Drospirenone

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Drospirenone
Systematic (IUPAC) name
(6R,7R,8R,9S,10R,13S,14S,15S,16S,17S)-
1,3',4',6,6a,7,8,9,10,11,12,13,14,15,15a,16-
hexadecahydro-10,13-dimethylspiro-
[17H-dicyclopropa-6,7:15,16]cyclopenta
[a]phenanthrene-17,2'(5H)-furan]-3,5'(2H)-dione)
Identifiers
CAS number 67392-87-4
ATC code G03AA12
PubChem 68873
Chemical data
Formula C24H30O3 
Mol. mass 366.493 g/mol
Pharmacokinetic data
Bioavailability 76%
Protein binding 97%
Metabolism Hepatic, minor (CYP3A4-mediated)
Half life 30 hours
Excretion Renal and fecal
Therapeutic considerations
Pregnancy cat.

X(US)
Legal status
Routes Oral

Drospirenone is a synthetic progestin that is an analog to spironolactone, with a molecular weight of 366.5 and the molecular formula C24H30O3.

Contents

[edit] Properties and uses

Drospirenone is part of certain birth control formulations. The compound differs from other synthetic progestins in that its pharmacological profile in preclinical studies shows it to be closer to the natural progesterone. As such it has anti-mineralocorticoid properties, counteracts the estrogen-stimulated activity of the renin-angiotensin-aldosterone system, and is not androgenic. With its activities similar to spironolactone it may lead to less water retention and breast tenderness while improving skin appearance (less acne).

Drospirenone is taken orally with about 76% bioavailability. It is bound not by sex hormone binding globulin or corticosteroid binding globulin, but by other serum proteins. Metabolites have not been shown to be biologically active, show up in urine and feces, and are essentially completely excreted within 10 days.

The compound is part of certain newer oral contraceptive formulations:

  • Yasmin contains 3 mg drospirenone and 30 mcg ethinylestradiol per tablet. It is indicated for the prevention of pregnancy in women who elect an oral contraceptive.
  • Yasminelle contains 3 mg drospirenone and 20 mcg ethinylestradiol per tablet and is used for contraception.
  • Yaz contains 3 mg drospirenone and 20 mcg ethinylestradiol per tablet and is given for 24/4 days with the same indications.

It has also been formulated in medication to manage menopausal symptoms using 0.5 mg drsp and 1 mg estradiol per day by oral application. This medication was introduced in the USA in 2007 as Angeliq.

Drospirenone at 3mg, which can potentially cause hyperkalemia in high-risk patients, is comparable to a 25mg dose of spironolactone.

The medication is contraindicated in patients with hepatic dysfunction, renal insufficiency, adrenal insufficiency, or in whom the use of oral contraceptives is contraindicated, such as smokers and patients with a history of DVT, stroke, or other blood clots. Because of the anti-mineralocorticoid effects care needs to be exercised when other drugs that may increase potassium levels are taken. Such medications include ACE inhibitors, angiotensin-II receptor agonists, potassium-sparing diuretics, potassium supplementation, heparin, aldosterone antagonists, and NSAIDs.

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v • d • e
Sex hormones and related agents (primarily G03, also L02, H01C) - human endogenous in CAPS
Progestogens:
(receptor)
Androgens:
(receptor)
Estrogens:
(receptor)
Gonadotropins:
(FSHR/LHCGR)
GnRH:
(receptor)