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SML0147

Sigma-Aldrich

Drospirenone

≥98% (HPLC)

Synonym(s):

6β,7β:15β,16β -Dimethylene-3-oxo-17α-pregn-4-ene-21,17-carbolactone, Dihydrospirorenone

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About This Item

Empirical Formula (Hill Notation):
C24H30O3
CAS Number:
67392-87-4
Molecular Weight:
366.49
EC Number:
266-679-2
MDL number:
MFCD00867350
UNSPSC Code:
51111800
PubChem Substance ID:
329825195
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D -180 to -195°, c = 1 in methanol

storage condition

desiccated

color

white to tan

solubility

DMSO: ≥15

originator

Bayer

storage temp.

2-8°C

SMILES string

C[C@]12CCC(=O)C=C1[C@@H]3C[C@@H]3[C@@H]4[C@@H]2CC[C@@]5(C)[C@H]4[C@@H]6C[C@@H]6[C@@]57CCC(=O)O7

InChI

1S/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

InChI key

METQSPRSQINEEU-HXCATZOESA-N

Gene Information

human ... NR3C2(4306) , PGR(5241)

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Application

Drospirenone has been used as a progestogen agent in pond snail and fish.
Drospirenone was tested for genotoxicity in rat and human hepatocytes.

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.

Features and Benefits

This compound is featured on the Nuclear Receptors (Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Bayer. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H360

Precautionary Statements

P201 - P308 + P313

Hazard Classifications

Repr. 1B

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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The use of combined estrogen/progesterone has been shown to result in an increased cardiovascular risk in randomised double-blinded trials. However, these studies used oral progestogen (progestin) preparations, which lack anti-mineralocorticoid activity and have suboptimal anti-androgenic activity compared with progesterone. Drospirenone
C Q Wu et al.
BJOG : an international journal of obstetrics and gynaecology, 120(7), 801-810 (2013-03-28)
Previous studies have provided conflicting results regarding the effect of drospirenone-containing oral contraceptive pills (OCPs) on the risk of venous and arterial thrombosis. To conduct a systematic review to assess the risk of venous thromboembolism (VTE), myocardial infarction (MI), and
Laureen M Lopez et al.
The Cochrane database of systematic reviews, (2)(2), CD006586-CD006586 (2009-04-17)
Premenstrual syndrome (PMS) is a common problem. Premenstrual dysphoric disorder (PMDD) is a severe form of PMS. Combined oral contraceptives (COCs), which have both progestin and estrogen, have been examined for their ability to relieve premenstrual symptoms. A COC containing
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