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Drospirenone, sold under the brand names Yasmin and Angeliq among others, is a progestin medication which is used in birth control pills to prevent pregnancy and in menopausal hormone therapy, among other uses.
Rare side effects of drospirenone may include high potassium levels and blood clots, among others. Drospirenone is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.
Drospirenone was introduced for medical use in 2000.
Contents
1 Medical uses
1.1 Available forms
1.1.1 Formulations
2 Contraindications
3 Side effects
3.1 High potassium levels
3.2 Blood clots
4 Overdose
5 Interactions
6 Pharmacology
6.1 Pharmacodynamics
6.1.1 Progestogenic activity
6.1.2 Antimineralocorticoid activity
6.1.3 Antiandrogenic activity
6.2 Pharmacokinetics
7 Chemistry
8 History
9 Society and culture
9.1 Generic names
9.2 Brand names
9.3 Availability
9.4 Litigation
10 Research
11 References
12 Further reading
13 External links
Medical uses
Drospirenone is an ingredient in some birth control pills and is used in menopausal hormone therapy. In combination with ethinylestradiol it is used as contraception, and for women who want contraception it is also approved by the U.S. Food and Drug Administration (FDA) to treat moderate acne and premenstrual dysphoric disorder.
Angeliq, a drospirenone and estradiol combination, has also been approved by the Food and Drug Administration (FDA) for treatment of moderate to severe vasomotor symptoms and/or vaginal atrophy associated with menopause.
The FDA has several approved indications for combined estrogen and drospirenone preparations. They are approved as a first-line therapy for menopausal symptoms such as the relief of hot flashes.
Available forms
Drospirenone is sold as a combined birth control pill under the brand names Yasmin (US, EU, Latin America), Jasmine (France), Yarina (Russia)
Formulations
See also: Oral contraceptive formulations
Drospirenone is a component of oral contraceptive formulations including the following:
Yasmin/Jamine/Yarina contains 3 mg drospirenone and 30 µg ethinylestradiol per tablet. It is indicated for the prevention of pregnancy in women who elect an oral contraceptive.
Safyral contains 3 mg drospirenone and 30 µg ethinylestradiol per tablet. It is indicated for the prevention of pregnancy in women who elect an oral contraceptive as well as to provide a daily dose of folate supplementation, which is recommended for women in their reproductive years. Folate lowers the risk of having rare neural tube birth defects in a pregnancy occurring during Safyral use or shortly after stopping.
Yaz/Gianvi/Vestura contains 3 mg drospirenone and 20 µg ethinylestradiol per tablet. It is indicated for prevention of pregnancy as well as treatment of premenstrual dysphoric disorder for women who choose to use an oral contraceptive for contraception. There has also been evidence for this formulation to treat moderate acne for women 14 years of age or older who choose to use an oral contraceptive for birth control.
A complete list of FDA approved oral contraceptives containing drospirenone as of October 2012: Beyaz (Drospirenone 3 mg, ethinylestradiol 0.02 mg and levomefolate calcium 0.451 mg), Drospirenone and ethinylestradiol (Drospirenone 3 mg and ethinylestradiol 0.03 mg), Gianvi (Drospirenone 3 mg and ethinylestradiol 0.02 mg), Loryna (Drospirenone 3 mg and ethinylestradiol 0.02 mg), Ocella (Drospirenone 3 mg and ethinylestradiol 0.03 mg), Safyral (Drospirenone 3 mg, ethinylestradiol 0.03 mg, and levomefolate calcium 0.451 mg), Syeda (Drospirenone 3 mg and ethinylestradiol 0.03 mg), Yasmin (Drospirenone 3 mg and ethinylestradiol 0.03 mg), Zarah (Drospirenone 3 mg and ethinylestradiol 0.03 mg), Yaz (Drospirenone 3 mg and ethinylestradiol 0.02 mg)
Contraindications
See also: Progestin § Contraindications
In addition to contraindications common to all combined estrogen–progestin medications, drospirenone-containing medications are contraindicated in women with severe renal insufficiency according to European Medicines Agency (EMA)-approved labels,
Side effects
High potassium levels
Drospirenone is an antimineralocorticoid with potassium -sparing properties, though in most cases no increase of potassium levels is to be expected.
Blood clots
While all oral contraceptives can increase the risk for venous thrombembolic events, including fatal blood clots, several studies have reported a greater risk for women taking contraceptives containing drospirenone. Women who take contraceptive pills containing drospirenone have a 6- to 7-fold risk of developing thromboembolism (dangerous blood clots) compared to women who do not take any contraceptive pill, and have twice the risk (some epidemiological studies suggest thrice, according to the FDA) compared to women who take a contraceptive pill containing levonorgestrel. However, the absolute risk is small, in the neighborhood of 9 to 27 out of 10,000 women on an oral contraceptive for a year (up to 9 for levonorgestrel vs up to 27 for drospirenone, or about 0.09% vs 0.3% per year).
When the U.S. Food and Drug Administration (FDA) became concerned about the risks of drospirenone, they funded studies based on the medical records of more than 800,000 women taking oral contraceptives. They found that the risk of VTE, which includes dangerous and potentially fatal blood clots, was 93% higher for women who had been taking oral contraceptives containing drospirenone for only 3 months or less and 290% higher for women taking drospirenone-containing oral contraceptives for 7 to 12 months, compared to women taking other types of oral contraceptives.
The FDA recently updated the label for contraceptives containing drospirenone to include warnings for stopping use prior to and after surgery, and to warn that contraceptives with drospirenone may have a higher risk of dangerous blood clots.
Overdose
See also: Progestin § Overdose
Interactions
See also: Progestin § Interactions
Pharmacology
Pharmacodynamics
Drospirenone binds with high affinity to the progesterone receptor (PR) and mineralocorticoid receptor (MR), with lower affinity to the androgen receptor (AR), and with very low affinity to the glucocorticoid receptor (GR).
Progestogenic activity
Drospirenone is an agonist of the PR, the biological target of progestogens like progesterone.
Antimineralocorticoid activity
Drospirenone is an antagonist of the MR, the biological target of mineralocorticoids like aldosterone, and hence is an antimineralocorticoid.
Antiandrogenic activity
Drospirorenone is an antagonist of the AR, the biological target of androgens like testosterone and dihydrotestosterone (DHT).
Pharmacokinetics
The oral bioavailability of drospirenone is between 76 and 85%.
Chemistry
See also: Spirolactone, List of progestogens, and List of steroidal antiandrogens § Spirolactone derivatives
v t e Chemical structures of spirolactones
Progesterone
Spirolactone
Canrenone
Spironolactone
Drospirenone
Spirorenone
Chemical structures of progesterone and spirolactones (steroid-17α-spirolactones).
Drospirenone, also known as 1,2-dihydrospirorenone or as 17β-hydroxy-6β,7β:15β,16β-dimethylene-3-oxo-17α-pregn-4-ene-21-carboxylic acid, γ-lactone, is a synthetic steroidal 17α-spirolactone, or more simply a spirolactone.
The loss of the C7α acetylthio group of spironolactone, a compound with negligible progestogenic activity,
History
Drospirenone was introduced for medical use in 2000.
Society and culture
Generic names
Drospirenone is the generic name of the drug and its INN, USAN, BAN, and JAN, while drospirénone is its DCF.
Brand names
Drospirenone is marketed in combination with an estrogen under a variety of brand names throughout the world.
Availability
Drospirenone is marketed widely throughout the world.
Litigation
In July 2012, Bayer notified its stockholders that there were more than 12,000 lawsuits against the company involving Yaz, Yasmin, and other oral contraceptives with drospirenone, and that the company by then settled 1,977 cases for US$402.6 million, for an average of US$212,000 per case, while setting aside US$610.5 million to settle the others.
As of July 17, 2015, there have been at least 4,000 lawsuits and claims still pending regarding venous thromboembolic events. This doesn’t include the roughly 10,000 claims that Bayer has already settled without admitting liability. These claims of venous thromboembolic events have amounted to US$1.97 billion. Bayer also reached a settlement for arterial thromboembolic events, including stroke and heart attacks, for US$56.9 million.
Research
Drospirenone (developmental code name LF-111) is or was under development by Leon Farma as a progestin-only pill for hormonal birth control in women, but as of March 2017 no recent reports of development have been identified.
Drospirenone (tentative brand name Estelle) is under development by Mithra Pharmaceuticals in combination with estetrol as a combined oral contraceptive for pregnancy in women.

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