclopropyl groups at C6-C7 and C15-C16 contribute to these unique actions.Drospirenone is the progestin component in the newer oralcontraceptives, Yasmin and Yaz, and in the HRT product,Angeliq.

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.

References

[1] K. POLLOW . Dihydrospirorenone (ZK30595): A novel synthetic progestagen-characterization of binding to different receptor proteins[J]. Contraception, 1992, 46 6: Pages 561-574. DOI: 10.1016/0010-7824(92)90121-9
[2] PETER MUHN. Drospirenone: A novel progestogen with antimineralocorticoid and antiandrogenic activity[J]. Contraception, 1995, 51 2: Pages 99-110. DOI: 10.1016/0010-7824(94)00015-o
[3] DAN APTER . Bleeding pattern and cycle control with estetrol-containing combined oral contraceptives: results from a phase II, randomised, dose-finding study (FIESTA)[J]. Contraception, 2016, 94 4: Pages 366-373. DOI: 10.1016/j.contraception.2016.04.015

Questions And Answer

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 Chemicalbook 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.;

Spectrum Detail

Supplier

Jiangxi ravel Biotechnology Co.,Ltd

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J & K SCIENTIFIC LTD.

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Wuhan Fortuna Chemical Co., Ltd

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BioBioPha Co., Ltd.

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S.Z. PhyStandard Bio-Tech. Co., Ltd.

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S.Z. PhyStandard Bio-Tech. Co., Ltd.

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Shanghai civi chemical technology co.,Ltd

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Beijing HuaMeiHuLiBiological Chemical

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Websitehttp://www.huabeibiochem.com/

Haoyuan Chemexpress Co., Ltd.

Telephone021-58950125

Websitehttp://gb.chemexpress.com.cn

9ding chemical ( Shanghai) Limited

Telephone4009209199

Websitehttp://www.9dingchem.com

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67392-87-4

Chemical Properties

Safety Data

Hazard Information

Chemical Properties

Uses

Uses

Uses

Description

Description

Originator

Definition

Manufacturing Process

Brand name

Therapeutic Function

General Description

Biochem/physiol Actions

References

Questions And Answer

Natural progesterone

Side effects of human estrogen

Spectrum Detail

Supplier

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