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Merck
CN

SML0147

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
NACRES:
NA.77
PubChem Substance ID:
329825195
UNSPSC Code:
51111800
EC Number:
266-679-2
MDL number:
MFCD00867350
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
100
Storage condition:
desiccated

Key Documents

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InChI key

METQSPRSQINEEU-HXCATZOESA-N

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

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

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

Quality Level

100

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.
Fourth-generation progestin; contraceptive

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

signalword

Danger

hcodes

H360

Hazard Classifications

Repr. 1B

Storage Class

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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000433220
0000197799
0000433220
0000175245
0000162924

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Antonietta Martelli et al.
Mutation research, 536(1-2), 69-78 (2003-04-16)
Sex steroids, due to the generally negative responses observed in routinely employed standard genotoxicity assays, are considered epigenetic carcinogens. Some doubts on this conviction are raised by the results of recent studies providing evidence that cyproterone acetate and two structural
Complex molecular changes induced by chronic progestogens exposure in roach, Rutilus rutilus
Maasz G, et al.
Ecotoxicology and Environmental Safety, 139, 9-17 (2017)
Kadriye Aydin et al.
Contraception, 87(3), 358-362 (2012-08-18)
Limited data are available regarding the potential effects of oral contraceptives (OCs) on body fat distribution particularly in lean women with polycystic ovary syndrome (PCOS). In the current study, we aimed to evaluate the influence of ethinyl estradiol and drospirenone
Apurva Motivala et al.
Drugs, 67(5), 647-655 (2007-03-28)
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
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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